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MOST EXPECTED QUESTIONS WITH ANSWERS CH.7 ALCOHOL,PHENOLS AND ETHER

BY: AMRITA SINGH

Directions: These questions consist of two statements, each printed as Assertion and Reason. While answering
these questions, you are required to choose any one of the following four responses.
(a) If both Assertion and Reason are correct and the Reason is a correct explanation of the Assertion.
(b) If both Assertion and Reason are correct but Reason is not a correct explanation of the Assertion.
(c) If the Assertion is correct but Reason is incorrect.
(d) If Assertion is incorrect and Reason are correct.

Q.1. Assertion : The boiling point of ethanol ius lower than that of diethyl ether.
Reason : In ethanol the molecules are associated due to inter molecular H-bonding.

Q.2. Assertion : Phenol gives 2,4.6-trinitrophenol on treatment with conc. HNO3.

Reason : -OH group in phenol is m-directing.

Q.3. Assertion : p-nitro phenol is more acidic than phenol.

Reason : Nitro group stablises the p-nitrophenoxide ion due to –I effect.

Q.4. Assertion : O-nitrophenol is more acidic than phenol.

Reason : Nitro group is electron donating group and therefore stabilizes ortho nitrophenoxide ion.

Q.5. Assertion : The C-O-C bond angle in ether is slightly less than tetrahedral angle.
Reason : Due to repulsive interaction between the two alkyl groups in ether.

Q.6. Assertion : Ortho and para- nitrophenols can be separated by steam distillation.
Reason : Ortho isomer associates through intermolecular hydrogen bonding while Para isomer associated
through intermolecular hydrogen bonding.

Q.7. Assertion : (CH3)3 CO-CH3 gives( CH3)3 C-I and CH3OH on treatment with HI.
Reason : The reaction occurs by SN1 mechanism.

Q.8. Assertion : o-nitrophenol is weaker acid than p- nitrophenol.

Reason : Intra molecular H-bonding makes ortho isomer weaker than para- isomer.

Q.9. Assertion : The C-O-H bond angle in alcohols is slightly less than the tetrahedral angle.
Reason : this is due to the repulsive interaction between the two lone pair of electrons on oxygen .

Q.10. Assertion : Phenol is more acidic than p-methyl phenol.

Reason : the presence of an electron releasing group in p-methyl phenol makes it less acidic.

Q.11. Assertion : P-nitrophenol is a stronger acid than p-cresol.

Reason : Nitro group is electron releasing while –CH3 group is electron withdrawing in nature.

Q.12. Assertion : Phenol do not react with phosphorous halide while alcohol do react.
Reason : In phenol C-O bond has partial double bond character due to resonance while it is not so in alcohols.

Q.13. Assertion : Alcohol have higher boiling point than alkanes of comparable molecular mass .
Reason : Alcohols have intra molecular hydrogen bond.

Q.14.Assertion: Tertiary alcohols get converted into an alkene instead of a carbonyl Compounds in the presence of
heated metallic copper.
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Reason: Tertiary alcohols prefer to undergo dehydrogenation instead of dehydration in the presence of heated
copper

Q.15 Assertion: Ethers are non-polar when they are symmetrical.

Reason: Ethers have a bent structure .

Q.16. Assertion: n-Butanol has higher boiling point than 2-methyl propan-2-ol.
Reason: Branching increases the strength of Vander Waals forces

Q.17. Assertion: It is not possible to prepare anisole from chlorobenzene through Willamson’s synthesis.
Reason: The C-Cl bond in chlorobenzene shows partial double bond character due to resonance.

Q.18. Assertion: Phenol on reaction with aqueous NaOH gives sodium phenoxide.
Reason: The reaction supports the acidic nature of phenol.

Q.19. Assertion: Boiling point of butan-1-ol is higher than that of butane-1-amine.

Reason: being more polar , butane-1-ol forms stronger intermolecular hydrogen bonds as compared to butane-1-
amine.

Answers: 1.(d), 2. (c), 3. (a),4. (c) , 5. (d), 6. (c), 7. (a),8. (a), 9. (a), 10. (a),11. (c), 12.(a), 13. (c)

14.(c),15.(d), 16.(c), 17. (a), 18.(a), 19. (a)

Q. (a). Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular
masses. Explain this fact.
( b). Which of the following isomers is more volatile: o-nitrophenol or p-nitrophenol?
Ans: (a). Alcohols can form H-bonds with water and break the H-bonds already existing between water molecules.
Therefore, they are in general, soluble in water. On the other hand, hydrocarbons cannot from H-bonds with water
and hence are insoluble in water.
(b). o-nitrophenol is more volatile due to intramolecular H-bonding.

Q.( a). Arrange the given compounds in the increasing order of acidity: Phenol, o-nitrophenol and o-Cresol.

(b). Alcohols react with active metals like Na, K.. to give corresponding alkoxide. Write down the
decreasing order of reactivity of sodium metal towards primary, secondary and tertiary alcohols ?
Ans: (a). o-Cresol < Phenol < o-Nitrophenol ( b). Primary >Secondary > Tertiary

Q.Which of the following will have a higher boiling point and why: CH3NH2 or CH3OH?
Ans: CH3OH will have a higher boiling point than CH3NH2. This can be explained as follows. Oxygen is more
electronegative than nitrogen and atomic size of oxygen is less than that of nitrogen. As such, the intermolecular
forces in CH3OH are stronger than in CH3NH2. Therefore, boiling point of CH3OH will be more than CH3NH2.

Q. Why primary alcohols are more acidic than secondary alcohol?

Ans. As we move from primary to secondary alcohol, the number of alkyl groups attached to the carbon having the
–OH group increases. Due to +I effect of alkyl group, the electron density on oxygen will be more in case of 2o
alcohols than in case of 1o alcohol. Hence the shared pair of electron of the O-H bond will be more displaced
towards the O atom in case of 1o alcohol than in case of 2o alcohol. Thus the release of proton (H+ ) is easier in case
of 1o alcohols than in case of 2o alcohol. Therefore, 1o alcohol is more acidic than 2o alcohol.

Q. a. Explain why phenols do not undergo substitution of the -OH group like alcohols?
b. Explain why nucleophilic substitution reactions are not very common in phenols?
c. Write the IUPAC names of CH3 CH=CH-CH2OH?
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Ans: (a) The C-O bond in phenols has some double bond character due to resonance and hence cannot be easily
cleaved by a nucleophile. In contrast, the C-O bond in alcohols is a pure single bond and hence can be easily cleaved
by a nucleophile.
(b). In phenols, the –OH group is an activating group. It activates the ring particularly at the ortho and para
positions due to greater electron density because of resonance. Hence ring responds to electrophilic substitution
and not nucleophilic substitution.
(c). But-2-en-1-ol

Q. . Explain why is ortho-nitrophenol more acidic than ortho-methoxyphenol ? b). Write the product
formed when Ethoxy benzene reacts with HI c). What is the condition of the compound to undergo
Iodoform test ?
Ans: ( a). Due to strong –R and –I-effect of the NO2 group, electron density in the O-H bond decreases and hence
the loss of a proton becomes easy. Further, after the loss of a proton, the-nitro phenoxide ion left behind is
stabilized by resonance, thereby making o-nitrophenol a stronger acid. In contrast, due to +R effect of the OCH3
group, the electron density in the O-H bond increases thereby making the loss of a proton difficult. Furthermore,
the o-methoxy phenoxide ion left after the loss of a proton is destabilized by resonance Because the two negative
repel each other thereby making o-methoxyphenol a weaker acid. Thus, o-nitrophenol is more acidic than o-
methoxyphenol.
(b). Phenol and Ethyl Iodide
( c). Presence of terminal methyl group with alcoholic / carbonylgroup [CH3C=O, CH3CH(OH) .

Q. Why is the reactivity of all the three classes of alcohols with conc. HCl and ZnCl2 (Lucas reagent)
different?
Ans: The reaction of alcohols with conc. HCl and ZnCl2 (Lucas reagent) occurs through intermediate formation of
carbocations. Obviously, more stable the carbocation, more reactive is the alcohol. Since the stability of
carbocations follows the order: 3° > 2° >10 , therefore, reactivity of alcohols towards Lucas reagent follows the
same order, i.e. , 3° > 2° > 1°.

Q. Give a chemical test to distinguish between 2-Pentanol and 3-Pentanol.

Ans. 2-pentanol gives Iodoform test with yellow ppt. of Iodoform while 3-pentanol does not give
this test.

Q.How would you obtain ethane-1, 2-diol from ethanol?

Ans.

Q.How would you obtain acetophenone from phenol?

Ans.
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QHow would you obtain phenol from benzene?

Ans.

Q.What happens when phenol is oxidized by Na2Cr2O7/H2SO4?

Ans.Phenol forms benzoquinone on oxidation with Na2Cr2O7 / H2SO4,

Q.What happens when phenol is heated with zinc dust?

Ans.
Benzene is formed when phenol is heated with zinc dust.

Q. What happens when phenol is treated with bromine water?

Ans. 2, 4, 6-tribromophenol is formed when phenol is treated with bromine water.

Q. Give simple chemical tests to distinguish between the following pairs of compounds: Benzoic acid and
Phenol
Ans. Ferric chloride test. Add neutral FeCl3 in both the solutions, phenol reacts with neutral FeCl3 to form an iron-
phenol complex giving violet colour but benzoic acid does not.

Q. Complete the following reaction equations :

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Ans.

Q. Write the final product(s) in each of the following reactions:

Q. Illustrate the following reactions giving a chemical equation for each :

(i) Kolbe’s reaction
(ii) Williamsons synthesis of an ether
Ans. (i) Kolbe’s reaction : Phenol reacts with CO2 in presence of sodium hydroxide (NaOH) at 4 – 7 Atm and 390 –
410 K giving salicylic acid
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(ii) Williamsons synthesis of an ether : The reaction involves the nucleophilic substitution of the halide ion from
the alkyl halide by the alkoxide ion by SN2 mechanism.
Example :

Q.Explain the following reactions with an example for each :

(i) Reimer-Tiemann reaction
(ii) Friedel-Crafts reaction
Answer:
(i) Reimer-Tiemann reaction : Treatment of phenol with CHCl3 in presence of aqueous NaOH at 340K followed by
hydrolysis gives salicylaldehyde.

(ii) Friedel-Crafts reaction : This reaction is used for introducing an alkyl or an acyl group into an aromatic
compound in presence of Lewis acid catalyst (AlCl3)
Example:

Q.How are the following conversions carried out?

(i) Propene to propan-2-ol
(ii) Ethylmagnesium chloride to propan-1-ol
Ans.
(i) Propene to propan-2-ol
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(ii) Ethylmagnesium chloride to propan-1-ol

Q.How are the following conversions carried out?

(i) Benzyl chloride to benzyl alcohol,
(ii) Methyl magnesium bromide to 2-methylpropan-2-ol.
Ans. (i) Benzyl chloride to benzyl alcohol

Q.Explain the following giving one example for each :

(i) Reimer-Tiemann reaction.
(ii) Friedel-Craft’s acetylation of anisole.
Answer:
(i) Reimer-Tiemann reaction : Treatment of phenol with CHCl3 in presence of aqueous NaOH at 340K followed by
hydrolysis gives salicylaldehyde.

(ii) Friedel-Craft’s acetylation of anisole :

Q.How would you obtain

(i) Picric acid (2, 4, 6-trinitrophenol) from phenol,
(ii) 2-Methylpropene from 2-methylpropanol?
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Ans. (i) Picric acid from phenol :

Q. Explain the mechanism of acid catalysed hydration of an alkene to form corresponding alcohol.
Ans. Acid catalysed hydration : Alkenes react with water in the presence of acid as catalyst to form alcohols

Mechanism : It involves three steps :

(i) Protonation of alkene to form carbocation by electrophilic attack of H3O+

Q.How are the following conversions carried out?

(i) Propene to propan-2-ol
(ii) Ethyl magnesium chloride to propan-1-ol.
(iii) Benzyl chloride to benzyl alcohol,
(iv) Methyl magnesium bromide to 2-methylpropan-2-ol.
(v) Phenol to 2, 4, 6-trinitrophenol
(vi) Phenol to 2, 4, 6-tribromophenol
(vii)Ethene to propane-1ol
(viii) Ehtanal to Propan-2-ol
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Ans. (i) Propene to propane -2-ol

(ii) Ethyl magnesium chloride to propan-1-ol

(iii) Benzyl chloride to benzyl alcohol

(v) Phenol to 2,4,6- trimnitrophenol

(vi) Phenol to 2, 4, 6-tribromophenol: Phenol reacts with bromine in presence of polar solvent H2O to form 2, 4, 6-
tribromophenol (white ppt.)

(vii) Ethene to propane -1-ol

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Q.Write the structures of the products when Butan-2-ol reacts with the following:
(a) CrO3
(b) SOCl2

Ans.

Q. How would you obtain the following :

(i) 2-methylpentan-2-ol from 2-methyl-1-pentene
(ii) Acetophenone from phenol.

Ans. (i) 2-Methylpentan-2-ol from 2-methyl-1-pentene

Q.a) Give mechanism of preparation of ethoxy ethane from ethanol.

(b) How is toluene obtained from phenol?
Ans.(a) Mechanism of formation of ethoxy ethane
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Step 1 : Protonation of ethanol

Q.What is meant by hydroboration-oxidation reaction? Illustrate it with an example.

Ans: The addition of diborane to alkenes to form trialkyl boranes followed by their oxidation with alkaline
hydrogen peroxide to form alcohols is called hydroboration-oxidation. For example,

Q.Give the equations of the reaction for the preparation of phenol from cumene.
Ans: This process has a great industrial importance because it gives the preparation of two very useful compounds
i.e. phenol and acetone. The raw materials are benzene and propene and it initially proceeds by Friedel Crafts
alkylation of benzene.
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Q. Give a seperate chemical test to distinguish between the following pairs of compounds:
(i) Ethanol and Phenol (ii) 2-Pentanol and 3-Pentanol

Ans. (a) (i) Ethanol on reacting with I2 in NaOH gives yellow ppt of iodoform whereas phenol does not respond to
this test.
(ii) 2-Pentanol on reacting with I2 in NaOH gives yellow ppt of iodoform whereas 3-pentanol does not respond to
this test.

Q. Explain the fact that in alkyl aryl ethers, alkoxy group :

(i) activates the benzene ring towards electrophilic substitution.
(ii) directs the incoming substituents towards ortho and para positions in the ring.
Ans:
(i) The alkoxy group (RO -) with lone electron pairs on the oxygen atom activates the ortho and para positions in
the ring by + M (or + R) effect as shown below :
As the ortho and para positions in the ring become points of high electron density, the electrophiles prefer to
attack these positions.

(ii) The alkoxy group directs the incoming group which is an electrophile towards the ortho and para positions in
the ring. As a result, a mixture of isomeric products is formed.

Q. Write the mechanism of the reaction of HI with methoxymethane.

Ans: When equimolar amounts of HI and methoxy methane are reacted, a mixture of methyl alcohol and methyl
iodide is formed by the following mechanism:
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Q. Differentiate between alcohol and phenol

Difference Between Alcohol and Phenol

Alcohol Phenol

The alcohols are a class of organic compounds that Phenols, on the other hand, are organic compounds
hold at least one hydroxyl functional group that is consisting of a hydroxyl group which is attached to an
attached to a carbon atom. aromatic system of hydrocarbons (arene).

Alcohols usually feature the hydroxyl group attached to Phenols usually contain aromatic hydrocarbons.
aliphatic hydrocarbons.

In comparison to phenol, alcohols are known to be less Phenols are relatively more acidic in nature and should,
acidic. therefore, be diluted before usage.

In terms of usage, alcohol is the main ingredient in Phenols are mainly used in medicinal products as
alcoholic beverages. They are also used in ink, pharma, antiseptic agents.
ink and many other industries.

Alcohols are mostly colourless, and they usually exist in Phenols are colourless solids that usually exist as crystals
the liquid state. at STP.

Alcohols show no impact or reaction during tests as Phenol can change litmus paper red as they are acidic in
they are mostly neutral. nature.

Q.To distinguish between phenol and benzoic acid?

Ans. consider the following reactions:

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C6H5OH+FeCl3→[Fe(OC6H5)]3−+3H++3Cl−

C6H5COOH+FeCl3→ No reaction

Here it can be seen that the phenol reacts with the ferric chloride and Iron phenol complex which is violet in colour whereas

the benzoic acid does not give this test.

Q. a. Give reasons for the following: (i)The reaction of ethanol with acetyl chloride is carried out in the
presence of pyridine . (ii) Cresols are less acidic than phenol.
b. Williamson’s process is used for the preparation of ethers from alkyl halide. Identify the alkyl bromide
and sodium alkoxide used for the preparation of 2- Ethoxy-3-methylpentane

Ans a. (i) The reaction of ethanol with acetyl chloride is carried out in the presence of pyridine . Pyridine is a strong
organic base .The function of pyridine is to remove HCl formed in the reaction.

(ii) The electron releasing groups, such as alkyl groups, in general, do not favour the formation of phenoxide ion
resulting in decrease in acid strength. Cresols, for example, are less acidic than phenol.

b. C2H5Br and CH3CH2CH(CH3)CH2CH2ONa yields 2- ethoxy-3-methylpentane

Q a. Out of formic acid and acetic acid, which one will give the HVZ reaction? Give a suitable reason in
support of your answer and write the chemical reaction involved.

b. Alcohols are acidic but they are weaker acids than water.

Arrange various isomers of butanol in the increasing order of their acidic nature. Give a reason for the
same.

Ans Acetic acid will give HVZ reaction. Carboxylic acids having an α-hydrogen are halogenated at the α-position on
treatment with chlorine or bromine in the presence of a small amount of red phosphorus to give α-halo carboxylic
acids. CH3COOH Br2/red P CH2BrCOOH

a. Isomers of butanol are: Butan-1-ol , butan-2-ol , 2-methylpropanol , 2-methylpropan-2-ol . Acidic strength

in isomeric alcohols varies as follows
The acidic character of alcohols is due to the polar nature of O–H bond. An electron-releasing group (–CH3 ,
–C2H5 ) increases electron density on oxygen tending to decrease the polarity of O-H bond 2-
methylpropan-2-ol< 2-methylpropanol < butan-2-ol