DGT MH –CET 12th CHEMISTRY Study Material 1

11 Alcohols, Phenols and Ethers

SECTION-I: ALCOHOLS STRUCTURE OF -OH GROUP IN

INTRODUCTION ALCOHOL
Definition of alcohol: These are hydroxy In alcohols, oxygen atom of the –OH group is
derivatives of hydrocarbons obtained by replacing attached to sp 3 hybridised carbon atom, by
one or more hydrogen atoms from corresponding overlapping of sp3 hybrid orbital of carbon and
hydrocarbons obtained by hydroxy groups. p-orbital of oxygen i.e., sp3 -p overlapping.
ISOMERISM IN ALCOHOLS The bond angle C—O—H is slightly less than
Monohydric alcohols : They shows chain, position the tetrahedral angle. It is due to repulsion of lone
optical isomerism themselves and functional pair electrons of the oxygen atom.
isomerism with ethers. Total number of isomefic 
alcohols can be calculated by formula, I = 2n–2.  O
Ethers : They shows metamerism, optical isomerism C H
themselves and functional isomerism with alcohols. PREPARATION METHODS
Total number of isomeric ethers can be calculated 1. Alkaline hydrolysis of alkyl halides :
formula, I = 2n–1 – 1 – (2n–2) from C3 onwards.
Total number of isomeric alcohols and ethers can R  X  NaOH 
aq.
 R  OH  NaX
calculated by formula, I = 2n–1 – 1. 2. From hydration of alkene (Olefin) by
(i) C2H6O (2-isomers) using conc. H2SO4 :
(a) CH 3CH 2OH ethyl alcohol
CH 2  CH 2  H 2SO 4
(b) CH3OCH\ dimethyl ether ethylene conc.

(ii) C3H8O (3-isomers. 2 alcohols, 1 ether)

Alcohols- 
cold
 CH 3  CH 2  OSO3 H
ethyl hydrogen sulphate
(a) CH 3CH 2CH 2OH n-propyl alcohol
(b) CH3CHOHCH3 iso-propyl alcohol CH3  CH 2  OSO3 H  H 2 O 
boil

Ether -
a) CH 3OC 2H 5 ethyl methyl ether CH 3  CH 2  OH  H 2SO 4
ethyl alcohol
(iii) C4H10O (7-isomers. 4 alcohols, 3 ethers)
Alcohols- Mechanism :
(a) CH3CH2CH2CH2OH n-butyl alcohol The mechanism of reaction involves three steps.
(b) (CH3)2CHCH2OH isobutyl alcohol Step-
(c) CH3CH2CHOHCH3 20 butyl alcohol (i) Protonation of water followed by attack of
(d) (CH 3) 3COH 30 butyl alcohol electrophilic H3O+ to form carbocation.
'a' and 'b' are chain isomers.
'a' and 'c' are position isomers. Only 'c' show H 2 O  H  
 H 3O 
optical isomerism.
Ethers-Following ethers are metamers.
Ethers-Following ethers are metamers.
(a) C 2H 5OC 2H 5 diethyl ether (ii) Nucleophilic attack of water on carbocation.
(b) CH3OCH2CH2CH3 methyl n-propyl
ether H H H
|   | | |
(c) CH3OCH(CH3)2 methyl isopropyl CC  H2 O

C  C  O H
| 
ether

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Alcohols, Phenols and Ethers 2

(iii) Deprotonation to form alcohol CH3
H H |
H CH3  C  CH 2  OH
| | | | | 
|
C  C  O H  H 2 O 
 C  C  OH  H 3 O CH3


3. By hydroboration oxidation of alkenes 4. From reduction of carbonyl compounds:

(HBO Reaction of alkenes) : (I) By the reduction of aldehydes and
ketones :
e.g.
Aldehydes on reduction gives 10 alcohols.
(i) 2CH2 = CH2 + (H–BH2)2
While ketones on reduction gives 2°
alcohols. These are reduced by two

THF
 2CH 3  CH 2  BH 2
ethyl boron methods.
CH3 – CH2 – BH2 + CH2 = CH2 (i) Catalytic hydrogenation in the presence
of nickel or raney nickel or raney nickel

 (CH 3  CH 2 ) 2 BH platinum or palladium as catalyst at
diethyl boron
413 K to 453 K. Raney nickel is an
alloy of aluminium and nickel (50%)
(CH 3  CH 2 ) 2 BH  CH 2  CH 2
diethyl boron leached by NaOH solution.
(ii) Reduction by using Na Hg + H2O or

 (CH 3  CH 2 ) 2 B NaBH4. of Na + ethanol or Zn + HC1
triethyl boron
or LiAIH4 or B2H6 a reducing agents.
(CH 3  CH 2 )3 B  3 HO . OH (a) Catalytic hydrogenation by using
H2 and Ni or Pt or Pd art 413 K :

NaOH
 3CH3  CH 2  OH  B(OH)3 When aldehydes and ketones are
CH 3 reduced by passing H2 gas in presence
| of Ni or raney Ni or Pt or Pd catalyst
(ii) CH 3  C  CH 2 
(i) B2 H 6 in THF
(ii) H 2 O2 , NaOH
 at 413 K to 453 to give alcohols, which
|
CH 3 affect unsaturation.
 C  O  H 2 
Ni 413 K
  CH  OH
CH 3 (b) Reduction by using NaHg + H2O
|
CH 3  C  CH 2  OH (Bouveault Blanc reduction) :
| When aldehydes and ketones are
CH 3 reduced by Na . Hg + H2O LiAlH4 or
NaBH4 give alcohols.
Note:
(i) The overall process occurs with addition of H2O Na. Hg  H 2 O 
 NaOH  Hg  [X]
by anti Markownikoffs rule. Boron is electron NaHg  H 2 O
 C  O  2[H]    CH  OH
deficient compound and behave as electrophiles.
Note : LiAlH4 or B2H6 or NaBH4 does
(ii) The good yield of primary alcohols is
not reduce > C = C < C <,  C1 C-bonds.
obtained by this method.
II. By reduction of carboxylic acids :
(iii) In hydroboration oxidation (HBO) process,
the carbocation are not formed hence no R – COOH + 4[H]
rearrangement takes place. 
LiAlH 4 / Ether
 R  CH 2  OH  H 2 C
H O
3
(iv) 10, 20, 30 alcohol can be obtained by this
method. III. By reduction of esters :
Esters are reduced by LiAlH4 or by passing
CH 3 hydrogen gas in the presence of catalyst like
|
CH 3  C  C   CH 2 
(i) B3 H 6 in THF
 Ni or Pt or Pd or raney Ni to give mixture
(ii) H 2 O 2 , NaOH
| of alcohol. But it is easily reduced by LiAlH4
CH 3 in ether because it is more reactive.

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Alcohols, Phenols and Ethers 3

REACTIVITY OF ALCOHOLS
O
|| Alcohols under goes two type of reactions:
R  C  OR ' 2H 2 
NI

Breaking of O–H bond (Acidity of Alcohols):
R – CH2 – OH + R' – OH The acidic character of alcohols is due to polar
5. From Grignards reagent (From action nature of OH bond. An electron releasing groups
of R – MgX on carbonyl compounds) (+I effect) increases electron density on oxygen
leading to decrease the polarity of — O — H
Preparation of 10 alcohols :
bond. This decrease the acidic strength. Therefore
H H acidity of alcohol is, 10 > 20 > 30.
| |
H  C  O  RMgX 
dry ether
 H  C  O  MgX The decreasing order of acidic strength of alcohol
|
R is
Mg  complex
R
R
H H 2 O R CH 2  OH  CH  OH  R C  OH
R
|
H  C  O  MgX  H 2O R
|
R Alcohols are weaker acidic than water
Mg  Complex

R  O   H  O  H 
 R  OH  OH 
H alkoxide base water acid conjugate acid conjugate base
 R  CH 2  OH  MgXOH
Pr imary Alcohol This reaction shows that, water is better proton
Preparation of secondary alcohols donor than alcohols.
Alkoxide ion is better proton accepter than
H hydroxide ion, which suggest that sodium alkoxides
|
R  C  O  RMgX are stronger base than NaOH.
Breaking of C—O bond: Electron releasing
H groups (+1 effect) increases electron density on
| carbon leading to increase the polarity of –C–O

 R  C  O  RMgX
dry ether
bond. This increase the reactivity of alcohols.
|
R Therefore reactivity of alcohol is, 30 > 20 > 1.
Mg  complex
CHEMICAL PROPERTIES
Alcohols undergo following types of reactions:
H
| Reaction involving breaking of O–H bond.
H  C  O  MgX  H 2 O
| Reaction involving breaking of C–O bond.
R Reaction involving breaking both alkyl and group
Mg  complex
O–H.


H
 R  CH 2  OH  MgXOH Reaction involving breaking of O–H bond :
Sec. R Alcohol Reaction with metals :
Preparation of tertiary alcohols: 2R  OH  2 Na 
 2R  ONa  H 2
alcohol sod. alkoxide
R R
| |
R  C  O  RMgX 
dry ether
 R  C  OH  MgX 6R  OH  2 NaI 
 2(R  O)3 Al  3H 2
| alcohol alu min ium alkoxide
R
Mg  complex
This reaction involving cleavage of oxygen
R R
hydrogen bond (–O–H) such type of reaction
|
H
| follows the order, 10 alco. > 20 alco. > 30 alco.
R  C  O  MgX  H 2 O   R  C  OH  MgXOH
| | Tertiary alcohols are almost inert to sodiun metal
R R
ter. alcohol and aluminium metal.

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Alcohols, Phenols and Ethers 4

(b) Reaction with carboxylic acid, acid chloride Alcohols are dehydrated by cone. H2SO4
and acid unhydride (ester formation): or A12O3 or H3PO4 or P2O5 or KHSO4 or
H ThO 2 or Boric acid (H3BO 3). Ease of
R 'OH  R  COOH R  COO  R ' H 2 O

dehydration is, 30 > 20 > 10 alcohols.
H
R ' OH  (R  CO) 2 O R  COOR ' RCOOH
(a) Dehydration by using cone. H 2 SO 4
H
R ' OH  R  COCl R  COO  R ' HCl (liquid phase dehydration): Alcohols
Reaction involving breaking of C–O bond : which do not contain  -H atom on
dehydration gives alkene through
1. Reaction with conc. HX :
rearrangement reaction in the presence of
(a) Reaction with conc. HCI (Grooves acid only.
Process): Reaction with cone. HCI in the
presence of anhydrous ZnCl2 with alcohol is CH 3
known as Lucas test. This test is used to |
distinguish between 10, 20, 30 alcohols. CH 3  C  CH 2  OH 
75 % H 2SO 4
423 K

|
R  OH  HCl 
Anhydrous ZnCl 2
 R  Cl  H 2 O CH 3
conc.  neo  pentyl alcohol

(b) Reaction with conc. HBr :

NaBr  conc. H 2SO4 CH 3
R  OH  HCl refluxed
 |
CH 3  C  CH  CH 3  H 2 O
R–Br + H2O 2  methyl 2  butene

Note: In the capse of HBr, a small amount

This reaction can be proceeding through
of concentrated H2SO4 is also added for the
following steps —
reaction with primary alcohols. But no
catalyst is added with secondary and tertiary CH 3
alcohols, which get dehydrated in the |
presence of concentrated H2SO4. CH 3  C  CH 2  OH 
Dehydration
H 2SO 4
|
(c) Reaction with conc. HI: CH 3
Mechanism of action of HX:
Step-I: Formation oxocation by protonation CH 3
|
of alcohol.  H2 O
CH 3  C  CH 2  O   
| |
H CH 3 H

| oxonium ion
R  O  H  H 
 R  O H

oxocation

Step-II: Loss of water from oxocation gives

carbocation.

H
|
 H2 O
R  O  H   R



Step-III : Action of X– on carbocation: CH 3  C  CH2 

H
 CH 3  C  CH  CH 3
| |
CH3 CH3
R   X  
 R X 30 pentyl 2  methyl 2  butene
carbonium ion

2. Dehydration of Alcohols: Dehydration of

Mechanism of dehydration:
alcohol is a -elimination reaction in which
H2O molecule is removed from adjacent (i) Formation of protonated alcohol
carbon atoms (,  carbon atoms). 
( R  O H2 )
Dehydration of all types of alcohols leads to
olefins.

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Alcohols, Phenols and Ethers 5

(C5H5NHCrO3Cl-Mild oxidising agent. It is
| | H
| |
C  C  CC known as Collin's Reagent. PCC is
fast
| | | | mixture of pyridine, CrO3 and CrO3 and
H OH H  OH 2 HC1 in 1 : 1 : 1 ratio.
protonated alcohol (oxonium ion)
Ease of oxidation of alcohol is 10 > 20 > 30
(ii) Formation of carbonium ion by loss of (a) Primary Alcohols:
water molecule
CH 3  CH 2  CH 2  OH  [O] 
PCC

| | | | 1 propanol

 C  C  H 2 O
slow
C  C 
| | | | CH 3  CH 2  CHO  H 2 O
H  OH 2 H propanal
carbonium ion
K 2 Cr2 O7  dil. H 2SO4
CH 3  CH 2  CHO  [O]  
(iii) Formation of alkene by loss of proton
CH 3  CH 2  COOH
propioniacid

(b) Secondary Alcohols :

In all cases, reaction intermediate is CH 3

| K 2 Cr2 O7  dil. H 2SO 4
carbocation, and in higher alcohols there CH 3  CH  OH  [O]  
2  propanol
may be 1-2 hydride shift or 1-2 methyl shift
to form more stable carbocation.
CH 3
|
CH 3 CH 3  C  O  H 2 O
| acetone
CH 3  C  CH 2  OH 
conc. H 2 SO 4

|
CH 3 CH 3
| K 2 Cr2 O7  dil. H 2SO 4
CH 3  C  O  4[O]  acetic acid

CH 3 CH 3
| |
CH 3  C  C  H  H 2 O CH 3  COOH  CO 2  H 2 O
acetic acid
2 methyl but  2  ene

(c) Tertiary Alcohols :

OXIDATION OF PRIMARY, SECONDARY
AND TERTIARY ALCOHOLS OR CH 3
DISTINCTION OF PRIMARY, SECONDARY | K 2 Cr2 O 7  dil. H 2SO 4
AND TERTIARY ALCOHOLS BY CH 3  C  OH  strong heat

|
OXIDATION REACTION: CH 3
The oxidation can be carried out by various
oxidising agents such as
CH 3
(i) K2Cr2O7 + dil. H2SO4 |
CH 2  C  H 2 O
(ii) KMnO4 + dil. H2SO4 |
CH 3
(iii) Neutral and aqueous KMnO4 iso butylene

(iv) Dil. HNO3

(v) CrO3 Chromium Oxide CH 3
(vi) H2CrO4 Chromic Acid | K 2 Cr2 O7  dil. H 2SO 4
CH 2  C  4 [O] 
drastic oxidation

(vii) Alkaline KMnO4 |
CH 3
(viii) Pyridinium chloro chromate (PCC) or
Pyridinium dichromate (PDC

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CH3–O–CH(CH3)2 methyl isopropyl ether
CH 3
| (ii) Methyl n-propyl ether and methyl iso propyl
CH 3  C  O  H 2 O  CO 2 ether are position isomers.
acetone
CH 3–O–CH 2–CH 2–CH 3
CH 3 CH 3–O–CH(CH 3) 2
| K 2 Cr2 O7  dil. H 2SO 4
CH 3  C  O  4 [O] 
drastic oxidation
 Note: Metamers are either chain or position
isomers. If metamerism is mentioned never
CH 3  COOH  CO 2  H 2 O write chain or position isomerism.
acetic acid
PREPARATION METHODS
Actually, formic acid is obtained along with 1. Williamson's Synthesis : When alkyl
acetic acid but it readily undergoes further halides are heated with alcoholic sodium
oxidation gives CO2 and water. alkoxide to give ethers. This is the laboratory
method used for preparation of simple and
SECTION-II : ETHERS mixed aliphatic and aromatic ethers. But this
method is conveniently used to prepare
INTRODUCTION
mixed ether
Ethers are dialkyl derivatives of water obtained

by replacing both hydrogen atoms from water by R  X  R  ONa 
alc.
R  O  R  NaX
alkyl halide sod. alkoxide ether
alkyl groups.
e.g., When methyl chloride is heated with
 2H
H  O  H 
2 R
 R OR ale. sodium methoxide, gives dimethyl ether.
Mechanism: It is SN2 reaction of R–X, in
Ethers are represented as. R—O—R, known as
which –X is replace by RO–
ether linkage. These are represented by general
formula CnH2n+2O. In ethers, central oxygen atom  RO   Na 
Step 1: R  ONa 
is sp3-hybridised state forming two sigma bonds
with two alkyl groups leads to angular V shaped Step 2: R  X  RO 

geometry like water, having bond angle 1100, bond  
angle in water is 104. Thus ethers have bent R  O     R    X 
Fast
 R  O  R  X
T. S.
structure and dipolar in nature.
  Step 3 : Na   X  
 NaX
O

O


H H R 2. From Diazomethane and Alcohol : This

R
Isomerism method is used to prepare simple and mixed
They shows optical, metamerism themselves and ethers.
functional isomerism with monohydric alcohols. When alcohols are reacted with
Metamerism : diazomethane in the presence of fluoroboric
acid HBF4 or BF3 as catalyst to give ethers.
Metamerism is present in same class of
compounds. R  OH  CH 2 N 2 
HBF4
 R  O  CH 3  N 2 
Organic compound having same molecular Note: This is also known methylation of
formula and different structural formula and alcohols. CH2N2 acts as methylating agent.
different alkyl groups (nature and type) attached Ether produced is pure will always have
to either side of oxygen atom. methyl as one of the group. These are
e.g. nucleophilic substitution reactions.
(i) Molecular formula C 4H 10O have three 3. By Continuous Etherification Process
ethers and all are metamers. (Intermolecular Dehydration of
C2 H5–O–C2H5 diethyl ether Alcohols):
CH3–O–CH2–CH2–CH3 methyl n-propyl Step-I : When ethyl alcohol is heated with cone.
ether H2SO4 at 413K, gives ethyl hydrogen sulphate.

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CHEMICAL PROPERTIES
C 2 H 3  OH  H 2SO 4 
413 K

ethanol conc. These are chemically less reactive (inert) towards
most of the base, metals, oxidising agents,
C 2 H 5  OSO3 H  H 2 O
ethyl hydrogen sulphate reducing agents and RMgX. Thus the properties
of ethers are due to alkyl group, lone pair of
Step-II: Ethyl hydrogen sulphate is reacted
electrons on oxygen and breaking of C–O bond.
with another molecule of ethyl alcohol gives
The C–O bond is not so stable as C–C bond.
ethoxy ethane.
The C–O bond is ruptured in the presence of
C2 H5  OSO3 H  C2 H5  OH 
413 K
 number of reagents like cone. HBr or cone. HI
or dil. H 2 SO 4 and undergoes nucleophilic
C 2 H 5  O  C 2 H 5  H 2SO 4 substitution reactions.
ethoxy ethane
Reaction due to breaking of C–O bond :
The H2SO4 produce in second step is used
Reaction with HX : The cleavage of ethers takes
to convert more and more alcohol into ether.
place with concentrated HI or HBr. The reactivity
Hence this method is known as continuous
of HX is HI > HBr > HC1. The reaction takes
etherification process.
place with only cone. HI and HBr because these
Purification : Ether obtained by this method are sufficiently acidic. Reaction does not takes
contains H 2O, alcohol and H 2SO 4. To place with cone. HC1 because it is not sufficiently
remove these impurities it is first shaken with acidic.
NaOH, which neutralise H2SO4 then add
Reaction with cold conc. or dry HI: When
CaCl2 to remove alcohol. Then dried over
ethers are reacted with cold HI to give alcohols
fused CaCl2.
and alkyl iodides.
Mechanism :
(i) Formation of ether is SN2 reaction involving R  O  R  HI 
cold
 R  I  R  OH
ether alkyl iodide alcohol
the attack of proton on alcohol to form
e.g., When methoxy ethane is reacted with cold
protonated alcohol
HI to give methyl iodide and ethyl alcohol.
H
| C 2 H 5  O  CH 3  HI 
cold
 CH 3  I  C 2 H5  OH
 
CH 3 CH 2  O

 H  H  CH 3  CH 2  O  H methoxy ethane methyl iodide ethanol

–
protonated alcohol Note : The nucleophile I attacks –CH3 group
and not –CH2 group of ethyl group, because the
(ii) Attack of protonated alcohol on another
positive charge on – CH2 is reduced by electron
alcohol to form oxocation.
donating effect on –CH 3 in ethyl group.
Consequently, positive charge on –CH3 is more
than on –CH2 of ethyl group.
Mechanism:
Step I: The reaction of ethyl methyl ether with

cone HI starts with protonation of ether molecule
CH 3  CH 2  O  CH 2  CH 3  H 2 O
| to form oxonium ion.
H
H
(iii) Loss of proton from oxocation to form ether |
CH 3O  C 2 H 5  H  I CH3  O  C 2 H 5  I 

 oxonium ion
CH 3  CH 2  O  CH 2  CH 3
|
H Step II: Iodide is good nucleophile, it attack on
least substituted carbon of oxonium ion and
 displace ethanol SN2 mechanism.
 
Fast
 CH3  CH 2  O CH 2 CH 3  H 

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Aromatic ethers :
e.g.
(i) When anisole is reacted with cold HI to give
phenol and iodo methane.
C6 H5  O CH3  H
anisole
Branched Ethers:

cold
 C6 H5  OH  CH3  I
If mixed branched ethers containing one the alkyl
group is tertiary then halide formed is tertiary. In case of anisole methyl phenyl oxonium
ion is formed by protonation
(i) C 2 H 5  O  CH(CH 3 ) 2  HI
2  ethoxy propane 
C6 H 5 O CH 3

 C 2 H 5  I  (CH 3 )2 CH  OH
cold
weak bond
ethyl iodide iso propyl alcohol
H
strong bond
(ii) CH 3  O  C(CH 3 )3  HI
t  butyl methyl ether The bond in CH 3 –O is weaker than
C6H5–O because carbon of phenyl group is

cold
 CH 3  OH  (CH 3 )3 C  I sp2 hybridised state and there is a partial
methanol and butyl iodide
double bond character. Therefore attack of
Mechanism of t-butyl Methyl Ether: I ion breaks CH 3 – O bond to form
It is three step reaction follows SN1 mechanism CH3—I, and C6H5–O– combine with H+ to
and formation of (CH3)3 C+ carbonation. form C6H5–OH.
Step I : Protonation of ether to form oxonium ion
(ii) CH 2  O   HI 
Cold

CH 3
|  benzyl phenyl ether
CH 3  C  O  CH 3  HI
| 
CH 3 OH  CH 2  I

phenol benzyl iodide

CH3 H
| | II Reaction with hot cone, or dry (excess)
CH 3  C  O H  (CH 3 )3 C  I HI
| 
CH 3 
R  O  R  HI   2R  I  H 2 O
Step II: Dissociation of C–O bond and formation Note: Both alkyl group produces alkyl
of stable t-butyl carbonium ion by SN1 reaction. iodide.
H III Acid hydrolysis (Reaction with dil.
| H2SO4) :
 (CH3 )3 C  CH 3  OH
(CH 3 )3 C  O  CH 3 
 t  butyl carbonium ion
When ethers are hydrolysed by dilute H2SO4
Step III: Attack of nucleophile (I ) on t-butyl – under pressure to give alcohols.
carbonium ion. dil. H 2 SO 4 
R  O  R  H 2 O   R  OH  R  OH
ether under press alcohol
 
(CH 3 )3 C  I 
 (CH 3 )3 C  I Note: Both alkyl group produces alcohols.
t  butyl iodide
ELECTROPHILIC SUBSTITUTION
Note: This reaction is useful for detection of alkyl REACTION OF AROMATIC ETHERS
group in mixed ether.
The alkoxy group attached to benzene ring is ortho
and para directing like phenol

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1. Halogenation : Alkyl phenyl ether reacts e.g..
with bromine in acetic acid in the absence OR O  CH3 O  CH 3
of FeCl3 or FeBr3 catalyst to give ortho | | |
bromo alkyl phenyl (10%) and parabromo CH 3
 CH 3  Cl 
Anhydrous
   HCl
alkyl phenyl ether (90%). AlCl .CiS
3 2

OR OR OR anisole 2  methoxy |

toluene
| | | (min or) CH 3
Br 4  methyl
toluene
 Br2 
CH 3COOH   HBr (major)

Minor | (b) Friedel-Craft acylation: Acylation can be

Br
Major carried out by acylating agents like RCOC1,
e.g.
(RCO)2 O,R–COOH
O  CH 3 O  CH 3 O  CH 3 OR OR OR
| | | | | |
Br COR
 Br2 
CH 3COOH
   HBr  R  COCl 
Anhydrous

AlCl3  H 2O
10%
o  bromoanisole 2  alkoxyl |
(min or) Br alkyl phenyl COR
90 % ketone 4  alkoxy
p  bromo (min or)
alkyl phenyl
anisole (major) ketone (major)
e.g.
2. Nitration: Alkyl phenyl ether reacts with
nitrating mixture (conc. HNO3 + conc. O  CH3 O  CH 3 O  CH 3
H2SO4) to give a mixture of o-nitro alkyl | | |
COCH 3
phenyl ether (minor) and p-nitro alkyl phenyl  CH3COCl   
Anhydrous
AlCl3  HCl
ether (major).
OR OR OR
2  methoxy |
| | |
acetophenone
(min or) CO  CH 3
NO 2 4  methoxy
acetophenone
 HNO 3 
 conc. H 2SO 4   H2O CROWN ETHERS (major)
conc.
Charles J. Pederson discovered crown ether. It
(major)
e.g. NO 2 is macrocyclic polyether containing large ring of
10 % (major ) carbon and oxygen atoms. Crown ethers are
O  CH 3 O  CH 3 OR named as n-crown-m. Where 'n' is the total
| | | carbon and oxygen atoms and 'm' is total oxygen
NO 2
 HNO3 
conc. H 2SO 4
  H2O atoms.
conc
anisole 2  nitroanisole
(min or)
NO 2
4  nitro anisole
(major)
3. Friedel-Craft reactions:
(a) Friedel-Craft alkylation: In this reaction alkyl
groups is attached to ortho and para position.
OR OR OR
| | |
R
 (a) The cavity inside is able to trap K+ but not
 R  X 
Anhydrous
  H2O
AlCl3 , CS2
Na+ and Li+
2  alkoxy | (b) The another crown ether is 15-crown-5
alkyl benzene R
(mior)
4  alkoxy ether, it is able to trap Na+ ions.
alkyl benzene
(major)

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2. From chlorobenzene by Dow's method
(1928) Industrial method :
Cl ONa
| |

 2NaOH 623 K
300 atm. press
  NaCl  H 2 O

Chlorobenzene Sodium phenate

ONa OH
| |
In crown ether each oxygen atom is co-
ordinatly bonded with sodium atom.  HCl dil. 
  NaCl
+
(c) Crown ether also form complex with NH4
Sodium phenoxide Phenol
and R–NH3
(d) Stability of these complexes depends upon
size of the metal ion and cavity available in 3. From benzene sulphonic acid:
the ring of particular crown ether.
SO3 H SO3 Na
(e) Application: | |
(i) It is used for increasing solubility of ionic
 NaOH 
Neutralization
  H 2O
salt in non-polar solvent
(ii) They also act as catalyst in certain reactions Benzene sulphonic acid Sod. benzene sulphonate
involving organic salt. SO3 Na ONa
(iii) They are used to extract specific ion from | |
mixtures and enrich isotopic mixtures. 2NaOH 
573 K

fused  NaSO 3  H 2 O
(iv) It is used to remove radiative elements from
radioactive waste. Phenol
(v) Specific crown ether 18-crown-6 is used to ONa OH
| |
extract cesium and strontium.
 H 2SO 4 
 2  Na 2SO 4
SECTION-III : PHENOLS dil.

INTRODUCTION Sodium phenate Phenol

Phenols are aromatic hydroxy compounds in
4. From oxidation of cumene (Isopropyl
which one or more hydroxy groups are directly
benzene or 2-propl benzene or 2-phenyl
attached benzene nucleus.
propane):
Simple phenol is hydroxy benzene or phenyl
hydroxide or benzenol or phenol it self also known CH 3 CH 3
as carbon acid. It is represented as Ar-OH or | |
CH 3  C  H CH 3  C  OOH
Ph-OH where Ar or Ph is C6H5-group. | |
PREPARATION OF PHENOL (CARBOLIC Co. naphthenate

ACID)  O 2 
in Na 2 CO3

403 K

1. From chlorobenzene by Raschig's Cumene (2  propyl Cumene

benzene) hybdroperoxide
method (1943) Industrial method:
CH3
|
Cl OH CH 3  C  COOH OH
| | | |
 H 2 O 
CuCl2
698 K
  HCl 
dil. H 2 SO 4
  CH 3  CO  CH 3


Chlorobenzene |
phenol

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From diazotisation reaction: But this effects is more when substituents
is present on ortho and para position than
NH 2 N   NCl meta position. It follows the order
| |
273 to p > o > m > ph—OH
 HNO 2  HCl 
278 K
  2H 2 O
Greater the number of electron withdrawing
groups at ortho and para position, more the
N 2 Cl OH acidity of phenol. Thus increasing order
| | acidic strength of nitrophenol is p-nitrophenol
H / > o-nitrophenol > m-nitrophenol > phenol.
 H 2 O    N 2  HCl
e.g.
OH OH OH OH
| | | |
ACIDITY OF PHENOLS O2 N NO 2 NO 2
The reaction of phenol with sodium, potassium,   
aluminium metal, NaOH, KOH, indicates the | | |
acidic nature of phenol. It does not react with NO 2 NO 2 NO2
NaHCO3, Na2CO3.
pka value 0.71 4.0 7.15
In phenols – OH group is directly attached to sp2
hybridised carbon atom, this increase the polarity 2. Effect of electron donating groups
of O – H bond and increase the ionisation of (EDG) like R—OH, —OR, —NH 2_,
phenols than alcohols. NR2 etc. on acidity of phenols: Electron
donating groups destabilize the phenoxide ion
C6 H 5 OH  H 2 O C6 H 5 O   H 3O 
phenoxideion by donating electron to benzene ring and
decrease the acidic strength of phenol.
Phenoxide ion is more stabilized than phenol by
Acidic nature is more when electron
resonance. Hence phenol is acidic in nature.
donating group is present on meta position.
OH O
| |
 H

D D
 H 2 O D  destabilize the anion

Thus cresols are less acidic than phenols.

EFFECT OF SUBSTITUENTS ON ACIDITY The decreasing order of acidic strength of
OF PHENOLS cresols is,
The presence of electron attracting and electron
donating groups affects the acidic strength of phenols. OH OH OH OH
| | | |
1. Effect of electron withdrawing group CH 3
(EWG) like — NO2, —CHO, —COOH,   
—CN etc. on acidity of phenols:
CH 3 |
Electron withdrawing group or atoms CH 3
stabilize the phenoxide ion and increase the phenol m-cresol o-cresol p-cresol
acidic strength of phenols. 10 10.1 10.14 10.2
OH O
| |
Note: Lower the pKa value stronger the
 H
acid, or higher the Ka value stronger the
acid. The pKa value of ethaiiol is 15.9 hence
W W
Acidic strength more W  stabilize the anion it very less acidic than phenol.

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Compounds pKa value OH OH

| |
Ethanol 15.9 Br
p-amino phenol 10.5  Br2 gas  CS2
273 K cold

p-cresol 10.2 Phenol O  bromophenol (20 %)

o-cresol 10.14 OH
|
m-cresol 10.1
Phenol 10.0   HBr
p-chloro phenol 9.4 |
m-chloro phenol 9.1 Br
P  bromophenol (80 %)
o-chloro phenol 8.6
(b) Reaction with bromine water:
m-nitro phenol 8.3
OH OH
o-nitro phenol 7.2 | |
p-nitro phenol 7.1 Br Br
 3Br2 
Water
  3HBr
Following groups increases the acidity of
phenol in decreasing order. Phenol |
Br
–SO3H > – COOH > –NO2 > F > Cl > 2, 4, 6 tri bromo phenol
Br > I >–OH > – OCH3 > – CH2
2. Nitration at different condition:
CHEMICAL PROPERTIES
(a) Reaction with dil. HNO3:
Phenol undergoes two types of reactions by
breaking of O–H bond and by breaking of C–O OH OH
| |
bond. Hence reactions are divided in to two
NO 2
groups.  HNO3 dil. 
R.T.

300 K
1. Reaction involving breaking of –OH
bond (acidity of phenol) Phenol 2  nitrophenol (40 %)
(i) Reaction with Na metal OH
|
OH ONa
| |   H2O
2  2Na 
  H2 |
NO 2
4  nitrophenol (13 %)
(ii) Reaction with NaOH OH
(b) Reaction with cone, nitric acid (nitrating
mixture):
OH ONa
| | HNO3 + 2H2SO4  2HSO4– + H3O+ + NO2+
OH
2  2NaOH 
  H 2O |

3 HNO3 
conc. H 2SO 4


conc.
Phenol
ELECTROPHILIC SUBSTITUTION OH
REACTION OFPHENOL |
O2 N NO 2  3H 2 O
(Reaction involving breaking of C–O bond)
1. Bromination in different solvent:
(a) Reaction with Br2 gas in inert solvent |
NO2
non polar solvent (CS2, CHC13, CCl4):
2, 4, 6, trinitro phenol

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3. Sulphonation at different temperature: 5. Reimer and Tiemann reaction:
a) Reaction with conc. H2SO4, at R.T./300 K : OH
OH |
OH
| |
SO 3 H  CHCl3  3NaOH (aq)
 H 2SO 4 
 R.T.
 3H 2 O
conc.
300 K OH
|
Phenol ortho phenol CHO
sulphonic acid

333 K
  3NaCl  2H 2 O
(b) Reaction with conc. H 2 SO 4 at high
temperature (373 K): 6. Reaction with Zn metal :
OH OH
| | OH
|
 H 2SO 4 
373 K
  H2O
conc.
 Zn 
  ZnO
Phenol |
SO3 H Phenol
para phenol
sulphuric acid 7. Oxidation of Phenol: When exposed to
air or heating with strong oxidising
4. Kolbe's Schmidt reaction: agent like K 2 Cr 2 O 7 + dil. H 2 SO 4 it
undergoes slow oxidation and turn pink
to from phenoquinone or p-benzoquinone
OH ONa
| | or conjugated diketone

 H2O OH O
 NaOH 
 | ||
sodium phenoxide  O 2 
air
  H2O
ONa OH
| |
COOH  NaCl
 CO2 
 HCl
8. Colour Test of Phenols : In fact all
compound containing enolic group
salicyclic acid
|
(C  C  OH) gives FeCl3 test, forming
chelate compound. Phenol gives ferric
phenoxide as chelate compound.
 [Fe(C6 H 6 O)6 ]3
6C6 H5OH  FeCl3 
+ 3H+ + 3HCl

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Alcohols, Phenols and Ethers 1

MULTIPLE CHOICE QUESTIONS

Section I : Alcohols 8. Grain spirit is
Introduction, Nomenclature, Classification a) isopropyl alcohol b) isobutyl alcohol
Isomerism c) methyl alcohol d) ethyl alcohol
1. IUPAC name of following compound is 9. Which of the following has primary alcoholic
group?
OH
OH a) b)
OH
a) pent-3-en-2-o1
b) pent 2-en-4-o1 OH
c) but-3-en-2-o1 c) d) OH
d) but-2-en-4-o1
2. How many isomers of C5H11 OH will be 10 10. The characteristic grouping ofs condaryalcohol
alcohols?
a) > C=O b) – CH2OH
a) Five b) Four
c) > HOH d) –7COH
c) Two d) Seven
11. Which of the following alcohol cotain vinyl group
3. Which of the following is trihydric alcohol?
OH OH
a) Glycine b) Glycerol a) b)
c) Glycol d) 2-heptanol
4. In glycerine, OH
OH
a) one 10 OH group is present c) d)
b) one 2° OH group is present
12. How many ethers are possible for formulae
c) two 2° OH group are present
C 4H 10
d) one 3° OH group is present
a) 2 b) 3
5. Correct IUPAC name of the following compound
c) 4 d) 5
is
13. In allylic alcohol-OH group is ttached to
a) 3-phenyl butan-3-o1
a) s - hybridised carbon atom
b) 2-phenyl propan-2-ol
b) sp2 – hybridised carbon ato
c) 2-phenyl butan-2-o1
c) sp3 – hybridised carbon ator
d) 3-phenyl butan-2-o1
d) sp3d– hybridised carbon at m
6. General representation of primary alcohol is
14. Which of the following is allylic alcohol
OH
OH OH
a) b)
Ph
OH
a) > C = O b) –CH2OH OH
c) d)
c) > CHOH d) :::COH
7. The general formula, which represent the 15. Butane-2-01 is
homologous series of alcohol is a) primary alcohol b) secondary alcohol
a) CnH2nO b) CnH2n+1O c) trtiary alcohol d) aldehyde
c) CnH 2nO 2 d) CnH2n+2O

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16. Allylic alcohols may be 25. Ethyl methyl carbinol is
a) 1 types b) 2° types a) n-butyl alcohol
c) 3 types d) 1°,2°,3° t pes b) t-butyl alcohol
17. Whic is a primary alcohol? c) sec.butyl alcohol
a) Butan-2-ol b) Butan-l-o d) isobutyl alcohol
c) Propan-2-ol d) Isopropyl lcohol 26. Following alcohol is the type of
18. Aralkyl alcohols are also name as
a) allylic alcohol b) vinylic alcohol
c) benzylic alcohol d) aryl alcohol a) allylic alcohol b) vinylic alcohol
19. IUPAC name of the compound c) aralkyl alcohol d) benzylic alcohol
CH3CH(C2H5) CH2CH(OH)CH3 is 27. Methyl carbinol is
a) 2-metyl 3-hexanol b) 4-metyl 2-hexanol a) ethanol b) 2-propanol
c) haptanol d) all of these c) I-propanol d) methanol
20. Following alcohol can be named as 28. Vinyl carbinol is
a) HO–CH2 – CH = CH2
b) CH 3  C  CH 2
|
OH OH
a) l-phenyl 1-methyl propan-2-ol c) CH3–CH=CH–OH
b) 3-phenyl butan-2-ol 29. group is present in
c) 1-methyl 1-phenyl butan-2-ol a) 10R – OH b) 20 R–OH
d) 3-phenyl 3-methyl propan-2-ol c) 30 R – OH d) 40R–OH
21. Wood alcohol is 30. Ethanol containing some metha
a) phenol b) CH3OH a) methylated spirit b) rectified spirit
c) C2H5OH d) CH3COOH c) absolute spirit d) proof spirit
22. In venyl alcohol-OH group is attached to 31. IUPA name of secondary butyl
a) sp - hybridised carbon atom a) 2- methyl propan-l-ol
b) Sp2– hybridised carbon atom b) butan-2-ol
c) Sp3– hybridised carbon atom c) 2- ethyl propan-2-oJ
d) Sp2– d-hybridised carbon atom d) 1- utanol
23. How many metamers are possible for C4H10O? 32. IUPA name of the following compound is
a) 1 b) 2
c) 3 d) 4
24. IUPAC name ofthe following compound is
OH
CH–OH
a) cyclohexa 1-3-dien-3-0l
CH b) cyclohexa 1, 2-dien-l-ol
c) cyclohexa 1, 3-dien-3-ol
a) 1-methyl 1-phenyl methanol
d) cyclohexa 1, 5-dien-l-01
b) 2-methyl benzyl alcohol
c) 2-phenyl ethan-2-ol
d) l-phenyl ethan-1-ol

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Alcohols, Phenols and Ethers 3

33. IUPAC name of following compoound is 39. Molecular formula C2H60 represents
a) alcohols and acids
CH 3
| b) alcohols and ethers
CH 3  CH 2  CH  CH 2  CH 2 OH c) only alcohols
d) only ethers
a) 5-ethyl 3-methyl pent-l-ol
40. Which isomer of C4H10O is optically active?
b) 3-methyl pent-l-ol
c) 3-ethyl pent-l-ol OH
a) b) OH
d) 3,5-diethyl pent1-ol
34. IUPAC name of following compound is
c) d) OH
OH OH
41. Molecular formula C3H8O shows
a) chain and optical isomers
b) position and functional isomers
a) cyclobutyl benzenol
c) functional and metamers
b) 2-cyclobutynol benzene
d) chain and position isomers
c) 2- phenyl cyclobutan-1-ol
42. IUPAC name of following compound is
d) 3- phenyl cyclobutan-I-ol
OH
35. IUPAC name oft-butyl alochol is
a) 2-methyl propan-l-ol a) pent-2-yn-5-ol
b) 2-methyl butan-l-ol b) pent-3-yn-l-ol
c) 2-methyl propan-z-ol c) pentane-2-yn-5-ol
d) L-methyl propan-2-ol d) pentane-3-yn-l-ol
36. IUPAC name of following compound is 43. Alcohols exhibit
a) chai isomerism
OH
b) position isomerism
c) optical isomerism
d) all of these
44. Total n mber of isomers including structural and
a) 2, 5-dimethyl phenol stereoisomers of molecular formula C4H100
b) 3-5-dimethyl phenol a) 4 b) 7
c) para-dimethyl phenol c) 8 d) 10
d) dimethylene phenol 45. What type of isomerism is exhibite by pentanol?
37. The compound which is not isomeric with diethyl a) Position b) Chain
ether is
c) Opt cal d) All of these
a) n-propy 1methyl ether
46. Number of isomeric ethers with molecular formul
b) butan-l-ol C5H12O are
c) 2-methylpropan-2-ol a) 4 b) 6
d) butanone c) 8 d) 10
38. How many compounds show optical isomerism 47. C4H10 O represents
or molecular formula C5H12O?
a) aldehydes b) ketones
a) 2 b) 3
c) alcohols d) acids
c) 4 d) 5

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Alcohols, Phenols and Ethers 4

48. Which of the following are functio al isomers? 55. Hydroboration oxidation of alkene give
a) Alcohols and ethers a) acids b) aldehydes
c) ketones d) alcohols
b) Alcohols and acids
56. In hydration of alkene first step is
c) Alcohols and aldehydes a) nucleophilic attack of water on carbocation
d) Alcohols and ketones b) deprotonation of carbocation
49. How many 30 alcohols are possible for C3H5O? c) protonation of alkene
a) 1 0 b) 1 d) attack ofH30+
57. In the following reaction most stable intermediate
c) 2 d) 3
is
50. Hydrati n of alkene produces
a) 10 alcohols or 2° alcohols CH 3
b) 10 alcohols or 3° alcohols |
H
c) 10 , 20 and 3° alcohols CH 3CHCH  CH 2 H 2O 
d) 1° or 3° alcohols
51. Hydration CH 3
a) takes place through carbocation |

b) is a reversible process a) CH 3CHCH 2 CH 2
c) follows electrophilic addition
d) fellows all of the above CH 3
52. Hydra ion of following compound gives |
b) CH 3CH CH CH 3


CH 3
OH |
c) CH 3 CCH 2CH 3

a) b)
OH
CH 3
|
d)
c) d) CH 3CHCH 2 C H 3
OH OH
53. Which is hydrated to a maximum extent? 58. In the hydration of an alkene carbocation is formed
from
CH 3 a) carbanion b) oxonium ion
| c) hydroxide ion d) hydride ion
a) CH 3  C  CH  CH 2
59. Reaction intermediate in hydration of alkene is
| a) carbanion
CH 3 b) carbon free radicals
b) CH3–CH = CH2 c) carbocation
c) CH2 = CH2 d) carbene
d) CH = CH A
54. Which reagent can bring about following 60. OH O   O
conversion
In above reaction A and B respecti ely
OH
a) H2/Pt, LiAlH/H2O
b) H2/Pt, H2/Pt
a) CrO3 b) acidic KMnO4 c) LiAlH4 /H2O, LiAlH4 / H2O
c) dil. H2SO4 d) dil. KOH d) LiAH4/H2O, H2Pt

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Alcohols, Phenols and Ethers 5

61. In hydr boration oxidation of alkene, the initial
attack c) CH 3CHCH  CH 2
|
a) baron b) NaOH CH 3
c) H2O2 d) H+
62. Select is correct statement about hydroboration
oxidation: d) CH2

a) Addition is against Markownikoff rule

67. Find out (B) in the following reaction
b) Interediate is a carbocation
C3H8 + Br2  AlBr3
 (A) 
Aq.KOH
 (B)
c) It does not involve rearrangement
d) It is addition reaction a) CH3–CH = CH2
b) CH3–CH2–CH2–OH
63. Reagents used in hydroboration oxidation reaction
c) CH3–CHOH–CH3
a) B2H6 + CrO3+ NaOH
d) CH3–O–C2H5
b) B2H6 + H2O + NaOH, THF
68. Which of the following reactions will yield
c) B2H6 + acidic KMnO4 + NaOH
H
1) CH2 =CH–CH3 + H2O 
d) B2H6 + dil.HNO3 + NaOH
CH 3Mgl
64. A changes to with hydroboration-oxidation (2) CH3CHO 
H 3O 


CH 3 CH 3Mgl
(3) HCHO  
H 3O 
|
A: CH 3CH  CCH CH 3Mgl
(4) CH3COCH3  
H 3O 

a) 1 and 2 b) 2 and 3
a) CH 3CHCHCH 3
| | c) 3 and 1 d) 2 and 4
OHCH 3 69. Treatment of I-butene with cone.H2SO4 followed
by treatment with water forms
CH 3 a) 1 butanol b) 2 butanol
b) | c) 2-propanol d) 1-2-propan-diol
CH 3CH 2CCH 3 70. Acetone is treated with sodium amalgam and water
gives,
c) CH 3CH 2CHCH 2OH a) (CH3)2CHOH b) CH3CH2CH2OH
| c) C2H5OH d) CH3CH2COOH
CH 3
71. 2-methyl 2-pentanol is prepared from acetone and
d) None of these what?
65. Alcohol containing least number of carbon which a) C2H5Mgl
can be repared using Grignard reagent is: b) (CH3)3CMgl
a) (CH3)2CHOH c) 2-molecules ofCH3MgI
b) (CH)3COH d) CH3CH2CHgl
c) CH3OH 72. The only primary alcohol that can be prepared by
the indirect hydration of alkene is
d) CH3CH2OH
a) ethyl alcohol b) n-propyl alcohol
66. Following alkene will give same product by any
c) isobutyl alcohol d) methyl alcohol
method out of hydration, hydroboration oxidations:
73. R2CO  R2CHOH.The convers on is.
a) CH3CH = CH2
a) reduction b) oxiidation
b) CH3CH = CHCH3
b) hydrorolysis d) hydration

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Alcohols, Phenols and Ethers 6

74. Proper can be converted into' -Propanol by
OH
hydration. Which of the following reagents is ideal
affect the conversion?
a) Al aline KMnO4 b) Zn dust + H2O c) d)
OH
c) Conc. H2SO4 d) Conc. HCI
75. Using H3MgBr, which substrat would lead to 82. Which of the following is best reducing agent to
(CH3)3 OH? convert –COOH to –CH2–OH
a) Acetone b) Acetyl chloride a) Fe + cone.HCI b) LiAlH4
c) Acetaldehyde d) Isopropyl alcohol
c) NaBH4 d) Zn.Hg + HCI
76. Which the following is IUPAC name fthe
83. Methanol is obtained by reduction of
compound formed from reduction of 2-butanone?
a) 1-butanol b) 2-butanol a) CH–CHO b) CH3–COOH
c) l-butanal d) 2-butanal c) H–CONH2 d) H–COOH
77. Alcohols can be prepared by hydration of, 84. Product of the following reaction will be
a) alkenes b) alkyl halides
O
c) alkyl amines d) alkenes
78. CH3 CH2–CH2–CO–CH2–CH CH3)2
Catalytic hydrogenation of above compound in OH 
LIALH 4
 ?
the presence of nickel catalyst gives
a) an optically inactive compoun CH2–OH
b) an opticallyactive compound
c) compound with plane of sym a) b) OH
d) a tertiary alcohol
79. Alken s convert into alcohols by COOH
a) hydrolysis by dill.H2SO4
b) hydration of alkene by conc.804 c) d) OH
c) hydrolysis by water vapours and conc. H2SO4
d) hydration of alkeneby aqueo s KOH 85. Ethanol is obtained by in which of the following
80. Acid atalysed hydration of a kenes except ethene reaction
leads to the formation of (i) conc, H 2SO 4
1.  
a) seccondary or tertiary alcohol (ii) H 2SO 4

b) primary alcohol O
c) mixture of secondary and telrtiary alcohols dry ether
2. + CH3 – MgX 
H 3O

d) mixture of primary and seeondary alcohols
H
81. Following compound on reduction gives
O

dry ether
3. + CH3–MgX 
H 3O

O
H H

OH O

LiALH 4
4.  
a) OH b)
OH
OH
a) 1,3 b) 1,2,4
c) 3,4 d) 1,3,4

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Alcohols, Phenols and Ethers 7

86. Which of the following is best reagent followinng
OH
conversion?
O c) d)
? O O
 
OH
H 92. Isobutyl alcohol can not be obtained by the
a) H2/Ni b) H3O + reaction between
c) NaBH4 d) Zn.Hg+HCl H
87. Which one of the following will yields propan-2-
MgX dry ether
choose the right answer from a to d? 1. + 
H O

2

a) H 2O / H 

 O

H O
(i ) CH 2 MgX dry ether
b) 
(ii) H O / H 
 2. + CH3–MgX  
2 H 2O
O H
(i) C2 H 6 MgX
c) CH2O 
(ii ) H 3O 

H H
Neutral
d) KMnO 4 dry ether
3. + 
H O

3
88. When C2H5MgI react with ace one and the addition MgX
O
products is hydrolysed we get
a) 10 alcohol b) 2° alcohol
dry ether
c) 3° alcohol d) an aldehy e 4. + CH3 – MgX 
H 3O 

89. Identify (Z) in the following serie of reaction. O
a. 1, 2, 3 b) 1, 2, 4
(i) H 2SO 4 RT
PCl5
  (X) 
KOH
 (Y)
 (Z) (ii) H 2 O
c) 1, 3, 4 d) 2, 3, 4
OH 93. Which set of following reagent would you se ect
to convert C6H5COCH5 to following alcohol

a) b) OH Ph
OH
OH OH
c) d) OH

90. Benzy alcohol is obtained by reduction of a) CH3–CH2–H2 MgBr and hydrolysis

a) be zoic acid b) acetophe one b) CH3– CH –CH3, AlCl3

c) be zonitrile d) benzamid |
Br
91. To pre are butan-2-ol from meth I magnesium
iodide. The compound required is a) 1, 2, 3, b) 1, 2, 4
c) 1, 3, 4 d) 2, 3, 4
H
O 94. Propan-Ivol may be prepared by the reaction of
propene with
a) b)
H a) H3BO3
O

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Alcohols, Phenols and Ethers 8

0 0
b) H2SO4RT/H2O c) 1 or 2 alcohols
c) B2H6/ THF, H2O2 and NaOH d) 20 or 30 alcohols
d) (CH3COO)2Hg/NaBH4 100. Benzaldehyde and phenyl mag esium halide gives
95. Styrene on hydroboration oxidation gives a) Benzyl alcohol
a) 2-phenyl ethan-Lol b) I-phenyl ethan-l-ol b) diphenyl ketone
c) benzoic acid d) benzaldehyde c) diphenyl ethanol
96. Which of the following produces only one product d) diphenyl methanol
on reduction with LiAlH4 101. Whicg reagent can
a) CH3COOC2H5 R–COOH R– CH2 – OH
b) C2H5COOC2H5 a) Sn+HCl b) Na+C2H5OH
c) C2H5COOCHa c) H2+Pt d) LiAlH4
d) CH3COOCH2CH2CHa 102. When wine is put in air, it become sour due to
97. Catalytic hydrogenation of methyl 2-methyl a) reduction of C2H5–OH
propanoate gives
b) reduction of C2H5–OH
c) formation of C2H5–OH
a) and CH3OH d) dissolution of CO2
OH 103. Reactio used to convert acid to 1° alcohol is
a) oxidation b) reduction
b) and CH3OH c) polymerisation d) pyrolysis
OH
104. Carb xylic acid on reduction produces
a) 10 alcohols b) 20 alcohols
OH
c) and c) aldehydes d) ketones
OH 105. Prodoct of the following reaction
OH O
d) and MgX
OH
dry ether
+ 
H O

3
O H

98. CH 3  CH  C  O  CH 3 on reduction gives a) ethhyl alcohol b) l-pheny ethanol

c) phenyl methanol d) methyl henyl ketone
106. Ethene is subjected to hydroboration oxidation
reaction followed by treatment with PC gives
a) ethyl alcohol b) acetaldehyde
a) 1-phenyl propan-1-ol and methanol c) acetic acid d) acetone
b) 2-phenyl propan-l-ol and ethanol 107. Product of the following reaction
c) 2-phenyl propan-l-ol and methanol
d) 2-phenyl propan-2-ol and methanol HBO reaction
 
d) 2° or 3° alcohols
99. Aldehydes and ketone reacts with Grignards
reagent gives a) OH b) OH
a) mixture of 10, 2, 30 alcohols
OH
b) 10 or 20 or 30 alcohols c) d)

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108. CH2OH group is obtained by reduction of
a) R–CN b) R–NO2
a) b)
c) R–CO–R d) R–COOH OH OH
109. Cyclohexane carbaldehyde is reacted with ethyl
magnesium halide in the presence of dry ether O
OH
and product on acid hydrolysis gives c) d)

OH 113. Acrolin on reduction by using H2/Ni gives

OH
a) b)
a) b)
OH OH
OH
c)
OH d)
c) d) OH
OH 114. Following compound is reduced by NaBH4 or
LiAlH4 gives
110. Product of the following reaction is

O H

MgX dry ether

+ 
H O
 a) OH b)
3 OH

c) d) OH
OH OH
115. 2, 2-d methyl propan-l-ol is obta ned from 2, 2-
a) b) OH dimethyl but-l-ene by using
a) dil. H2SO4
b) B2 6' H2O2 and NaOH
OH c) (CH3COO)2 Hg + NaBH4
OH
d) H2/Ni
c) d) 116. Benzaldehyde on reduction by usi gNaHg
+ H2O gives
111. Hydroboration oxidation of 3-methyl but-l-ene a) benzyl alcohol b) phenol
gives c) sodium benzoate d) sodium p. enoxide
a) 3-methyl butan-2-ol 117. Product of the following reaction is
b) 2-methyl butan-2-ol
c) 3-methyl butan-l-ol B2 H 2 / THF
 
H 2 O 2  OH
d) 2-methyl butan-l-ol
112. Product of the following reaction:
O a) b)
H 2 Ni OH OH



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123. Ethyl formate on catalytic hydrogenation gives
OH
a) CH3–OH b) CH3OH and C2H5OH
c) C2H5–OH d) H-CHO and CH3-OH
c) d)
OH 124. Mixture ofmethanol and ethanol is obtained from
catalytic hydrogenation
118. In which of the following reaction carbocation is
O
not formed O
a) b)
O
B2 H 2 / THF
a)  ? b)
dil. H 2SO 4 
H 2 O 2  OH

O
O
c) d)
Cl
125. 3-methyl but-l-ene on HBO reaction gives
c)  HX d) ?
aq.KOH
a) 3-methyl butan-2-ol
b) 2-methyl butan-2-o1
c) 3-methyl butan-Lol
119. Product of the following reaction carbocation is
not formed? d) 2-methyl butan-Lol
126. HBO of but-2-ene produces
O
a) butan-l-ol
LiAlH 4
 ? b) butan-2-ol
Ether
OH c) 2-methyl propan-2-ol
d) 2-methyl propan-l-ol
OH
127. Reduction of aldehydes and ketones produces
a) b) OH
a) 1° alcohols b) 2° alcohols
c) 3° alcohols d) 1° or 2° alcohols
O
128. Hydroboration oxidation of propene produces
c) d)
H
a) b)
OH
120. Alcohols are obtained by reduction of OH
a) R-CHO b) R-COR
c) R-COOH d) RCOOR OH
c) d)
a) 1, 3 b) 1,3 OH
c) 3, 4 d) 1, 2, 3, 4 129. Molar concentration of alk ne used up in hyd
121. Ester on reduction by using LiAIH4 produces. oboration oxidation reacti n to form alcohol is
a) single aldehyde b) single alcohol a) 2 b) 4
c) mixture of aldehyde d) mixture of alcohol c) 3 d) 5
122. Ester are converted in to mixture of alcohol by 130. Consider the following species
a) acid hydrolysis 1. CH+CH3
b) alkaline hydrolysis 2. RCH2C2+
c) catalytic hydrogenation 3. CH2CH2O + H2
d) oxidation In the dehydration of straight hain 10 alcohols,
the correct sequence of format on of the species
involved is

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a) 2,1 b) 1, 2 137. The main product of the reaction of
c) 3,2 d) 2, 3 (C2H5)2CHCHOHCH3 with cone, H2SO4 is
131. Which of the following reduci g agent is used for a) (CH3CH2)2CH–CH = CH2
following conversion? b) CH3–CH(C2H5)CH–CH–CH3
c) (C2H5)2C = CH–CH3
H
H d) both 'a' and 'b'
?
  138. Place the following alcohols in decreasing ('I ;,-
O of rate of dehydration with cone.H2SO4,
a) H2+Ni b) LiAlH4 (1) CH3CH2CH–CH2CH2CH2
c) NaBH4 d) Na.Hg + H2O (2) (CHl)2C(OH)CH2CH2CH3
132. The correct order of increasin boiling points is (3) CH3CH2CH2CH2CH2CH2–OH
a) n-butane < 1-butanol < n-butyl chloride < (4) (CH3)2C(OH)CH(CH3)2
isobutane a) 4 > 2 > 1 > 3 b) 1 > 2 > 3 > 4
b) n-butane < isobutane < n-butyl chloride < 1- c) 4 > 3 > 2 > I d) 4 > 3 > I > 2
butanol 139. An alcohol C4H9OH on dehydration gives an
c) isobutane < n-butyl chloride < n-butane < alkene, which on oxidation yield a acetone.
isobutane The alcohols is
d) isobutane < n-butane < n-butyl chloride < 1- a) (CH3);POH
butanol. b) CH3CH2CH2(OH)CH3
133. List the class of alcohols in de reasing order of c) CH3CH2CH2CH:PH
reactivity towards HX d) (CH3)2CHCH2OH.
a) 30 > 10 > 2° > MeOH 140. The most stable carbonium ion is
b) 3 0 > 20 > 10 > MeOH a) methyl carbonium ion
c) MeOH > 10 > 20 > 30 b) primary carbonium ion
d) 20 > 30 > 10 > MeOH c) secondary carbonium ion
134. List the hydrogen halide acids i decreasing order d) tertiary carbonium ion.
of reactivity in the following reaction
141. The compound with highest boiling point is
R–OH + HX  RX+H2O
a) CH4 b) CH3CH
a) Br > HI > lICl > HF
c) CH3Cl d) CH:lBr
b) HI > HBr > HCl > HF
142. Hydrogen bonding is maximum in
c) HI > HF > HBr > HCl
a) ethanol b) diethyl ether
d) I > HCl > HBr > HF
c) ethyl chloride d) triethylamine
135. Which one of following is more re ctive than the
143. I-butanol is treated with PCC gives,
rest towards a Lucas reagent?
a) CH3CH2CH2COOH
a) 1-butanol b) 2-butanol
b) CH3CH2CH2CHO
c) methanol d) 2-methyl 2-propanol
c) CH3COCH2CH3
136. Sodium reacts with alcohol as given below
d) CH3COOH
2R -OH + 2Na ~ 2R-ONa + Hz
144. Lucas reagent is used to disting ish among primar
Place the type of alcohol into decreasing order of
secondary and tertiary
reactivity towards sodium.
a) alky halides b) alcohols
a) 30 > 20 >10 b) 10 > 30 > 2
c) aliphatic amines d) aromatic arnines.
c) 20 > 30 >10 d) 10 > 20 > 30

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145. The co pound which reacts faste with Lucas reagen (3) (CH3)3COH
at room temperature is These compounds are dehydrated by treatment
a) but n-1-01 with H2SO4, The correct sequence of increasing
b) but n-2-01 order of the reactivity of three compounds towards
dehydration is
c) 2-methyl propan-l-ol
a) 3 < 1 < 2 b) 1 < 2 < 3
d) 2-methyl propan-2-ol
c) 2 < 1 < 3 d) 1 < 3 < 2
146. t-butyl alcohol is heated with A12gives
154. Which of the following alkene on acid catalysed
a) CH3 – CH (CH3) CHCH3
hydration form propan-2-ol
b) CH3CH2CH = CH2
a) CH3CH = CH2
c) (CH3)2 C=CH2
b) (CH3)2C= CH2
d) all f these
c) (CH3)3CH = CHCHa
147. The compound which gives the most stable
d) CHaCH2CH = CH2
carboniurn ion on dehydration is
155. In isomeric alcohols correct order of boiling point
a) CH – CH3
is
b) (CH3)3C-OH
a) 2° > 3° >1° b) 3° > 2° >1°
c) CHl-CH2-CH2-CH20H
c) 1° >2° > 3° d) 20 > 1°>3°
d) C} 3Cl:I(OH)CH2CH;
156. Which one of the following compound would not
148. Maxin urn number of active h drogens are be oxidised by acidified K2Cr2O7?
b) ethyl alcoh 1 a) CH3OH b) (CH3)2CHOH
c) eth noic glycol d) glycerol
c) (CH3)3COH d) C2H5OH
149. When n-butyl alcohol is heated with Cu at 573 K,
157. Which of the following is expected to have highest
it for. boiling point?
a) butanal a) (CH3)2CHCI b) (CH3)2CHOH
b) propanal c) CH3CH2CH2OH d) CH3CH2CH2CI
c) ethyl methyl ketone
158. Final product by the treatment of isobutyl alcohol
d) 2-methyl propolene with alumina is,
150. 1-butanol is oxidiscd by acidified K2Cr2O7 give a) 2-methyl propene
a) butanal b) butanoic acid b) 2-methyl but-l-ene
c) butane d) butane c) ethyl t-butyl ether
151. Alcohols gives alkyl halides, treatment with methyl d) acetone and acetic acid
ketone?
159. Ethyl alcohol is heated with SOCl2 gives,
b) PX 5 b) PX 5 a) C2H5CI + HCI
c) HX d) all of the e b) C2H5CI + SO2
152. When 2-methyl 2-butanol is a dehydrated to give c) C2H5CI + HCI + SO2
an alkene, the preferred product is
d) CH3OH + CH3Cl + SO2
a) 2-methyl 2-butene
160. Isopropyl alcohol is oxidised by Cr03 gives,
b) 2-methyl 1-butene
a) CH3COCH3 b) CH3COOH
c) 2 methyl 1-butane
c) CH3CH = CH2 d) CH3CHO
d) n- methyl 1-propen
161. Which of the following is most acidic?
153. Consider the following compounds
a) H2O b) CHaOCH3
(1) CH3CH2CH2CH2OH
c) CH3OH d) C6H5OH
(2) CH3CH2CHOHCH3

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Alcohols, Phenols and Ethers 13

162. Which of the following is oxidised to form ethyl 171. In the following dehydration of alcohol (A) leading
methyl keton to the formation of syrene (B)
a) 2-propanol b) 2-butainol
H
c) 1-butanol d) 1-propanol CHCH3 
 H 2O
 CH=CH2
163. Which of the following is least solubnle in water?
a) CH3OH b) C3HOH a) hydrogen-bonding intermolecular attractions
c) C6H13OH d) C10H21 OH b) dipole-dipole attractios
164. Which of the following is more acidic alcohol? c) both of the above
a) C3H5OH d) none of the above
172. Which of the following functional groups can not
b) CH3– CH –CH be reduced by H2/Ni
|
OH a) R–CHO b) R–COOH
c) R–COO–R d) R–CO–R
c) CH3–CH2–CH2–OH
173. 3-ethyl pentan-3-ol is obtained by C2H5MgBr
d) (CH3)3–OH ,
and what?
165. Decreasing order of acidity of following alcohol
a) pentan 2-one b) pentane 3-one
c) pentanal d) 3-methyl butane-2one
1) 2) 173. 3-ethyl pentane-3-ol is obtained by C2H5MgBr and
OH OH what?
a) pentane 2-one b) pentane 3-one
3) 4) c) pentanal d) 3-methyl butane-2-one
OH
174. Acidic character of alcohols depends up on
a) 1 > 2 > 4 > 3 b) 3 > 1 > t > 2 a) Number of alkyl groups
c) 4 > 3 > 1 > 4 d) 1 > 2 > t > 3 b) polarity of –OH groups
166. Whidh of following is most acidic? I c) types of alkyl groups
a) H2O b) CH3–OH d) all of these
c) C2H5–OH d) C3H7–OH 175. Order of acidity of alcohol is
167. Which of the following is strong base? a) 1° > 2° > 3° b) 3° > 2° > 1°
a) CH3ONa b) NaOH c) 1° > 3° > 2° d) 3° > 1° > 2°
c) KOH d) Na2CO3 176. The B.P. of alcohols are much higher than the
168. Reactivity of alcohol in breakin O-H bond is ethers of comparable molecular masses due to
a) 1, > 2° > 3° b) 3° > 2° > ° a) Interamolecular H---bonding
0
c) 2 > 1° > 3° d) 10 > 3° > 12° b) Intermolecular H-bonding
169. Reactivity of alcohol in braking of C-O bond is c) dipole-dipole attraction
0 0
a) 1 > 2° > 3 b) 3° > 2° > 1 d) Hitler-London forces
0 0
c) 3 > 1° > 2° d) 1 > 3° > 2° 177. Which one is not characteristic of alcohols?
170. Boiling points of alcohols are gendrally high. This a) They are lighter than water
is dud to, b) Their B.P. rise uniformly with increasing
a) hydrogen-bonding intermolecular attractions molecular mass
b) dipole-dipole attractions c) Lower members are insoluble in water but
c) both of the above solubility increases regularly.
d) none of the above d) Lower members have pleasant odour and
burning test

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Alcohols, Phenols and Ethers 14

178. Consider following reactions, b) 1/2 gm of hydrogen
H
1. CH3CH2 CH CH3  A(major) c) 1.5 gm of hydrogen
| d) 2 m of hydrogen
OH 182. The dimer of methyl alcohol-will have structure

CH 3 H
| |
H
II. CH3 C  CHCH 3  a) H  O  C  H  CH 3
B(major)
|
| |
H
CH 3OH

A and B (both alkenes) are respectively b) CH 3  O.........O  CH 3

| |
CH 3 H H
|
a) CH3CH=CHCH3 HC3CHCH  CH 2 c) H–O–CH3....CH3 –O–H
| d) CH 3  O.........O  CH 3
CH 3 |
H

CH 3 183. Which of following has highest B.P?

| a) CH3–O–CH3 b) C2H5–OH
b) CH3CH2=CH= CH2 CH 3CCH  CH 2
c) C2H5–CI d) CH3–CHO
|
184. Which offollowing is the most viscous liquid?
CH 3
a) C2H5OH

c) CH3CH=CHCH3 CH3 C  CCH 3 CH 2  CH 2

| |
b) | |
CH 3 CH 3 OH OH

d) CH3CH2=CH2 CH3 C  CCH 3

CH 2  CH 2  CH 2
| |
CH 3 CH 3 c) | | |
OH OH OH
179. Glycero1 is more viscous than pro
d) HO –CH2(CHOH)4 CH2–CH – CH2
a) many hydrogen bonding per
185. Which of following exhibit highest B.P?
b) high B.P.
O OH
c) high molecular weight a) b)
d) more Lewis basic character
180. C2H2OH has higher B.P than, C2H5-SH due to
a) association c) d)
HO
b) dissociation
OH
c) low molecular mass
186. Which of the following is most soluble in water?
d) two lone pair of electron on oxygen
a) CH3–OH b) C2H5–Cl
181. When 1 mol of ethanol reacts wit sodium metal
c) CH3–O–CH3 d) C2H5–OH
liberate how many gram of hydrogen?
a) 1 gm of hydrogen

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Alcohols, Phenols and Ethers 15

187. Reason for excessive solubility of alcohol in water b) (CH3)2CH–CH2–CH2–OH
is due to
CH 3
a) covalent bonding
|
b) H-bonding with H20 c) CH 3  COH  C2 H 5
c) ionic bonding
d) all of these
d) Lewis base character
188. Alcohols of high molecular masses are 196. (CH 3 )2  C  CH 2  C(CH) 3 acidic

dichromate
a) high B.P and excessible solubility |
b) low B.P and excessive solubility OH
c) high B.P and low solubility the main product is
d) low B.P and low solubility
189. Compound with molecular formula C3H8O on CH 3 CH 3
vigorous oxidation produces an acid C5H6O2. It is | |
a) CH  C  CH  C  CH
a) 30 alcohol b) 20 alcohol 3 3
|
c) 10 alcohol d) not necessary CH 3
190. Which of the following reacts less emily with
sodium metal?
CH 3 CH 3
a) t-butyl alcohol b) isopropyl alcohol
| |
c) methyl alcohol d) ethyl alcohol
b) CH 2  C  CH 2  C  CH 3
191. Acetic acid and n-propyl alcohols has same |
molecular mass (60). Out of these two, which CH 3
have higher B.P?
a) Acetic acid b) n-propyl alcohol CH 3 CH 3
c) either d) neither | |
192. ZnCl2 in Lucas reagent is c) CH 3C  CH  C  CH 2
a) Lewis acid b) Lewis base
CH 3 CH 3
c) both 'a' and 'b' d) none of these
| |
193. Oxidation of 2-pentanone mainly produces d) CH 2  C  CH 2  C  CH 2
a) butyric acid and CO2+ H2O)
197. Ethanol is soluble in water to due to
b) acetic acid and propionic acid
a) ethyl group
c) propionic acid + CO2 + H2O
b) hydrogen bonding
d) acetic acid and propionic acid
c) Its neutral
194. The correct increasing of acidic strength
d) dissociation in water
a) CH3OH > H2O > (CH3)2 CHOH
198. The final product ofthe oxidation of ethyl alcohol
b) H2O > CH3OH > (CH3OH > H2 O
is
c) (CH3)2 CHOH > CH3OH > H2O
a) ethene b) acetone
d) H2O > (CH3)2 CHOH > CH3OH
c) acetaldehyde d) acetic acid
CH 3 199. Which has maximum pK value?
| a) ethene b) acetone
195. An alkyl halide CH 3  CCl  C2 H 2 can obts ined
c) acetaldehye d) acetic acid
by the action of HC] on which alcohol
a) (CH3)2CH–CH(OH)CH3

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Alcohols, Phenols and Ethers 16

OH 209. Tonic" generally contains,

OH a) enter b) methanol
200. 5 In this diol In this diol
2 c) ethanol d) rectified spirit
210. Dehydration is most easy for
a) OH at C2 is more basic than that of at C5
a) primary alcohols
b) OH at C2 is more acidic that at C5
b) tertiaryalcohols
c) both behave as a base
c) secondary alcohols
d) both behave as an acid
d) ethanol
201. When ethyl alcohol is oxidised by copper, then
211. The alcohol C4HgOH when s aken with a mixtu e
which of the following aldehyde is formed?
of anhydrous ZnCl2 and conc. HCI give an an
a) Formaldehyde b) Acetaldehyde immediate oil layer product.he alcohol is
c) Benzaldehyde d) Crotonaldehyde
a) H3 –(CH2)3–OH
202. The boiling point of a compound is raised by
b) H3 –CH(OH)CH2CH3
a) volatility of compound
c) (CH3)2CHCH2–OH
b) non-polarity in the molecules
d) (CH3)3C–OH
c) intermolecular hydrogen bonding
212. On oxidation of alcohol gives an a id having the
d) intramolecular hydrogen bonding
same umber of carbon atoms. The alcohol is,
203. The alcohol that is used as a beverage, is alcohol is
a) propanol b) butanol a) 10 alcohol b) 2° alcohol
c) ethanol d) methanol c) 30 alcohol d) not necessary
204. Wood spirit is known as 213. Secondary butyl alcohol is dehydr ted according
a) methanol b) ethanol to
c) acetone d) benzene a) Saytzeff rule
205. Solubility of alcohols in water depends upon b) Mark ownikoff rule
a) acidic nature c) Anti-Markownik off rule
b) basic nature d) none of these
c) neutral nature
214. Olefine are obtained from alcohol by heating
d) tendency to form hydrogen bonding
a) Al2O3 b) LiAlH4
206. Consider the following substances
c) B2 H6 d) NaBH4
a) 2-propanol, b) propanone
215. Cyclolexene is obtained from dehydration of
c) methyl amine
The correct sequence of increasing order of boiling OH
point is OH
a) b)
a) 2 < 3 < 1 b) 1< 2 <3
c) 2 < 1< 3 d) 3 < 2 < 1
207. Alcohols are miscible with H2O because of their OH
a) acidic character b) H-bonding c) d)
c) alkyl group d) dissociation OH
208. The reaction
216. 10, 20 and 30 alcohols are identified by
95% H 2SO 4
CH 3 CH 2 OH  CH 2 =CH 2 +H 2 O
453 K a) Lucus test b) oxidation test
is an example of c) haloform test d) all of these
a) de ydration b) dehydrog nation 217. Following alcohol on dehydration gives
c) hy ration d) decarbox lation

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Alcohols, Phenols and Ethers 17

223. When compound (A) is oxidised by acidic K2
OH Cr2O7 gave (B). Compound (B) on reduction
with LiAlH4 gave CAy.The compound (A) and
(B) are respectively
a) b) a) CH3–COCH3 and CH3–COOH
b) C2H50H and CH3–COCH3
c) C2H5OH and CH3–COOH
c) d) d) CH3–CHO and CH3 COCH3
224. The major product formed in following reaction
218. 3, 3-dimethyl butan-2-o1 on dehydration gives is
a) 3, 3-dimethyl but-2-ene
b) 2, 3-dimethyl but-2-ene
Na
c) 2, 3-dimethyl but-1-ene P  Br2
  A 
Ether
 (B)
d) 3, 3-dimethyl but-1-ene OH
219. The compound on oxidation gives ketone, the The compound
original compound is
a) 10 alcohol b) 20 alcohol
a) b)
c) 30 alcohol d) carboxylic acid
220. A organic compound (A) has pleasant odour, on
boiling (A) with cone. H2SO4 at 443K produces
colourless gas, which decolourises bromine water
c) d)
and Bayer's reagent. The original organic
compound (A) is
a) C2H5--CI b) C2H5–COOCH3 225. Which is best reagent to convert cyclohexanol
to cyclohexene
c) C2H5–OH d) C2R5-COOH
a) conc. HCl b) conc.HCI
221. The most suitable reagent to convert primary
c) conc. H2SO4 d) Lucas
alcohol to aldehyde
226. Inter following sequence of reaction
a) acidified K2Cr2O7
OH
b) alkaline KMnO4 P  I2
  (A) 
Mg / dry ether
 (B)
c) CrO3
(i) CH 3COCH 3
d) pyridinium chlorochromate (PCC)  
(ii) dry ether
(iii) H 3O 
(C). The compound (C) is
222. Following compound on dehydration gives
OH
a) OH b)
OH

OH OH
c) d)

227. C2H5COOH 

LiAlH 4 A
Al 2 O3
A 
623
 B + H 2O
a) b)
In above reaction A and B are respectively
a) C2H5–OH and CH2 = CH2
b) C2H5 –CHO and C2H5 OH
c) d) none of these c) CH3–CH2–CH2–OH
and CH3–CH = CH2

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Alcohols, Phenols and Ethers 18

228. In he sequence of reaction
CH 3
A  H 3O 
 B  |
C
Conc. H 2SO4
234. HBr
CH 3  C  CH CH 3   A (predo min ant), A is
OH | |
CH 3 OH
a) OH
and a) (CH3)3CCHCH3
b) (CH3)2CCH(CH3)2
OH c) both 'a' and 'b' C
and d) none is correct
b)
OH 235. 
NaBH CH=CHCHO
4
H 2 / Pt
CH=CHCHO   A

OH
a) CH2CH2CHO
c)
and

CH=CHCH2OH
d)
and

229. Dehydration of3-phenyl butan 2-0l gives CH2CH2CH2OH

a) 2-phenyl but 2-ene
b) 4-pheny12-methyl but-1-ene
b) CH=CHCH2OH
c) 1-pheny13-methyl but-1-ene
d) 1-phenyl but -1-ene
230. In dehydration of alcohol 1st step is c) CH=CHCH2OH in both cases
a) formation of carbonium ion
b) formation of carbonium
c) loss of proton from carbonium ion d) CH2CH2CH2OH in both cases
d) protonated of alcohol
236. When ,3 dimethyl 2-butanol under goes acid
231. Dehydration of alcohol produces alkene, the catalysed dehydration the roduct is,
section intermediate is reaction
a) 2.3 dimethyl 1-butene
a) carbonium ion b) 2,3 dimethyl 2-butene
b) carbanion c) 3,3 dimethyl 1-butene
c) carbon free radical d) none of these
d) carbene 237. Lucas reagent is
232. Denatured spirit is mainly used as a a) anhydrous ZnCl2 dissolved in conc. HNO3
a) good fuel b) hydrous ZnCl2 dissolved in conc. HCI
b) drug c) anhydrous ZnCl2 dissolved.in
c) solvent in preparing varnishes d) anhydrous ZnCl2 dissolved in dil HCl
238. Alcohols of low molecular weight are
d) material in the preparation of oil
a) insoluble in all solvents
233. Acetylation is a process in which the hydrogen of
b) insoluble in water
O–H group is replaced by
c) soluble in water at room temp rature
a) –C  C–H b) –CH = CH2
d) soluble in water on heating
c) –COCH3 d) –COC6H5

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Alcohols, Phenols and Ethers 19

239. 6 mole f ethyl alcohol reacts with odium metal. 248. 1, 1-diphenyl methanol is reacted with, HI give
How m ny moles of hydrogen are liberated? a) 1, 1-diphenyl iodomethane
a) 2 b) 3 b) 1, 1-diphenyl iodoethane
c) 4 d) 6 c) diphenyl
240. Catalytic oxidation of benzyl alcohol gives d) none of these
a) benzaldehyde b) benzoic acid 249. Which of the following is not dehydrating agent?
a) H2SO4 b) H3BO3
c) toluene d) phenol
c) ThO2 d) NaBH4
241. The ease of dehydration of alcohols in the order
250. Ethyl alcohol on heating with HI yield
a) 1° 2° > 3° b) 1° > 3° > 2
a) ethane b) ethylene
c) 3°2° > 1° d) 2° > 1° > 3
c) methane d) ethyl iodide
242. Alkene are obtained from alcoho s by 251. Product of the following reaction is
a) oxidation
COOH
b) hydration
K 2 Cr2 O7
c) intrmolecular dehydration LiALH 4
  A 
 dil.H 2SO4

d) intramolecular dehydration
243. Methanol and ethanol are in water due to a) benzaldehyde b) benzyl alcohol
a) dissociation in water c) toluene d) benzoic acid
252. The decreasing order of basicity of alcohols are
b) their acidic nature
a) 30 >20 > 1° b) 30 > 1° > 20
c) hydrogen bond with water
c) 2° > 3°> 1° C d) 10 > 20 > 30
d) alkyl groups
253. Which of the following alcohol reacts with HI by
244. When ethanol is treatedwith acid fied K2Cr2O7it SN1 reaction?
form acetic acid. It is an example of a) t-butyl alcohol b) methyl alcohol
a) oxidation b) oxidation c) n-propyl alcohol C d) ethyl alcohol
c) reduction d) rearrangement 254. Dehydration ofneophentyl alcohol gives
245. Which of the following compound react fastest a) 2-methyl but l-ene
with sodium metal? b) 3-methyl but-l-ene
a) H2O b) CH3–OH c) 2-methyl but 2-ene
c) C2H5–OH d) CH3–CH2–CH2–OH d) no product will be formed
246. Cyclohexanol is reacted with Lucas reagent gives 255. Which of the following can be used as dehydrating
a) 1-cyclohexyl chloromethane agent for alcohols?
a) H3PO 4 b) H2SO4
b) chlorocyclohexane
c) Al2O3 d) all of these
c) 1-chloroyclohexene
256. Which of the following compound will lose a
d) 1-chlorocyclohexyne molecule of water of treating with conc.
247. Following compound is reacted with cone. H2SO4 H2SO4?
at 363 K gives a) CH3COCH3 b) CH3COOH
c) CH3CH2OH d) CH3OCH3
a) b) 257. Which of the following is an example of
OH elimination reaction?
a) dehydration of alcohol
b) Chlorination of CH4
c) d)
c) Hydroxylation of C2H4
d) Nitration of benzene

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Alcohols, Phenols and Ethers 20

258. 23 g of sodium reacts with 1 mol methyl alcohol 269. The order of reactivity of following alcohols
to give towards HCl is,
a) half mola of H2 b) one mole of O2 1. CH3OH 2. CH3CH2CHPH
c) one mole of H2 d) either 'b' or 'c' 3. (CH3)2CHOH 4. (CH3)3COH
259. Which of the following compoune 'Will give a) 1 > 2 > 3 > 4 b) 4 > 3 > 2 > 1
ketone on oxlidation? c) 3 > 4 > 2 > 1 d) 2 > 4 > 1 > 3
a) CH3CH2CH2OH 270. Tertiary alcohols are resistant to oxidation because
b) CH3CH2CH(OH)CH3 a) they do not have a-hydrogen atom
c) (CH)3COH b) due to large + I effect of alkyl group
d) (CH3)2CH2CH2(OH) c) due to greater steric hindrance
260. Which of the following is most acidic? d) all of these
a) RCH2OH b) R2CHOH 271. Which of the following reactions shows acidic
c) R2C(OH)2 d) CH2OH nature of alcohols?
a) ROH + HOOCR  RCOOR + H2O
261. Lucas test is positive with
b) 2ROH + 2Na  2RONa + H2
a) CH3–O–CH3 b) C2H5OH
c) ROH + CIOCR  RCOOR
c) CH3–Cl d) CH3–CHO
d) ROH + HCI  RCI + H2O
262. The first product of oxidation of primary alcohol
is 272. Boiling point of alcohol is more than that of ether
of corresponding molecular weight, because
a) carboxylic acid b) ketone
a) alcohol being more soluble in water
c) ester d) aldehyde
b) ethers are non-polar solvent
263. Sodium metal reacts readily with
c) hydrogen bonding exist between alcohol
a) R –CHO b) R–CH2OH
d) none of these
c) ester d) R–NH2
273. Use of methanol may causes
264. KMn O4 acts as oxidising agent in
a) blindness and death due to its oxidation to CO2
a) acidic medium b) neutral medium b) blindness and death due to HCOOH
c) alkaline medium d) all of the above c) deficiency of calcium due to formation of salt
265. The group obtained by the removal of H-atom of d) disorder of blood hormones
the –OH group of ROH is caller
274. Which of the following compound does not react
a) alkyl group b) alkene with Lucas reagent?
c) alkoxy group d) all of these a) (CH3)3C–CHO b) (CH3)3C–OH
266. Alcohols are c) (CH)2CH–OH d) CH3–OH
a) neutral b) strongly acidic 275. The final subsidiary product in the following
c) basic d) amphoteric reaction is, R–OH + PX3 R 

X+?
267. Which one of the following on oxidation gives a a) H3PO 3 b) HX
ketone?
c) H 3PO 4 d) HPO4
a) Primary alcohol b) Secondary alcohol 276. Which one of the following process is used to
c) Tertiary alcohol d) All of these distinguish between the three tyres of alcohols?
268. Correct order of increasing boiling points is a) Reduction b) Hydrolysis
a) propane < n-butane < ethanol < water c) Oxidation d) Hydrogenation
b) propane < ethanol < n-butane < water 277. Keton is the first oxidative product of
c) water < ethanol < propane < n-butane a) 10 lcohol b) 30 alcohol
d) water < propane < n-butane < ethanol c) 20 alcohol d) acid

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Alcohols, Phenols and Ethers 21

278. The compound which liberates H2 gas with sodium a) CH3–OH and C2H5–OH
metal is b) CH3–CHO and CH3–OH
a) aldehyde b) ethanol c) CH3–CHO and CH3–CHO
c) ether d) ketone d) C2H5–OH and C2H5–OH
279. 1-proponol is converted into propene, which of 288. Find out correct reducing agent in following
the following agent is used? conversion.
a) alc KOH b) dil. NaOl CH3–CH2–CH2–COOH 
CH3–CH2–CH2–CH2–OH
c) dil. HCI d) cone. H2SO4
a) H2 + Ni b) NaBH4
280. Optical isomer of molecular formula C4H10O on
c) NaHg + H2O d) LiAlH4
-elimination gives
289. Compound A (ester) reacts with LiA1H4 gives B
c) bu anal b) 2-methyl ropanal
and C. Compound Bon oxidation gives acetic acid
c) 2-butanone d) 2-methyl propene and compound C on oxidation gives formic acid.
281. Which of the following is associated liquids? The compound 'A' is
a) ROH b) H2O a) C2H5–COOCH3
c) RNH2 d) All of thede b) CH3COOC2H5
282. Methyl alcohol on oxidation with acidified c) CH3–COOCH3
K2Cr2C7 gives d) CH3–CH2–COOH
a) CH3CHO b) HCOOH 290. Which ofthe following compound have covalent
c) CH3COCH3 d) CH3COOH and ionic bond ?
a) R-OH b) H-O-H
283. 2-buta 1101 on dehydration mainly gives,
c) R-X d) R-ONa
a) CH3CH2CH = CH2
Al 2 O3
b) CH3CH = CHCH3 291. (CH 3 ) 2 CH  CH  CH 3  X
c) (CH3)2 C=CH2 Give the IUPAC name of major product formed
in the reaction
d) CH3CH=CH2
a) 3-methyl 2-butene b) isobutylene
284. I-propanol can be converted into I-chIaro propane
c) 2-methyl 2-butene d) 2-methyI1-propene
by HCl in the presence of catalyst
292. Which of the following is/are correct?
a) hye rous ZnCl2 b) unhydrou: ZnCl2
a) Absolute alcohol is 100% ethanol.
c) H3PO 4 d) P 2O 5
b) The alcohol sold in the market for polishing is
285. Oxidation mean known as methylated spirit
c) addition of oxygen c) Ordinary ethanol is known as rectified spirit
b) increase in oxidation state d) All of these
c) loss of electron 293. Mixture of acetic acid and projpionic acid is
d) all of these obtained from oxidation of
286. Which statement is not correct about the alcohols? a) CH3–COCH3
b) CH3-COC2H
a) Alcohols involves H-bonding
c) CH3–CH2-COCH2–CH3
b) Alcohols evaporates quickly than water
d) CI3–CH2-CHO
c) Alcohols ofless number of carbon atoms are
294. An organic compound (A) produces
less soluble than more number of carbon
The compound A is
atoms
a) (CH3)CCH2–OH
d) All of these
b) (CH3)2COHCH2–CH3
287. Product 'B' of the following reaction is
c) (CH)2CH–CHOHCH3
CH3+ Cl + CH3–CI + CH3–COOAg  B d) All of these

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295. The hydrogen bonding ability of 1°, 2° and 3° c) ether has two hydrophobic group while alcohol
alcohols is of the order has one
a) 30 > 2° > 1° b) 10 > 2° > ~o d) ether has two hydrophilic group while alcohol
0
c) 3 > P 20 0
d) 1 > 3° > 2° has one
296. When 3-methyl 3-pentanol i heated with aluminum 303. Lucas test is used to distinguish between 1°,2°,
The main product formed is and 3° alcohols. This shows that
a) 2 methy1 1-pentene a) R-OH behaves as base
b) 3 methyl 2-pentene b) greater the Pka value of alcohol, greater the
reactivity of alcohol with HCI and thus sooner
c) 2 methy1 1-butene
the formation of white turbidity
d) 3 methyl 2-butene
c) both are correct
297. An organic compound X reacts with sodium metal
d) none is correct
and volve hydrogen gas, on osiidation of X by
PCC give aldehyde. The formul of X could be 304. The most suitable reagent for conversion of
R–CH2–OH  R–RHO is
a) (CH3)2CH–OH b) CH3–CH2–OH
a) neutral KMnO4 b) PCC
c) (CH3)2C–OH d) CH3–C–OHC2H5
c) acidic K2Cr2O7 d) CrO3
298. 2-butanol conc H2SO4 1- butene + 2 – butene
Which are correct statements? CH 3
a) A is Saytzelfproduct B is not |
K 2 Cr2 O7 CH 3MgI
b) A is Saytzelfproduct B is not 305. A 
dil. H 2SO 4
 B 
H 2O
 CH  C  CH
3 3

c) Either 'a' and 'b' |

OH
d) Neither
299. Which of the following is maximum basic? The reactant A is
a) (CH3CH2–CH2–CH2–OH The reactant A is
b) (CH3)2CH–CH2–OH a) CH3CHOHCH3 b) CH3COCH3
c) CH3CHOHC2H5 c) C2H5OH d) CH3COOH
d) CH3)3C–OH 306. For the reaction C2H50H + HX 
ZnX 2
 C2H5X.
300. The C4H10O (alcohols) produc s immediate X The order of reactivity is D
terbidity with Lucas reagent the alcohol is
a) HBr > HI > HCI b) HI > HCI > HBr
a) CH3–CH2–CH2–CH2–OH
c) HI > HBr > HCI d) HCI > HBr > HI
b) (CH3)2CH–CH2–0H
307. Ethanol is converted into ethyl chloride by reacting
c) (CH3CHOHC2H5 with
d) (CH3)3C–OH a) POCl3 d) SOCl2
301. Solubility of alcohol in water is due to 308. Which of following reducing agent is used to
a) hydrophobic R-group convert carboxylic acid into alcohol?
b) hydrophilic OH-group a) Na.Hg + H2O b) LiAlH4
c) hydrophobic OH-group c) NaBH4 d) Sn + HCI
d) hydrophilic R-group 309. Primary, secondary and tertiary alcohols may be
302. Boiling point of ethanol is greater than isomeric distinguished by employing
ether is due to a) Hoffmann's test
a) hydrogen bonds are much stronger than dipole- b) Fehling solution test
dipole attraction c) Lucas test
b) dipole-dipole attraction is much stronger than d) None of the above
hydrogen bond

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310. Oxidation of ethanol by chromic acid forms 317. In reaction of alcohols with alkali metal which of
a) ethanal the following alcohols will react fastest
b) methanel a) secondary b) tertiary
c) 2 propanone ethanoic acid c) primary d) all equal
d) ethanoic acid 318. The -OH group of methyl alcohol cannot be
311. Conc.H2SO4 reacts with C2H5OH at 443 K toform replaced by chlorine by the action of
a) CH3COCH3 b) CH3COCH a) chlorine
c) CH3CHO d) C2H4 b) hydrogen chloride
312. Distinction between primary, secondary and c) phosphorus trichloride
tertiary alcohol is done by d) phosphorus pentachloride
a) oxidation method b) Lucas test 319. When ethanol is passed over red hot copper at
c) silver mirror test d) both 'a' and 'b' 573K, the product formed is
313. Low molecular weight alcohols are a) CH3CHO b) CH3COCH3
a) soluble in water c) C2H4 d) CH3COOH
b) soluble on heating 320. A mixture of methanol vapours and air is passed
c) insoluble in water over heated copper. The products are
d) insoluble in all solvent a) carbon monoxide and hydrogen
314. Isopropyl alcohol on oxidation fcrms b) formaldehyde and H2 gas
a) acetone b) ether c) formic acid and water vapour
c) ethylene d) acetaldehyde d) carbon monoxide and water vapour
315. Among the following compound which can be 321. When ethyl alcohol reacts with thionyl chloride in
dehydrated very easily is the presence of pyridine, the product obtained is
a) CH3CH2CI + HCI
CH 3
| b) C2H5CI + HCI + 802
a) CH3–CH2 – C  CH 2  CH 3 c) CH3CH2CI + H20 + 802
| d) H3CH2CI + Cl2 + 802
ON 322. Primary alcohols on dehydration give
a) alkenes b) ether
OH
| c) alkane d) ester
b) CH3–CH2–CH2– CH –CH 323. Primary and secondary alcohols on action of
c) CH3–CH2–CH2–CH2–CH – OH reduced copper give
a) aldehydes and ketones respectively
d) CH3–CH2– CH –CH2–CH2 –OH
b) ketones and aldehydes respectively
|
CH 3 c) only aldehydes
d) only ketones
316. Which of the following is not characteristic of
324. Methyl alcohol on oxidation with acidified
alcohols ?
K2Cr2O7gives
a) Lower alcohols are stronger and have bitter
a) CH3COCH3 b) CH3CHO
taste
b) Higher alcohols are stronger and have bitter c) HCOOH d) CH3COOH
taste 325. Ethyl alcohol on oxidation with Cr2O7 gives
c) The boiling points of alcohols increase with a) acetic acid b) acetaldehyde
ircreasing molecular mass c) formaldehyde d) formic acid
d) The lower alcohol are soluble in water

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326. On heating ethanol with excess of cone. H2SO4 at 333. Seperation of two layers are seen when Lucas
443K, product obtained is reagent is treated with
a) ethene b) ethane a) CH3OH b) CH3Cl
c) ethyne d) ethoxy ethane c) (CH3)3C–OH d) (CH3)3C–Cl
327. When 3, 3-dimethyl 2-butanol is heated with 334. Aluminium metal reacts with a acohol gives
H2SO4 major product obtained s a) ROAl b) (RO)2Al
a) 2 ,3-dimethyl l-butene c) (RO)3 Al d) RCOAl
b) 3,3-dimethyl 335. When six mole of alcohol reacts with aluminium
c) 3-dimethyI 2-butene metal. How many gram of hydrogen is liberated?
d) cis and trans isomers of 2, 3-dimethyl -butene a) 2 b) 4
328. Which of the following will giv benzoic acid on c) 5 d) 6
oxid tion? 336. Ethyl alchohol is reacted with acetyl chloride gives
a) enzyl alcohol b) Benzal ehyde a) ethyl acetate b) ethyl formate
c) cetophenone d) All of tl ese c) ethyl propanoate d) ethyl methyl ketone
329. n-pr pyl alcohol and isopropy alcohol can be 337. Methy acetate is formed from methyl alcohol and
chemically distinguished by which reagent what?
a) Cl5 a) Acetic acid b) Acetic unhydride
b) reduction c) Acdtyl chloride d) All of these
c) oxidation with potassium chromate H 
338. C2H5OC + A C 2H 5C O O C 2H 5+
d) Cl3
C2H5COOH
330. Which of the following of alcohols are
distinguished by oxidation test Lucas test and The compound 'A'
haloform test? a) C2H5COCl b) (C2H5CO)2O
a) ethanol and ethanol c) C2H5COOH d) C2H5CHO
b) ethanol and 3-pentanol
c) ethanol and 2-propanol
d) 1-propanol and 3-pentanol
331. Consumption of alcohol by wide drivers is detected
by
a) low of mouth are in test tube containing acidic
K2Cr2O7
b) low of mouth air in test ube containing alcoholic
KOH
c) blow of mouth air in test tube containing Cu20
d) low of mouth air in test ube containing chiff's
reagent.
332. Which of the following s pyridinium
chlorochromate ?
a) 6H5NH + CrO3CI
b) C5H5NH + CrO3CI
c) C6H5NH+CrO3Cl
d) C5H5SO2Cl

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1. (a) 2. (b) 3. (b) 4. (b) 5. (c) 6. (b) 7. (d) 8. (d) 9. (a) 10. (c)
11. (c) 12. (b) 13. (c) 14. (b) 15. (b) 16. Cd) 17. (b) 18. (c) 19. (c) 20. (b)
21. (b) 22. (b) 23. (c) 24. (d) 25. (c) 26. (b) 27. (a) 28. (a) 29. (c) 30, (a)
31. (b) 32. (d) 33. (b) 34. (c) 35. (c) 36. (a) 37. (d) 38. (b) 39. (b) 40. (c)
41. (b) 42. (b) 43. (d) 44. (c) 45. (d) 46. (b) 47. (c) 48. (d) 49. (a) 50. (d)
51. (d) 52. (c) 53. (a) 54. (c) 55. (d) 56. (d) 57. (c) 58. (b) 59. (c) 60. (d)
61. (a) 62. (b) 63. (b) 64. (a) 65. (d) 66. (b) 67. (c) 68. (a) 69. (b) 70. (a)
71. (d) 72. (b) 73. (a) 74. (c) 75. (a) 76. (b) 77. (d) 78. (b) 79. (b) 80. (a)
81. (d) 82. (b) 83. (d) 84. (b) 85. (d) 86. (c) 87. (d) 88. (c) 89. (a) 90. (a)
91. (b) 92. (b) 93. (c) 94. (c) 95. (a) 96. (a) 97. (b) 98. (c) 98. (a) 100. (d)
101.(d) 102. (a) 103. (b) 104. (a) 105. (b) 106. (b) 107 (a) 108. (d) 109 (d) 110. (d)
111. (c) 112. (c) 113. (a) 114. (a) 115. (b) 116. (a) 117 (c) 118. (b) 119. (b) 120. (d)
121.(d) 122. (c) 123. (b) 124. (d) 125. (c) 126. (b) 127. (d) 128. (a) 129. (b) 130.(c)
131.(a) 132. (d) 133. (b) 134. (b) 135. (d) 136. (d) 137. (c) 138. (a) 139. (a) 140. (d)
141.(b) 142. (a) 143. (b) 144. (b) 145. (d) 146. (c) 147. (b) 148. (d) 149. (d) 150.(b)
151.(d) 152. (a) 153. (b) 154. (a) 155. (c) 156. (c) 157. (c) 158. (a) 159. (c) 160. (a)
161.(d) 162. (b) 163. (d) 164. (a) 165. (d) 166. (a) 167 (a) 168. (a) 169. (b) 170. (c)
171.(d) 172. (b) 173. (b) 174. (d) 175. (a) 176. (b) 177 (c) 178. (c) 179. (a) 180. (a)
181.(b) 182. (d) 183. (b) 184. (d) 185. (b) 186. (a) 187 (b) 188. (c) 189. (c) 190. (a)
191.(a) 192. (a) 193. (b) 194. (b) 195. (d) 196. (a) 197 (b) 198. (d) 199. (d) 200. (a)
201.(b) 202. (c) 203. (c) 204. (a) 205. (d) 206. (a) 207. (b) 208 (a) 209. (c) 210. (b)
211.(d) 212. (a) 213. (a) 214. (a) 215. (a) 216. (d) 217 (d) 218. (b) 219. (b) 220. (c)
221.(d) 222. (b) 223. (c) 224. (c) 225. (c) 226. (d) 227 (c) 228. (a) 229. (a) 230. (d)
231.(a) 232. (c) 233. (c) 234. (b) 235. (b) 236. (a) 237 (c) 238. (c) 239. (b ) 240. (a)
241.(c) 242. (d) 243. (c) 244. (b) 245. (a) 246. (6) 247 (c) 248. (a) 249. (d) 250. Cd)
251.(d) 252. (a) 253. (a) 254. (c) 255. (d) 256. (c) 257 (a) 258. (a) 259. (b) 260. (d)
261.(b) 262. (d) 263. (h) 264. (d) 265. (c) 266. (a) 267 (b) 268. (a) 269. (b) 270. (a)
271.(b) 272. (c) 273. (b) 274. (a) 275. (a) 276. (c) 277 (c) 278. (b) 279. (d) 280. (c)
281. (d) 282. (b) 283. (c) 284. (b) 285. (d) 286. (c) 287 (a) 288. Cd) 289. (c) 290. (d)
291.(c) 292. (d) 293. (c) 294. (d) 295. (b) 296. (b) 297 (b) 298. (b) 299. (d) 300. (d)
301.(b) 302. (a) 303. (c) 304. (b) 305. (a) 306. (c) 307 (b) 308. (b) 309. (c) 310. (d)
311.(d) 312. (d) 313. (a) 314. (a) 315. (a) 316. (b) 317 (b) 318. (a) 319. (a) 320. (b)
321.(b) 322. (a) 323. (a) 324. (c) 325. (a) 326. (a) 327 (c) 328. (d) 329. (c) 330. (b)
331.(a) 332. (b) 333. (c) 334. (c) 335. Cd) 336. (a) 337 (a) 338. (b)

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Section II : Ethers a) propoxy methyl
Introduction, Nomenclature, Classification b) 2-methoxy propane
Isomerism c) 1-methoxy propane
1. An ether is d) methyl propanoate
a) R–O–R' b) RCOR
12. According to Lewis concept of acids and bases,
c) RCHO d) RCOOR ether is
2. The monovalent RO group is called a) acidic b) basic
a) alkyl group b) alkoxy group c) neutral d) amphoteric
c) alkenyl group d) all of these 13. What is IUPAC name of compound when divalent
3. Which of the following is a simple ether? oxygen atom is attached to n-propyl group and
a) CH3OC2H5 b) C2H5–OC2H5 iso-propyl group ?
c) C2H5OC3H7 d) CH3CH2OCH(CH3)2 a) propoxy 2-propane
4. Which of the following is an unsymmetrical ether? b) Propoxy ethane
a) CH3–O–C3H7 b) CH3–O–CH3 c) 1 (2-propoxy) propane
c) C2H5–O–C2H5 d) All of these d) 1-ethoxy butane
5. An example of a compound with the functional 14. Ethers have angular V-shaped geometry like
group –O– is
a) NH3 b) H2O
a) acetic acid b) methyl alcohol
c) CH4 d) CH3+
c) diethyl ether d) acetone
15. The IUPAC name of CH3OCH(CH)2 is,
6. In R'–O–R, the R' is a higher alkyl group, it is
come from a) 2-methoxy propane
a) alkane b) alcohol b) 2-epoxy propane
c) both 'a' and 'b' d) not predicted c) 2-methoxy propane
7. The IUPAC name of C2H5OCH2CH(CH3)2 is d) 1-epoxy propane
a) 3-ethoxy 2-methyl propane 16. IUPAC name of the following compound is
b) 1-ethoxy 2-methyl propane
O
c) 1-ethoxy butane
d) 2-ethoxy butane
8. IUPAC name of the following compound
(CH3)2CHOC(CH3)3 is a) 2-pentoxy benzene
a) t-butyl isopropyl ether b) phenetol
b) 2, (2-propoxy) 2-methyl propane c) 2-phenoxy pentane
c) 2 methyl 1-ethoxy 2-propane d) isopentyl phenyl ether
d) 1methyl 2-propoxy 2-propane 17. IUPAC name of the following compound is
9. IUPAC name of ether is
O
a) alkyl alkanoate b) alkoxy alkane
c) a kanamine d) alkyl acetate
10. IUPAC name of CH3–O–C2H5 s
a) ethoxy methane a) 1-heptoxy benzene
b) methoxy methane b) heptyl phenyl ether
c) methoxy ethane c) 1-phenoxy heptane
d) ethyl methyl ether d) 2-phenoxy heptane
11. IUPAC name of methyl n-propy ether is

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18. Ethers are 27. Diethyl ether exhibits metamerism with
a) Lewis acid b) acid a) CH3OCH2CH2CH3
c) Lewis base d) base b) CH3OCH(CH3)2
19. IUPAC name CH3–O–C(C2H5)3 is c) both 'a' and 'b'
a) 3-methoxy 2-ethyl pentane d) CH3COC2H5
b) 2-methoxy 2-ethyl pentane 28. Ethers are isomeric with
c) 3-methoxy 3-ethyl pentane a) aldehydes b) alcohol
d) 2-methoxy 3-ethyl pentane c) acids d) ketone
20. How many metamers are possible for molecular 29. CH3CH2CH2OH is functional isomer of
formula C4H10O?
a) ethyl methyl ether
a) 3 b) 7
b) ethyl n-propyl ether
c) 5 d) 2
c) methyl n-propyl ether
21. Following compounds are :
d) 2-propanol
O
and 30. The compound which is metame of diethyl ether
O
is
a) chain isomer b) linkage isomers a) 1-methoxy propane
c) position isomer d) functional isomers b) 1-butanol
22. IUPAC name offollowing compound is c) 2-methoxy propane
(CH3)3C–O–CH2CH(CH3)2 d) both 'a' and 'c'
a) 2 (2-methyll-propoxy) 2-methyl propane 31. The compound is not isomeric mth diethyl ether
b) 1 (2-methy12-propoxy) 2-methyl propane a) 1-butenol
c) 1 (2-propoxy) 2-methyl propane b) 2-propanol
d) 2 (2-propoxy) 2-methyl propane c) 2-methy1 2-propanol
23. IUPAC name of ethyl t-butyl ether is d) 2-butanol
a) 2-ethoxy propane 32. 1-methoxy propane and 2-methoxy propane are
b) 2-ethoxy 2-methyl propane a) position isomers
c) 2-ethoxy 2, 2-dimethyl prop ne b) chain isomers
d) 2-ethoxy 1-methyl propane
c) metamers
24. The compounds
d) functional isomers
CH3 –O–C3H7 and C2H5–O–C2H5 exhibit
33. Dimethyl ether is associated with which one of
a) metamerism the isomer?
b) chain isomerism a) Ethanol b) Methanol
c) optical isomerism
c) Formic acid d) Methyl formate
d) cis-trans isomerism
34. Molecular formula C4H10O exhibits
25. Moleular formula C4H10 O has _____ isomeric
a) chain isomerism b) position isomerism
ethdrs
c) metamerism d) all of these
a) 4 b) 3
35. Which of the following compound shows
c) 7 d) 5
metamerism ?
26. The compound which is not ison eric with diethyl
ether is a) CH3OCH3 b) CH3O C3H7
a) butan-l-ol b) 2-methy1propan-2-ol c) CH3C2H5 d) CH3COC2H5
c) butanone d) n-propyl methyl ether 36. Ethers do not show

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a) chain and position isomers 46. Which of the following compound does not show
b) chain and metamers metamerism ?
c) position isomers a) CH3–O–CH3 b) CH3–O–C4H9
d) optical isomers c) CH3–O–C3H7 d) CH3–O–C5H11
37. Diethyl ether can be distinguish from butan-1-ol 47. Following compound can be named as
by CH3–O–(CH2)4CH3
a) aq. FeC13 b) Na metal OH
c) Tollens reagent d) Fehling reagent
O
38. C6H5–O–CH3 can be named as
a) phenoxy methane a) 3-methoxy pentane
b) phenetole b) 2-methoxy pentane
c) methoxy phenyl c) 4-methoxy pentane
d) methoxy benzene d) 1-methoxy pentane
39. Ethers and alcohols are 48. Following compounds are
a) metamers b) functional isomers a) metamers b) position isomers
c) tautomers d) position isomers c) chain isomers d) functional isomers
40. Which isomerism is possible in ethers? 49. How many mctamers are possible for molecular
a) Tautomerism b) Chain isomerism formula C5H12O
c) Metamerism d) Position isomerism a) 4 b) 6
41. Which of the following compound show c) 8 d) 10
metamerism ? 50. How many ethers are possible for molecular
a) CH3–O–CH3 b) CH3–CO-CH3 formula C5H12O
c) CH3NHCH3 d) CH3–O–C3H7 a) 12 b) 14
42. Metamerism is advance type of c) 8 d) 6
a) optical isomerism 51. IUPAC name of following compound is
b) geometrical isomerism O O
c) chain and position isomerism
d) only chain isomerism O
43. Ether shows a) 1, 3, 5 trimethoxy pentaane
a) chain and position isomerism b) 2, 4, 8 trioxa nonane
b) metamerism and optical isomerism c) 1, 3, 5 trimethoxy heptane
c) chain and metamerism d) 1, 3, 5 trimethoxy hexane
d) position and metamerism 52. Hydride of ether is
44. Following compounds are a) aldehyde b) alcohol
a) functional isomers c) ketone d) carboxylic acid
b) metamers
Preparation Methods
c) chain isomers
53. The reaction of CH3CH2Br and (CH3)3CONa to
d) position isomers
form ether is called
45. Metamerism is possible in
a) Williamson reaction
a) same polyvalent function group
b) Wurtz reaction
b) same monovalent functional group
c) Cannizzaros reaction
c) different polyvalent functional group
d) Hoffmans reaction
d) different monovalent functional group

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54. Which of the following reaction does not form 60. Catalytic dehydration of ethanol a 413 K gives :
ether? a) ethene b) ethoxy ethane
a) RX + aq. KOH c) ethane d) epoxy ethane
b) RX + RONa 61. Preparation of ether from ethanol by continuous
c) CH2N2 + ROH etherification process is
d) ROH + H2SO4 at 413 K a) SN reaction b) SN2 reaction
55. Reaction between sodium ethoxide and c) E1 reaction d) E2 reaction
bromoethane forms 62. Willian son's reaction of 30 alkylhalide is
a) ethyl methyl ether b) diethyl ether a) SN reaction b) Elimination reaction
c) dimethyl ether d) acetic acid c) SN reaction d) Reduction
56. Williamson's reaction is 63. Density of ether is
a) SNl reaction of R–X a) higher than water b) equal to water
b) SN2 reaction of R–X c) lower than water d) can't be predicted
2
c) SN reaction of alkoxide 64. Sodium phenoxide is reacted with ethyl chloride
d) dehydration of R–X gives
57. In Williamson reaction intermediate formed is a) o-ethyl sodium phenoxide
a) carbocation b) free radical b) p-ethyl sodium phenoxide
c) carbanion d) T.S c) ethoxy benzene
58. Select incorrect statement about following about d) methyl sodium phenoxide
reaction of ether synthesis : 65. Methoxy benzene is prepared from CH3–Cl and
R  X  R 'ONa 
 ROR ' NaX a) phenol b) sodium benzoate
a) It follows SN2 mechanism c) sodium phenoxide d) benzyl chloride
b) Alkyl halide (RX) should be 20 or 30 while 66. Which is the leaving group in the following
alkoxide (RO– Na+) should be 10 reaction?
HBF4
c) Alkyl halide should be 10 while alkoxide should CH3OH  CH 2 N 2  
be 20 or 30.
a) H2O b) N2
d) 2 0 and 3 0 alkyl halide may undergo E 2

elimination in the presence of a strong base to c) C H3 d) H+
form alkenes.
67. In the preparation of ether, one of the reactant in
59. Consider following reaction :
R–X another is
a) alc. R–ONa b) moist Ag2O
I. ONa + CH2 I 
c) CH2N2 d) RCOONa
68. Select correct statements about fol owing reaction:

H
II. Br + CH3 ONa  2R  OH  R  O  R  H 2O
a) It is an example of SN reaction in which
III. (CH3 )3 C  Cl  CH3ONa 
 protonated alcohol is the substrate and second
molecule of alcohol is the nucleophile.
IV. (CH3 )3 C  ONa  CH 3Cl 

b) It is intermolecular dehydration of alcohols.
Which of the above methods cannt be used in the c) This reaction can be SN2 if alcohol is 10.
synthesis of ether?
d) Al1 of the above statements are corrects
a) I, IV b) I, II
c) II, IV d) II, III

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69. Continuous etherification process based upon 78. In Williamson's Synthesis
a) oxidation a) sodium alkoxide is treated with alkyl halide.
b) intermolecular dehydration b) sodium metal is treated with alkyl halide.
c) intramolecular dehydration c) an excess of alcohol is heated with conc.
d) reduction Al2SO4 at 413 K
d) vapours of alcohol are passed over heated
70. In continuous etherification process 1st step is
Al2O3 at 633 K
a) formation of carbocation
79. Excess of ethanol is heated with conc. H2SO4 at
b) protonation of alcohol
413 K. The compound that disills is
c) loss of proton from oxocation a) diethyl sulphate
d) cleavage of O–H bond in alcohol b) diethyl ether
71. Consider the following alkyl halides c) ethylene hydrogen sulphate
a (CH3)3 CBr b) CH3Br d) ethylene
c) C2H5Br d) CH3CHBrCH3 80. 1-butanol is reacted with diazmethane to give
72. When ethyl hydrogen sulphate is heated with a) 1-methoxy butane
ethanol at 413 K, the product formed is b) 2-methoxy butane
a) ethyne b) ethene c) l-ethoxy butane
c) diethyl ether d) diethyl sulphate d) 2-ethoxy butane
73. Diethyl ether is conveniently prepared in 81. Which of the following statement(s) is/are true
laboratory from about Williamson's Synthesis?
a) diazomethane a) It is desirable to use primary R–X
b) continuous etherification process b) This method is particularly used for preparation
c) Williamson's synthesis of mixed ether.
d) all of these c) It is best to use the alkoxide of 20 and 30
alcohols.
74. In Williamsons synthesis t-alkyl halide can not be
d) all of these
used for preparation of alkyl t-butyl ether, because
82. 2-Ethoxy propane is effectively prepared from
a) it is difficult to remove halogen atom
a) isobutyl iodide b) isopropyl iodide
b) the reaction become reversible
c) ethyl iodide d) n-propyl iodide
c) it is not reactive
83. The reaction between C2H5ONa + C2H5 I to give
d) it readily decompose to give olefin C2H5OC2H5 is called
75. Which of the following pair is used to prepare a) Wurtz Reaction
2-ethoxy 2-methyl propane?
b) Kobles Synthesis
a) (CH3)3CCl + C2H5ONa c) Williamson Synthesis
b) (CH3)3CONa+ C2H5Cl d) Hoffman Reaction
c) CH3CH2ONa + C2H5Cl 84. The reaction of alkali alcoholate and monohalo
d) CH3CH2CH2ONa + C2H5Cl alkane is called as
76. Ethyl iodide on treatment with sodium methoxide a) Wurtz Reaction
gives b) Cannizzaro's reaction
a) CH3–O–CH3 b) C2H5OCH3 c) Williamson's Synthesis
c) C2H5OC2H5 d) C2H6 d) Aldol Reaction
77. In the preparation of aromatic ether one of the 85. Williamson's synthesis is used to prepare
reactant is sodium phenoxide, another is a) diethyl ether b) amine
a) R–OH b) R–Cl d) ethanol d) ethanal
c) R–CHO d) R–COONa

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86. The intermediate product obtained during 95. When an alkyl halide is allowed to react with a
continuous etherification process is, sodium alkoxide the product most likely?
a) alkyl hydrogen sulphite a) An a dehyde b) A ketone
b) alkyl hydrogen sulphate c) An ether d) A carboxylic acid
c) alkyl sulphate Properties and Uses
d) alkyl sulphite
96. When ethyl methyl ether is reacted with cold conc.
87. Reaction of t-butyl bromide with sodium
HI gives ethanol and methy iodide. The reaction
methoxide produces
proceeding through
a) sodium tertiary butoxide
a) SNl b) SN2
b) tertiary butyl methyl ether
c) El d) E 2
c) isobutane
97. When t-butyl methyl ether is reac ed with cold
d) isobutylene conc. HI to give t-butyl iodide and methyl
88. Excess of isopropyl alcohol is heated with conc. alchohol. The reaction proceeding through
H2SO4 at 413 K, gives a) SNl b) SN2
a) (CH3)2CHOCH(CH3)2 b) CH3CH = CH2 c) E 1 d) E 2
c) both 'a'and 'b' d) none of these 98. Halogenation of anisole is carried in the presence
89. From Williamsons synthesis, which one of the of catalyst
following is most desirable to prepare ether? a) FeC3 b) AlC13
a) 30 R–X and alkoxide of 10 alcohol c) BF3 d) CH3COOH
b) 30 R–X and alkoxide of 10 alcohol 99. Bromination of anisole gives majo product
c) 20 R–X and alkoxide of 10 alcohol a) o-bromoanisole b) p-bromoanisole
d) 10 R–X and alkoxide of 30 alcohol c) m-bromoanisole d) di-orthobromoanisole
90. Methoxy ethane is obtained by C2H5OH and what? 100. Nitration of phenyl alkyl ether gives
a) CH3Cl b) CH3ONa a) o-nitro alkyl phenyl ether
c) CH2N2 d) CH2Cl2 b) o-nitro alkyl phenyl ether
91. Intermolecular dehydration of alcohol gives c) mixture of ortho and para nitro phenyl alkyl
a) Alkenes b) Ethers ether
c) Alkynes d) Aldehydes d) m-nitro alkyl phenyl ether
92. In the formation of ether, one of the compound is 101. Product of following reaction is
alcohol is
O dil. H 2SO 4
a) R–ONa b) CH2N2  
c) R–OAg d) R–OK a) C2H5OH b) CH3CHOHPH3
93. The reaction given below is known as c) C2H5OSO3H d) CH3CH2CH2OH
C2H5ONa + IC2H6  C2H5OC2H5 + NaI 102. Which of the following ether produces methyl
a) Kolbe's synthesis alcohol when reacts with cold HBr
b) Wurtz's synthesis a) 2-methyl 2-methoxy propane
c) Williamson's synthesis b) 2-methoxy propane
d) Grignard's synthesis c) 2-methoxy propane
94. Ether is prepared by d) methoxy ethane
a) Williamson's synthesis 103. Two mole of alkyl iodide is formed when ether
b) Wurtz's reaction react with
c) Fridel-Craft's reaction a) Hot I2 b) Cold HI
d) Hoffman bromide reaction c) Cald I2 d) Hot HI

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104. C–O bond in ether is not cleaved by 114. An hypothetical compound does not react with
a) HCl b) Dil.H2SO4 sodium metal. Which type of compound behave
like this?
c) HBr d) HI
a) alcohol b) Phenols
105. Acidic hydrolysis of ether gives
c) Ethers d) Acid
a) Two mole of aldehyde
115. The ethers heated with excess of HI gives three
b) One mole of alcohol
different products. The ether wi11 be
c) One mole of aldehyde
a) simple
d) Two mole of alcohol
b) mixed
106. Reaction of dimethyl ether with cold HI is
c) ether simple or mixed
a) E2 reaction b) SN1 reaction
d) unpredictable in nature
c) E1 reaction d) SN2 reaction
116. The ompound which is mixed with alcohol to get
107. Molecular formula (A) C4H10 O on acid hydrolysis substitute for petrol is
gives two mole of same alcohol. The compound
a) ethanol b) diethyl ether
A is
c) acetaldehyde d) propanol
a) 2-methoxy propaneb) 1-methoxy propane
117. Dietyl ether does not react with
c) t-butyl alcohol d) Diethyl ether
a) dil.H2SO4 b) HI
108. Ethers are reacted with cold HI gives
c) H3COOH d) PC15
a) One mole alcohol and one mole of alkyl iodide
118. Find out major final product in the following
b) Two mole alcohol
reaction
c) Two mole of alkyl iodide
d) Two mole alcohol and one mole of alkyl iodide ONa

109. The reaction CH3OC2H5 with cold HI gives

+ Nitrating
a) CH3OH + C2H5I b) CH3I + C2H5OH (A)  B
mixture
Cl
c) CH3I + C2H5I d) CH3OH + C2H5OH
110. Diethyl ether on heating with conc. HI gives two O
moles of O

a) ethanol b) iodoform a) b) O N
2

c) ethyl iodide d) methyl iodide NO2

111. Natalite is a mixture of
a) diethyl ether and methanol O
b) diethyl ether and ethanol O

c) dimethyl ether and methanol c) d)

NO2
d) dimethyl ether and ethanol
112. Ethers are inactive because they do not contain NO 2
119. The ether
a) active atom b) active group
c) multiple bond d) all of these
O CH2
113. Diethyl ether with cold HI yields
a) C2H5I
when reacted with cold HI gives
b) C2H5OH a) mixture of 3 and 4
c) C2H5 I and C2H5OH b) mixture of 1 and 2
d) none of these c) mixture of 2 and 3
d) mixture of 1 and 4

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120. Diethyl ether can be regarded as unhydride of 127. Anisole is reacted with cold HI gives
a) CH3–OH b) C2H5–OH a) Benzyl iodide and methanol
c) C2H5–COOH d) CH3COOH b) Phenol and methanol
121. Dimethyl ether can be decomposed by heating c) Iodobenzene and iodomethane
with d) Phenol and iodomethane
a) H2O b) NaOH 128. Reaction of CH3OCH2CH3 is maximum with
c) KMnO4 d) HI a) HF b) HCl
122. The product (C) in the following reaction is c) HBr d) HI
OH 3 129. Ethyl phenyl ether on boiling with conc. HBr gives
Na C2 H 5 H 3O
  A   B  
a) phenol and ethane
b) bromobenzene and ethane
OH c) bromoebenzene and bromoethane
a) b)
d) phenol and bromoethane
OH
130. HI cleaves ether (A) formings
OH
c) d) A: CH2–O–CH3
OH

123. Following reaction is of the type

cold a) CH2OH1CH3I
R  O  R '  HBr   R  BR  R ' OH
If R' is 30 alkyl group and R is 10 alkyl group,
then
b) CH2ICH3I
a) SN1 with tertiary alkyl group
b) SN2 with primary alkyl group
c) both of the above types d) CH2I,CH3OH
d) none of the above types
124. The mixture of ethanol and H2SO4 is distilled in 131. Anisole on treatment with Br2/CS2 gives
distillation flask at 1400 C. The flask would then a) bromobenzene
contain
b) methyl 2-bromophenyl ether
a) H2SO4 and C2H5–O–C2H5 only
c) o nd p-bromoanisole
b) H2O, H2SO4 and C2H5OSO3H only
d) phenol
c) H2O, C2H2OSO3H, C2H5
132. Which of the following is not cleaved by HI even
d) C2H5–O–C2H5, C2H5OSO3H, H2SO4 and H2O
at 525 K
only
a) C6H5–O–CH3 b) CH3–O–C2H5
125. Methoxy ethane does not react with
c) C6H5–O–C3H7 d) C6H5–O–C6H5
a) HI b) HBr
133. Which is the most stable ion in he protonation of
c) dil.H2SO4 d) Na
126. Which of the following will not form ether? (CH3)3C–O–CH2CH3

a) R–X + C6H5ONa 

a) (CH 3 )3 C  O CH 2 CH 3
|
b) R  X 
moist Ag 2 O
H
c) R  X  R  ONa 
 b) (CH3)3C+
c) (CH3)–CH2+
HBF3
d) CH 2 N 2  R  OH 
 d) None of these

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134. Which of the following reaction is not possible
I
Na c) I and
a) C2 H5  O  C2 H5  

b) R  X  moist Ag 2 O 
 OH
d) OH and
conc. H 2SO4
c) C2 H5 OH 
453 K

139. Compound 'A' react with CH3–Cl gives B. B reacts
alc. KOH
d) C2 H 5  Cl   with dil. H 2 SO 4 gives ethyl alcohol and
CH3–OH. The compound A is
135. Meth1 phenyl ether can be obtained by reacting
a) C2H5–OH b) CH2 = CH2
a phenolate ions and methyl iodide
c) CH  CH d) C2H5–ONa
b) methoxide ion and bromobenzene
140. In which of the following reaction product is
c) ethanol and phenol t-butyl methyl ether
d) bromobenzene and methyl bromide conc. H 2SO4
a) C2 H5  OH  C2 H5  OH  
136. The major organic product in following reaction
is b) (CH 3 )3 C  Br  CH3ONa 


c) CH3  Br  (CH3 )3 C  ONa 


+ HI 
cold

O
d) (CH3 )3 C  Br  CH3  OH 

a) CH3I and 141. Which of the following compound when heated
OH
with HI gives two mole of different alkyl iodide?
a) C2H5–OH b) C2R5–O–C2H5
b) CH3–I and c) CH3–O–C2H5 d) CH3–O–CH3
OH 142. Which of the following will gives good yield of
ether?
c) CH3–OH and
I OH OCH3
(i) Na
a) 
(ii) CH 3  Br
d) CH3–OH and
I
OH OCH3
137. Formation ether from ethanol based on
(i) Na
a) dehydration b) hydrogenation b) 
(ii) CH 3  I

c) dehydrogenation d) hydration
138. In the reaction OH OCH3
(i) Na
c) 
(ii) CH 3  CI
O + 2HI 
 

which ofthe following compound will be formed? OH OCH3

(i) Na
OH d) 
(ii) CH 3  F
a) I and
143. Ethers can be prepared by
I 1) eating alkyl halide with R –OH
b) OH and 2) boiling alkyl halide with alc. KOH
3) heating alkyl halide with sodium alkoxide
4) reacting alcohol with diazomethane

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a) 2, 3, 4 b) 1, 2, 3 149. CH3–O–C(CH3)3 on reaction with dil. H2SO4
c) 3, 4 d) 1, 2 under pressure gives (A) and (B). These are
reacted with cold HI gives
144. Product of following reaction will be
The compound A and B are respectively
OH
Na n  prop  Br
a) (CH3)3C–I and CH3–I
  (A)   (B)
b) (CH3)sC–OH and CH3-I
c) (CH3)3C–I and CH3–OH
O d) (CH3)3C–OH and CH3–OH
O
a) b) 150. Conversion of alcohol to ether in the presence of
conc. H2SO4 is an example of
a) SN1 reaction b) SN2 reaction
O O c) El reaction d) E2 reaction
c) d)
CH 3
145. What is the function of diethyl ether in Grignards |
151. CH  C  CH can be prepared
reagent preparation 3 2

1) to act as a catalyst |
CH 3
2) to act as a solvent
3) to provide lone pair electron to co-ordination from Williamson reaction using
4) to act as an acid
a) 1, 2 b) 2, 3 Cl and ONa
a)
c) 3, 4 d) 2, 4
146. Phenetole react with cold HI gives
Cold
 gdfd
 
a) C2H5–I + C2H5–OH Cl and ONa
b)
b) C2H5–I + C6H5–OH
c) C6H5CH2–OH + C2H5–I
ONa
d) C6H5–OH + CH3–CH2–H2OH
147. Select the incorrect statement among the following c) Cl and
0
a) C–O–C bond angle in ether is 110
b) ethoxy ethane is reacted ith excess of HI gives d) Both (b) and (c)
ethyl iodide 152. Which of the following is not useful for the
c) ethers and alcohols are functional isomers synthesis of ether?
d) ethers are Lewis base hence do not react with
X
Bronsted acid like H2SO4
148. Which of the following statement about ethers is/ a) + R–ONa 

are incorrect?
1) Ethers are very reactive b) CH2N2 R–OH HBF
4 
2) Ethers are weakly acidic
ONa
3) Ethers are Lewis base
4) Ether form stable complex with Lewis acid c) R–X 

a) 1, 2, 3 b) 1, 2
c) 2, 3, 4 d) 2, 4 d) 2ROH Conc
 . H 2 SO4 / 413
 

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153. Product of following reaction is 157. Which one of the following is incorrect about
dimethyl ether?
O a) It has boiling point lower th alcohol
+ HI Cold
 b) It is symmetrical ether
c) It boiling point is more tha ethanol
d) On treating with hot HI give single product
I OH 158. Dieth1 ether finds its use in medicine as
a) and
a) anaesthetic b) antiseptic
c) hypnotic d) pain killer
I OH
159. Ethers form co-ordination complexes with
b) and a) BF3 b) AlCl3
c) ZnC12 d) all of these
I 160. Ethers on hydrolysis yield
I a) ketone b) acid
c) and
c) alcohol d) aldehyde
161. Ethers are basic in nature owing to the presence
OH
of
d) and OH
a) unshared electron pairs on oxygen
b) alkyl group
Hot
154. C4 H10 O  HI  R1  I  R 2  I c) turn blue litmus red
R1 – I and R2–1 on alkaline hydrolysis gives d) all of these
a1cohol A and B respectively. The compound A 162. Ethers with conc. HI at low temperature form
and gives haloform test. The original campounds a) alkyl iodide b) alcohol
is c) Both a and b d) oxonium salt
163. When ethyl isopropyl ether is reacted with HI in
a) b) O cold gives,
O a) C2H5I and (CH3)2CHOH
b) C2H5I and (CH3)2CHI
c) d) OH c) C2H5OH and (CH3)2CHI
O
d) C2H5OH and (CH3)2CHOH
155. Which of the following can no be made by 164. Some statements are given below about ethers,
Williason's reaction?
1. with strong acid, forms oxonium salt
a) ethoxy ethane
2. mixture of diethyl ether and ethanol called as
b) methoxy ethane natalite
c) l-methoxy propane 3. t-butyl halide and sodium ethoxide give ethyl
d) 2-(1, 1-dimethyl ethoxy) propane t-butyl ether
156. Some statements are given belov about ethers, 4. these are acids
(1) Oxygen atom is sp3-hydridised Among the above, false statement(s) is/are
(2) they are liquids at room temerature a) only 1 and 3 b) only 2 and 4
(3) they have higher boiling point than alcohols c) only 3 and 4 d) only 4
(4) they are very active 165. The compound that does not react with sodium is
a) only 1 b) only 3 and 4 a) CH 3 CH 3 b) CH 3COOH
c) only 1 and 2 d) all of these c) CH 3CHOHCH 3 d) C 2 H 5 OH

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166. Which of .the following ether will give two 174. Ethers are mainly used as,
successive members of homologous series, on a) solvent b) cooling agent
acid hydrolysis?
c) a aesthetic d) ubstitute of petrol
a) Diethyl ether b) Dimethyl ether
175. A temperature of –1100 C can be obtained by
c)Ethyl methyl d) Methyl n-propyl ether using
167. The reaction of ether with HI is preferred than a) ether and CO2 b) ether and solid CO2
HBr because
c) acetone and CO2 d) acetone and solid CO2
a) HI is a stronger acid than HBr
176. The cleavage of an ethyl methyl ether with cold
b) HI gives a higher concentration of oxonium
hydrogen iodide will give
ion
a) a molecule each of an methyl ipdide and water
c) I– is a better nucleophile in SN2 reaction than
the Br– ion b) a molecule each of an ethyl iodide and water
d) all of these c) a molecule each of ethanol and an methyl iodide
168. Find out process involved in the following reaction, d) a molecule each of an ethyl iodide, methyl
iodide and water.
dil. H 2SO 4
R  O  R  H 2 O 
under press
 ROH  ROH 177. Which of the following is a gas at room
a) hydrolysis b) oxidation temperature?
c) hydration d) reduction a) CH3CH3 b) HCHO
169. The central oxygen atom in ether is c) Both 'a' and 'b' d) CH 3OCH 3
a) sp2-hybridised b) sp3-hybridised 178. Some statements are given below about ethers,
c) sp-hybridised d) dsp2-hybridised (1) they are Lewis bases
170. Which of the following statements is false in case (2) their boiling point increases with increasing
of ethoxy ethane? molecular weight
a) It is inflammable. (3) all are volatile liquids at room temperature
b) It is simple ether. (4) with water dimethyl ether form hydrogen bond
c) It reacts with Na metal
d) It is used as anaesthetic. Among the above, false statement(s) is/are
171. Ether does not react with a) only 4 b) only 3 and 4
a) scdium metal c) only 3 d) none of these
b) sodium hydroxide dil. H2SO4
179. Ether  H2O
 two products
c) phosphorus trichloride
d) all of these One of the product on oxidation give acetic acid,
172. Isobutyl n-butyl ether is reacted with cold conc. while the other on oxidation give acetone. The
HI gives ether is,
a) CH3CH2CH2CH2I + (CH3)2CHCH2OH a) ethyl n-propyl ether
b) CH3CH2CH2CH2OH + (CH3)2CHCH2I b) ethyl methyl ether
c) CH3CH2CH2CH2I + (CH3)2CHCH2I c) ethyl isopropyl ether
d) CH3CH2CH2CH2OH + (CH3)2PHCH2OH d) methyl isopropyl ether
173. The rieaction of CH3OCH2CH3 with hot excess 180. Some statements are given below about diethyl
HI gives ether,
a) CH3OH + CH3CH2I (1) Its boiling point lower than I-butanol.
b) CH3I+ CH3CH2OH (2) It is used as anaesthetic.
c) CH3OH + CH3CH2OH (3) With dilute H2SO4 it give two homologue
d) CH3I + CH3CH2I (4) With cold HI give iodoethane

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Among the above, correct statement(s) is/are c) Perkin's reaction
a) only 1 b) only 1 and 2 d) Williamson's synthesis
c) only 2 d) only 1, 2 and 4 189. Consider the following reaction
181. The number of bond pair and lone pair on oxygen 
A  CH3ONa  cold HI
 B   C2 H5  OH
atom in ether are respectively
+ CH3–I
a) 1 and 2 b) 2 and 1
The compound A is
c) 2 and 2 d) 1 and 3
a) C2H5–OH b) C2H5–CHO
182. Diethy Iether can be decomposed by heating with
c) C2H5–Br d) C2H5
a) NaOH b) KMnO4 solution
190. Which one of the following statement is not true
c) water d) HI
a) These are Lewis bases.
183. Which of the following is most suitable reagent
to distinguish ether from alcohol ? b) They are highly inflammable.
a) Na metal b) HI c) They on acid hydrolysis gives alchohol.
c) HBr d) All of these d) These are Lewis acid.
184. Which of the following is used in the preparation 191. What are the product of following reaction ?
of RMgX ? cold HI
C2 H5 OCH3  
a) Dimethyl ether b) Diethyl ether
a) C2H5OH + CH3I
c) Ethyl methyl ether d) Ethanol
b) C2H5I + CH3OH
185. Which of the following give methyl alcohol with
c) C2H5OH + CH3OH
cold HBr
d) C2H5 I + CH3I
a) CH 3–O–CH 2–CH 2–CH 2–CH 3
192. IUPAC name of ethyl isopropyl ether
CH 3 a) 2-ethoxy propane
|
b) CH 3  O  C  CH 3 b) l-ethoxy propane
|
CH 3 c) 2-methy1 2-ethoxy propane
d) 1-methy1 2-ethoxy propane
CH3 193. Major product of following reaction is
|
c) CH3  O  CH 2  CH  CH3 O C 2H6
S2SO4
d) CH3  O  CH  CH 2  CH3 + HNO 3  
|
CH 3
186. On heating diethyl ether conc. HI, 2 moles of O C 2H 6 O C2 H6
which of the following is formed? NO2
a) Ethanol b) Iodoform a) b)
c) Ethyl iodide d) Methyl iodide NO2 NO2
187. By the action of CH3I on sodium ethoxide, we
get O C2H6 O C2H 6
a) CH 3COOCH 3 b) CH 3COC 2H 5 O 2N
c) CH 3OC 2H 5 d) Ethyl acetate
188. Ethyl chloride is converted into diethyl ether by c) d)
a) Wurtz synthesis
NO2 NO 2
b) Grignard reaction

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194. 4-alkoxy alkyl benzene is obtained from
a) Friedel-Craft reaction O
b) Ulmann reaction Cl
a) +
c) Wurtz-fitting reaction
O
d) Fitting reaction
195. Minor product obtained when anisole on O O
methylation
b)
+ Cl
O C2H 6 O CH3
O CH3 O Cl
a) b)
CH3 c) +
O

O CH3 O CH3 O O
CH 3 O
c) d) d) O
+

CH 3 199. Actually 18-crown- 6 ether means

a) 18-oxygen and 6 carbon
196. Acylation of alkyl phenyl ether gives
b) 12-carbon and 6-oxygen
a) 2-alkoxy alkyl phenyl ketone (major)
c) 12-carbon and 12-oxygen
b) 4-alkoxy alkyl phenyl ketone (minor)
d) 6-oxygen and 6-carbon
c) 4-alkoxy alkyl phenyl ketone (major)
200. 18-crown-6 ether is able to trap
d) 3-alkoxy alkyl phenyl ketone (major)
a) K+ b) Na+
197. Product of following reaction is
c) Li+ d) all of these
O 201. Whic crown ether is used to extract cerium?
+ (major) a) 15-crown-5 b) 18-crown-6
c) 12-crown-4 d) 10-crown-3
202. Dietyl ether is safe anesthtic agent. On
O
O administration it affect quick to the central nerve
system because
a) b)
O a) it is more soluble in fatty acid than water
b) it is more soluble in water t an fatty acid
c) it is not soluble in fatty acid
O
O d) it is highly inflammable
203. Which of the following is not used as anesthetic
c) d) O agent?
a) Diethyl ether b) Nitrous oxide
O
c) Haloethane d) Methanol
198. 4-methoxy-acetophenone is obtained from 204. Lower molecular weight optically active ether is
reacted with cold HI gives
a) butan-l-ol and iodomethane

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b) butan-2-ol and iodomethane
CH 3
c) propan-l-ol and iodoethane |
 NaCl
d) propan-2-ol and iodoethane CH 3  C  ONa  CH 3 CH 2  Cl  
|
205. Product of following reaction is CH 3

CH 3  CH  CH 2  O  C2 H 5  HBr  
| CH 3
OH |
CH 3  C  O  CH 2  CH 3
a) C2H5 Br and CH3CHBrCH3 |
CH 3
b) C2H5 Br and CH3CHBrCH2Br
c) C2H5 Br and CH3CHOHCH2Br a) Williamson's Synthesis
d) C2H5OH and CHBrCH2Br b) Williamson continous etherification process
206. The reaction c) Etard reaction
d) Gatterman-Koch reaction

1. (a) 2. (b) 3. (b) 4. (a) 5. (c) 6. (a) 7. (b) 8. (b) 9. (b) 10. (c)
11. (c) 12. (b) 13. (c) 14. (b) 15. (c) 16. (a) 17. (c) 18. (c) 19. (b) 20. (a)
21. (c) 22. (a) 23. (b) 24. (a) 25. (b) 26. (a) 27. (c) 28. (b) 29. (a) 30. (b)
31. (b) 32. (c) 33. (a) 34. (d) 35. (b) 36. (a) 37. (b) 38. (d) 39. (b) 40. (c)
41. (d) 42. (c) 43. (b) 44. (b) 45. (a) 46. (a) 47. (d) 48. (d) 49. (b) 50. (d)
51. (b) 52. (b) 53. (a) 54. (a) 55. (b) 56. (b) 57. (d) 58. (b) 59. (d) 60. (b)
61. (b) 62. (b) 63. (c) 64. (c) 65. (c) 66. (b) 67. (a) 68. (d) 69. (b) 70. (b)
71. (d) 72. (c) 73. (b) 74. (d) 75. (b) 76. (b) 77. (b) 78. (a) 79. (b) 80. (a)
81. (d) 82. (c) 83. (c) 84. (c) 85. (a) 86. (b) 87. (d) 88. (b) 89. (d) 90. (c)
91. (b) 92. (b) 93. (c) 94. (a) 95. (c) 96. (b) 97. (a) 98. (d) 99. (b) 100. (c)
101.(a) 102. (a) 103. (d) 104. (a) 105. (d) 106. (d) 107. (d) 108. (a) 109. (b) 110.(a)
111. (b) 112. (d) 113. (c) 114. (c) 115. (b) 116. (b) 117. (c) 118. (b) 119. (b) 120. (b)
121.(d) 122. (a) 123. (c) 124. (d) 125. (d) 126. (b) 127. (d) 128. (d) 129. (d) 130. (a)
131.(c) 132. (d) 133. (b) 134. (a) 135. (a) 136. (b) 137. (a) 138. (c) 139. (d) 140. (c)
141.(c) 142. (b) 143. (c) 144. (c) 145. (b) 146. (b) 147. (d) 148. (6) 149. (a) 150. (b)
151.(b) 152. (a) 153. (b) 154. (b) 155. (d) 156. (a) 157. (c) 158. (a) 159. (d) 160. (c)
161.(a) 162. (c) 163. (c) 164. (c) 165. (a) 166. (c) 167. (d) 168. (a) 169. (b) 170. (c)
171.(d) 172. (b) 173. (d) 174. (a) 175. (b) 176. (c) 177. (c) 178. (c) 179. (c) 180. (b)
181.(c) 182. (d) 183. (a) 184. (b) 185. (b) 186. (c) 187. (c) 188. (d) 189. (c) 190. (d)
191.(a) 192. (a) 193. (c) 194. (a) 195. (c) 196. (c) 197. (d) 198. (c) 199. (b) 200. (a)
201.(b) 202. (a) 203. (d) 204. (b) 205. (b) 206. (a)

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Objective Type Questions
Section III : Phenols 9. When bromine is dissolved in CS2 and treated
1. In industry phenol is prepared from with phenol gives major product
1. Raschig's method a) 0-promophenol
2. Oxidation of cumene b) p-romophenol
3. Dow's method c) mixture of 'a' and 'b'
4. Oxidation of hexane d) 2, 4, 6-tribromophenol
a) 1,2 b) 2, 3 10. Kolbe s-Schmidt reaction is used 0 prepare
c) 3, 4 d) 1, 2, 3 a) salicylic acid b) salicylaldehyde
2. Replacement of N2+X– can be done by c) phenyl acetate d) o-xylene
a) H3O+ b) aq.NaOH 12. Product of following reaction is
c) alc.KOB d) moist Ag2O OH
3. Carbolic acid is obtained from oxidation of (i ) NaOH
 
(ii)CO / H 
2
a) sodium salicylate b) salicylic acid
c) toluene d) cumene a) 2- hydroxy benzoic acid
4. Cumene on air oxidation give b) 2-hydroxy benzaldehyde
a) carbonic acid b) carbolic acid c) sodium benzoate
c) caboxylic acid d) oxalic acid d) sodium phenoxide
5. Phenol reacts with NaOH and followed by 13. Product of the following reaction is
treatment with CH3  X gives
a) phenetole b) phenyl acetate OH
(i) CHCl3

(ii) NaOH

c) anisole d) toluene (iii) H 
6. Select incorrect statement
a) Reaction with Br 2 and water gives 2, 4, a) 2-1 ydroxy benzaldehyde
6-tribromo phenol b) 2-1 ydroxy benzoic acid
b) Reaction with dilute HNO3 gives mixture of c) benazoic acid
o-nitrophenol (minor) and p-nitrophenol (major). d) be rzaldehyde
c) Reaction with nitrating mixture gives picric 14. Benzene diazonium chloride is onverted into
acid. pheno by
d) Reaction with cone. H2SO4 at 300 K gives a) oxidation b) reduction
o-phenol sulphonic acid
c) neutralisation d) hydrolysis
7. Consider the following species
15. Cresols have
(1) o-nitrophenol
a) 2-OH groups
(2) p-nitrophenol
b) 4-OH groups
(3) o-bromo phenol
c) 1-OH group
Intramolecular hydrogen bonding can takes place
d) 5-OB groups
in
16. Find out A in the following reaction
a) only 3 b) 1 and 3
c) only 1 d) 2 and 3 OH
8. Which is steam volatile?
c) o-nitrophenol b) m-nitrophenol + 3Br2 
Water
 A + 3 HBr..
c) p-nitrophenol d) picric acid

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The compound A is 23. Find out 'B' in the following reaction
a) o-bromo phenol
Cl
b) 2,4,6-tribromo phenol
c) p-bromo phenol + H2O  conc.H 2SO4
SiO 2
 A 
R.T.
B
d) m-bromo phenol
17. Benzene suiphonic acid is reacted with NaOH
gives
OH
a) sodium phenoxide
SO 3H
b) cumene
c) cumene hydroperoxide
a) b)
d) sodium benzene sulphonate
18. Product obtained when steam is passed over SO 3H
chlorobenzene
a) sodium phenoxide SO 3H OH
b) sodium benzene sulphonate SO3H OSO3H
c) carbolic acid c) d)
d) benzene diazonium salt
19. Find out A and B in the following reaction
24. Which of the following is /are steam volatile?
respectively
1) p-bnitrophenol
Ph–Cl 
A
 Ph-ONa 
B
 Ph–OH 2) o-nitrophenol
a) NaOH and HCI b) H2O and HCI 3) o-hydroxy acetophenon
c) HCI and NaOH d) HCI and H2O 4) p-hydroxy acetophenone
20. Phenol is a) 1,4 b) 2,3
a) neutral b) amphoteric c) 1,2 d) 3,4
c) basic d) acidic 25. The formation of salicylic acid from phenol using
21. Phenol on oxidation by chromic acid gives NaOH and CO2 is known as
a) Friedel-Craft reaction
O b) Kolbe's Schmidt reaction
O
c) Reimeter and Tiemann reaction
O
a) b) d) Fitting reaction
Zn Conc. HNO3
26. Phenol 

 (A) 
conc. H 2SO4 at 270 C
 (B)
O
Fe  HCl
 (C)
O 27. In diazotisation reaction, carbolic acid is prepared
O
from
a) cumene b) chloro enzene
c) d)
c) anilne d) sod. phenoxide
O O 28. Cumene is converted in phenol by
a) reduction and decomposit on by acid
22. P-benzoquinone is obtained from phenol by
b) oxidation and decomposition by acid
a) reduction b) oxidation
c) reduction and decomposit on by alkali
c) acidic hydrolysis d) alkaline hydrolysis
d) oxidation and decompositi on by alkali

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29. Phenol on standing in air develop a red colour, 38. Picric acid contain
due to formation of a) 2-nitro groups b) 3-nitro groups
a) cyclohexane b) phenoquinone c) 2-nitrite groups d) 3-nitrite groups
c) resorcinol d) quinol 39. Phenol is
30. Bnzene is obtained from phenol by using a) a base weaker than ammonia
a) Na metal b) Ca metal b) an acid stronger than carboxylic acid
c) Zn metal d) NaOH c) an acid weaker than carboxylic acid
31. Benzene phenol is reacted with CHCl3 and NaOH, d) a neutral compound.
followed by treatment with LiAIH4 gives
40. The synthesis of PhOH from PhCl is called
a) m-hydroxy benzyl alcohol
a) Cumene process
b) p-hydroxy benzyl alcohol
b) Dow's process
c) o-hydroxy benzyl alcohol:
c) Williamson's syntnesis
d) o-hydroxy benzyaldehyde,
d) Wurtz synthesis
32. Reagent used in Reimer - Tiemann reaction are
41. Pheno reacts with bromine in CS 2 at low
a) CH3Cl and aq.NaOH temperature to give
b) CH3Cl and POC3 a) m- romophenol
C) CHCl3 and aq. NaOR b) p-b omophenol
d) CHCl3 and ale. NaOH c) o and p-bromophenols
33. Ka value of phenol d) 2,4, 6-tribromophenol
a) More than carboxylic acid 42. When henol is treated with ex ess brominewater,
b) Less than alcohol it gives
c) More than alcohol a) m- romophenol
d) Less than water b) 0 and p-bromophenols
34. Salicylic acid is prepared from phenol by the c) 2, -dibrornophenol
reaction known as d) 2, 4, 6-tribromophenol
a) Wurtz reaction 43. Which of the following reagents c nnot be used to
b) Williamson reaction distinguish between phenol an alcohol?
c) Kolbes-Schmidt reaction a) Br2/CCl4 b) NaOH
d) esterification c) NaHCO3 d) neutral FeC3
35. C–O bond length in phenol is less than C–O length 44. An organic compound with mole ular formula
in methyl alcohol because C6H-dissolves in NaOR and gives characteristics
a) partial double bond character due to resonance colour with neut al FeCI3. On treatement with
bromine water, it gives tempeature to give tribromo
b) partial double bond character due to inductive
derivative. The compound is
effect
a) alcohols b) ketones
c) more electronegativity of oxygen
c) ethers d) phenol
d) oxygen contain two lone pair of electrons
45. In the nitration of phenol with a mixture of cone.
36. The most suitable method of separation of ortho
HNO3 and conc. H2SO4, the a active species
and para-nitrophenol mixed in the ratio of 1 : 1 is
involved is
a) stem distillation b) vapourisation
a) nitronium ion
c) crystallisation d) colour spectrum
b) nitrogen peroxide
37. The reaction of phenol with air.The product is
c) nitrogen peroxide
a) Anthraquinone b) Benzophenone
d) nitrogen peroxide
c) Benzoquinone d) Propiophenone

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46. Carbolic acid is 56. Which of the following is explosive?
a) C6H5CRO b) C6R6 a) Picric acid b) Methyl amine
c) C6H5COOR c) C6H5OR c) Cumene d) Ethanol
47. Under different conditions nitra ion of phenol 57. Nitrating mixture consist of
yields
a) cone. HNO3 + conc. HCI
a) o-nitrophenol b) p- itrophenol
b) conc. HNO3 + conc. H2SO4
c) 2, 4,6-trinitro phenol d) all of these
48. Picric acid is 58. cone. H2SO4 + cone. H3PO4
a) a volatile liquid a) phenyl n-propane
b) trinitroaniline b) 2-propyl benzene
c) 2, 4, 6-trinitrophenol c) chlorobenzene
d) butyric acid d) benzene
49. The end product in the following reaction is, 59. Sodium salt of benzene sulpho ic acid on fusion
PhCI  A  B
H 2O  CuC2 Conc.HNO3 caustic soda and followed y treatment with gives
a) PhOH b) PhBr a) acetic acid b) cumen
c) PhNO2 d) Picric acid c) phenol d) picric acid
50. Phenol is heated with conc.H 2 SO 4 at high 60. Nitration of phenol is
temperature gives, a) nucleophilic substitution
a) o-phenol sulphonic acid b) electrophilic substitution
b) p-phenol sulphonic acid
c) elemination
c) m-phenol sulphonic acid
d) none of these
d) all of these
61. 01 is ortho and para directi g due to electron ensity
51. Phenol gives violet colour with
increases
a) neutral FeCl3 b) neutral FeSO4
a) ortho position b) para position
c) acidic FeCl3 d) acidic FeSO4
52. Picric acid is obtained by the nitration of c) meta position d) both 'a' and 'b'
a) cumene b) phenol 62. 4-bromophenol is mainly form d, when phenol is
c) methanol d) ethanol is reacted with,
53. Acidic nature of phenol is due to a) Br/water b) Br2/line solvent
a) phenolic group c) HBr/water d) HBr/inert solvent
b) benzene group 63. The number of (J and n-bond present in the
c) hydrogen bonding molecule of carbolic acid are respectively
d) resonance stabilisation of phenoxide ion a) 7,3 b) 2, 3
54. Carbolic acid is reacted with cone.H2SO4 at 300K c) 4, 3 d) 13,3
gives, 64. During preparation of phenol from cumene, side
a) 2-phenol suiphonic acid product obtained is
b) 3-phenol sulphonic acid a) cetone b) alcohol
c) 4-phenol sulphonic acid c) aldehyde d) acid
d) 2 and 4-phenol sulphonic acid
65. Sulphonation of phenol with cone. H2SO4 at 288
55. Phenol reacts with Br2 in CC14 at lowtemperature 293 K gives
to give
a) -phenol sulphuric acid
a) o-and p-bromophenol
b) -phenol sulphonic acid
b) m-bromophenol
c) p-bromophenol c) -phenol sulphonic acid
d) 2, 4, 6-tribuomophenol d) all of these

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c) the introduction of –SO2H group in benzene
66. CH(CH3)2 
 OH d) all of these
73. At different condition nitration of phenol gives
This change can be carried out by using a) O-nitrophenol b) p-nitrophenol
a) reduction c) picric acid d) all of these
b) nascent oxygen 74. How many O-H groups are, present in
c) air oxidation phloroglucinol?
d) hydrolysis a) 3 b) 2
c) 4 d) 5
67. Cl 
A
 OH A can be 75. Diazotis tion reaction is used to prepare
a) alcohol b) phenol
a) SiO2 b) SiO2/steam
c) aldehyde d) ketone
c) steam d) aq. KOH
76. The reaction of cone. HNO3 and ph
68. For preparing monohalogen derivative of phenol,
a) benzoic acid b) salicylic acid
halogenation is carried out
c) 0- and p-nitrophenol d) pieri acid
a) at high temperature
77. At low emperature phenol reacts with Br2 in CS2
b) at low temperature
to form
c) in presence of non-polar solvents
a) m-bnomophenol
d) both 'b' and 'c'
b) 0- and p-bromophenol
69. 2-propyl benzene on air oxidation and followed
c) p-br mophenol
by decomposition by dilute acid gives
d) 2, 4, 6-tribromophenol
a) phenol and propanal
78. Picric acid is
b) phenol and propanone
a) trinitroaniline b) trinitrotol
c) phenol and propanol
c) p-bromophenol d) 2,4, 6-trini rotoluene
d) phenol and propionic acid
79. Chlorobenzene on fusing with solid NaOH gives
70. The reaction
a) benzoic b) benzoic acid
Ph–OH + dilute HNO3  ?
c) phenol d) benzyl chloride
Gives predominately
80. Bakelite plastic is formed, when phenol reacts with
a) 2-nitrocarbolic acid
a) CH3CHO b) HCHO
b) 4-nitrocarbolic acid
c) acetone d) HCOOH
c) 2-4-6 trinitro-carbolic acid
81. Aroma ic primary amine when treated with cold
d) 3-nitro carbolic acid HNO2 and HCl forms
71. Some statements are give below about, carbolic a) m-bromophenol
acid
b) 2-4, dibromophenol
1. it react with Na metal
c) 2,4, 6-tribromophenol
2. it gives violet colour with neutral FeC13
d) a mixture of 0-and p-bromophenols
3. it forms only one monobrominated product
82. Phenol is treated with bromin water and phenoxide
4. it is acidic in nature. ion?
a) only 4 b) only 2 and 4 a) m-dibromophenol
c) only 1, 2 and 4 d) all of these b) 2-4 dibromophenol
72. During sul phonation cone. H2S04 is used for c) 2, 4, 6-tribromophenol
a) the introduction of –SO3H group in benzene d) a ixture of 0- and p-bromoph nols
b) the introduction of –SO4H group in benzene

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83. The bakelite is prepared by the rea tion between 4. Intermolecular R-bonding is present in phenol
a) urea and formaldehyde a) 1, 3 b) 1, 2
b) ethylene glycol c) 3, 4 d) 1, 2, 3, 4
c) phenol and formaldehyde 88. Phenol is
d) tetramethylene amethylene glycol a) strong acidic b) weak acidic
84. Phenols are more acidic than aliphatic alcohols c) strong basic d) neutral
because 89. Which of the following group stabil iso the
a) phenoxide ion is stabilised by resonance phenoxide ion ?
b) phenols are more solubleinp lar solvents c) CR3 b) OR
c) phenoxide ion do not have re onance c) OR d) NO2
d) alcohols do not loose H-atom tall . 90. Which of the following group destabalise the
85. Which of the following is explosive? phenoxide ion
c) NO2 b) –CRO
OH c) COR d) OR
O 3N NO3
91. Which of the following is more acidic in nature
a)
OH
OH
NO3
1. 2.
OH NO2
O 3N NO3
b) OH
OH
NO2 NO2
3. 4.
O 3N NO3
NO2
c)
a) 1 > 2> 3> 4 b) 4 > 3> 2 > 1
NO2
c) 4 > 2> 3> 1 d) 4 > 1> 2 > 3
d) None of these 92. Which of the following is more acidic in nature?
Acidic Nature
86. Phenol is less acidic than OH OH
a) p-nitro phenol NO2
b) cresol
a) b)
c) ethanol
d) benzyl alcohol NO2 NO2
87. Which of the following statement is correct ?
1. electron withdrawing groups stabilize the OH
phenoxide ion and increase the acidic strength OH
O 3N NO3
2. electron donating groups destabilise the
phenoxide ion and decrease the acidic strength c) d)
3. -OR group in phenol is ortho and para directing. NO2

CHEMISTRY - XII OBJECTIVE

DGT Group - Tuitions (Feed Concepts) XIth – XIIth | JEE | CET | NEET | Call : 9920154035 / 8169861448
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Alcohols, Phenols and Ethers 47

93. Which of the following has more pKa value?
OH OH
OH OH
NO2
a) b) c) d)

CH2–CH 2–CH 3 C(CH3)3

OH OH
97. Decreasing order of acidity of substituted phenol
CN COOH is
c) d)
OH OH

94. Which of the following has more Ka value ?

1. 2.
OH OH
OCH3 NH2
O CH3
a) b)
OH OH
OCH3
3. 4.
OH OH
COOH Cl
c) d)
OH

95. Decreasing order of acidic nature of following

compound is 5.
OH OH OCH3
NO2
a) b) a) 3 > 1 > 4 > 5 > 2 b) 5 > 4> 3 > 1> 2
c) 5 > 4 > 3 > 2 > 1 d) 3 > 1 > 2 > 5 > 4
98. In which following first is more acidic than second?
OH
OH OH OH
OCH3
a) >
c) d)
OH OH OCH3

a) 1> 2 > 4> 3 b) 1> 4 > 3 > 2

OH OH
c) 2 > 1 > 3 > 4 d) 2 > 4 > 3 > 1
NO2
96. Which of the following is lowest Ka value? >

OH OH b)

NO2

a) b)

CH3 CH(CH3)2

CHEMISTRY - XII OBJECTIVE

DGT Group - Tuitions (Feed Concepts) XIth – XIIth | JEE | CET | NEET | Call : 9920154035 / 8169861448
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Alcohols, Phenols and Ethers 48

OH OH OH OH
NO2
>
c) a) b)
NO2 F OH

OH OH OH
OH
>
d) c) d)
NO2 CH3
NO2
102. Which of the following is less acidic?
99. Which of the following is most acidic ?
OH OH
OH COOH
CH 3
a) b)
a) b)

SO3H CH2OH OH
OH

c) d)
c) d)
NO2
100. In the following compound order acidity NO2

OH 103. Which of the anion is most stable due to

CH2OH delocalisation?
– –
O O
1. b. NO2
CH3 a) b)

OH OH
O O
–

3. 4. c) d)
NO3 NO2
NO2
104. Which is the correct decreasing order of acidic
a) 4 > 2 > 3 > 1 b) 4 > 3 > 1 2 strength of substituted phenol?
c) 4 > 3 > 2 > 1 d) 4 > 1> 2 3
OH OH
101. Which of the following is most acidic?
I I I
1. 2.
I

CHEMISTRY - XII OBJECTIVE

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Alcohols, Phenols and Ethers 49

107 Correct order of acidity of halogeneted phenol is
OH where X–F, Cl, Br, I
OH
OH OH
X
3. 4.
I 1. 2.
I I
I

a) 1 > 3 > 2 > 4 b) 3 > 1 > 2 > 4

OH
c) 1 > 4 > 2 > 3 d) 3 > 2 > 4 > 1 OH
105. The correct acidic strength order of phenol is

OH 3. 4.
OH X
X
Cl
1. 2. a) 1 > 2 > 3 > 4 > b) 4 > 3 > 2 > 1
c) 2 > 3 > 4 > 1 d) 2 > 4 > 3 > 1
CH3
108. Which of the following is more acidic?

OH OH OH
OH NH2 F
a) b)
3. 4.

NO2 Cl OH OH
NO2 Cl
a) 1 > 2 > 4 > 3 b) 3 > 1 > 4 > 2
c) d)
c) 1 > 2 > 3 > 4 d) 3 > 1 > 2 > 4
106. Correct order of acidic nature is
109. In which of the following first is more acidic than
OH OH second?
NH2
1. 2. OH OH
NO2
>
a)
OH NO2
OH
NO2

3. 4. OH OH
CH3 CH3
b) >
a) 1 > 3 > 2 > 4
CH3
b) 3 > 1 > 4 > 2
c) 3 > 4 > 2 > 1
d) 3 > 1 > 2 > 4

CHEMISTRY - XII OBJECTIVE

DGT Group - Tuitions (Feed Concepts) XIth – XIIth | JEE | CET | NEET | Call : 9920154035 / 8169861448
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Alcohols, Phenols and Ethers 50

110. Which of the following is less acidic in nature
OH OH
NH 2 OH
c) > OH
F
a) b)
OH OH
F
I
d) > OH OH

I c) d)
F

1. (d) 2. (a) 3. (d) 4. (b) 5. (c) 6. (b) 7. (c) 8. (a) 9. (b) 10. (a)
11. (b) 12. (a) 13. (a) 14. (d) 15. (c) 16. (b) 17. (d) 18. (c) 19. (a) 20. (d)
21. (a) 22. (b) 23. (c) 24. (b) 25. (b) 26. (d) 27. (c) 28. (b) 29. (b) 30. (c)
31. (c) 32. (e) 33. (c) 34. (c) 35. (a) 36. (a) 37. (c) 38. (b) 39. (c) 40. (b)
41. (c) 42. (d) 43. (c) 44. (d) 45. (b) 46. (d) 47. (d) 48. (c) 49. (d) 50. (b)
51. (a) 52. (b) 53. (d) 54. (a) 55. (a) 56. (a) 57. (b) 58. (b) 59. (c) 60. (b)
61. (d) 62. (b) 63. (d) 64. (a) 65. (a) 66. (c) 67. (b) 68. (d) 69. (b) 70. (a)
71. (c) 72. (a) 73. (d) 74. (a) 75. (b) 76. (d) 77. (b) 78. (d) 79. (c) 80. (b)
81. (b) 82. (c) 83. (c) 84. (a) 85. (b) 86. (a) 87. (d) 88. (b) 89. (d) 90. (d)
91. (b) 92. (c) 93. (a) 94. (c) 95. (c) 96. (d) 97. (a) 98. (d) 99. (c) 100. (b)
101. (a) 102. (b) 103. (b) 104. (c) 105. (b) 106. (c) 107. (c) 108. (c) 109. (b) 110. (a)

CHEMISTRY - XII OBJECTIVE

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DGT Group - Tuitions (Feed Concepts) XIth – XIIth | JEE | CET | NEET | Call : 9920154035 / 8169861448
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DGT Group - Tuitions (Feed Concepts) XIth – XIIth | JEE | CET | NEET | Call : 9920154035 / 8169861448
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DGT Group - Tuitions (Feed Concepts) XIth – XIIth | JEE | CET | NEET | Call : 9920154035 / 8169861448
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DGT Group - Tuitions (Feed Concepts) XIth – XIIth | JEE | CET | NEET | Call : 9920154035 / 8169861448
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DGT Group - Tuitions (Feed Concepts) XIth – XIIth | JEE | CET | NEET | Call : 9920154035 / 8169861448