GRADE XII GRADE XII

ALCOHOLS, PHENOLS AND ETHERS

WORKSHEET
Date of Issue : Date of Submission: 11.
Name of the student: Section :
General instructions :
• Answer all the questions 12.
IUPAC NAMES
Write the IUPAC name of the following compound:
13.
1.

2.

3. 14.

4. 15.

16.
5.
17.
6.

7.
18.
19. Write the structure of the molecule of a compound whose IUPAC
8. name is 1-phenylpropan-2-ol
20. Draw the structural formula of 2-methylpropan-2-ol molecule.
21. Draw the structure of 2, 6-Dimethylphenol
22. Draw the structure of hex-1-en-3-ol compound.
9. 23. Write the structures of the products when Butan-2-ol reacts with the
following:
(a) CrO3
10. (b) SOCl2
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24. Draw the structure and name the product formed if the following
alcohols are oxidized. Assume that an excess of oxidizing agent is
used. 4. Write the mechanism (using curved arrow notation) of the following
(i) CH3CH2CH2CH2OH reaction:
(ii) 2-butenol
(iii) 2-methyl-1-propanol
NAMING REACTION
Give a chemical equation for each of the following reactions:
(i) Williamson’s synthesis
(ii) Reimer-Tiemann reaction 5. Write the mechanism (using curved arrow notation) of the following
(iii) Kolbe's reaction reaction:
(iv) Friedel-Crafts reaction.
(v)Friedel-Crafts’ acetylation of anisole.

CHEMICAL TEST TO DISTINGUISH

✓ Phenol and benzoic acid
✓ Phenol and ethanol
✓ Propan-2-ol and 2-methylpropan-2-ol 6. Arrange the following compounds in the increasing order of their
✓ Ethanol and diethyl ether acid strength:
✓ Propanol and tertiary butyl alcohol/ 2-methylpropan-2-ol (i) p-cresol, p-nitrophenol, phenol
MECHANISM AND ITS BASED QUESTION (ii) Benzoic acid, phenol, cresol
1. Alcohols react both as nucleophiles as well as electrophiles. Write (iii)p-nitrophenol, ethanol, phenol
one reaction of each type and describe its mechanism. (iv) Ethanol, Phenol, water.
2. Explain the mechanism of the following reactions: 7. Give reason
(i) Addition of Grignard’s reagent to the carbonyl group of a compound (i) Ortho-nitrophenol is more acidic than ortho-methoxyphenol
forming an adduct followed by hydrolysis. Because NO2 is an electron withdrawing group
(ii) Acid catalysed dehydration of an alcohol forming an (ii) o-and p-nitrophenols are more acidic than phenol.
alkene/Dehydration of ethanol, giving ethene. (iii)p-nitrophenol is more acidic than p-methylphenol.
(iii) Acid catalysed hydration of an alkene forming an alcohol/Hydration Due to –I / –R effect of –NO2 group & +I / +R effect of –CH3
group or 4-nitrophenoxide ion is more stable than 4-
of ethene to yield ethanol. methylphenoxide ion
3. Write the mechanism of the following reactions: (iv) p-nitrophenol is more acidic than o-nitrophenol.
Due to intramolecular H-bonding in o-nitrophenol /p-nitrophenoxide
is more stabilized than o-nitrophenoxide due to more delocalization
(or) of the negative charge.
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(v) Phenol is more acidic than ethanol/ methanol. (vii) (CH3)3C – O – CH3 on reaction with HI gives (CH3)3C –I and
Phenoxide ion is stabilized by resonance as compared to CH3O – / CH3 –OH as the main products and not (CH3)3C – OH and CH3–I.
In phenol, oxygen acquires + ve charge due to resonance and (CH3)3C+ is 3º carbo-cation which is more stable than CH3+ for
SN1 reaction. (Or) Because it follows SN1 path way which results
releases H+ ion easily whereas there is no resonance in methanol.
in the formation of stable (CH3)3C+.
(Or) (viii) (CH3)3C – Br on reaction with NaOCH3 gives an alkene instead
Because phenoxide ion is more stable than CH3CH2O – ion / due of an ether.
to resonance in phenol, oxygen acquires positive charge and (CH3)3C–Br being a 3º halide prefers to undergo β – elimination
releases H+ ion easily whereas there is no resonance in CH3CH2 on reacting with strong base like NaOCH3. Or CH3ONa is not
OH only nucleophile but also stronger base, thereby leads to
(vi) o-nitrophenol is more steam volatile than p-nitrophenol. elimination reaction of the alkyl halide.
(ix) Protonation of phenol is difficult whereas ethanol easily
o-Nitrophenol is steam volatile due to intramolecular hydrogen
undergoes protonation.
bonding while p-nitrophenol is less volatile due to intermolecular In phenols lone pair of electron on oxygen are delocalized over
hydrogen bonding. benzene ring due to resonance but in alcohol lone pair of
electron on oxygen are localized & hence available for
GIVE REASON protonation / + R- effect in phenol but not in ethanol
Explain the following observations: (x) Anisole on reaction with HI gives phenol and CH3I as main
(i) Boiling point of ethanol is higher in comparison to products and not iodobenzene and CH3 OH.
methoxymethane / dimethyl ether / diethyl ether. Weaker (O-CH3) bond and stronger(O-C6H5) bond ,due to
Because of hydrogen bonding in ethanol resonance / carbon in benzene is sp2 hybridized due to which
(ii) Alcohols are more soluble in water than the hydrocarbons of partial double bond character.
comparable molecular masses. (xi) t-butyl chloride on heating with sodium methoxide gives 2-
(iii)Bond length of C – O bond in phenol is shorter than that in methylpropene instead of t-butylmethylether.
methanol. Due to the formation of stable intermediate tertiary carbocation
(iv) (CH3)3C – Br on reaction with sodium methoxide (Na+–OCH3) / CH3O- being a strong base favours elimination reaction.
gives alkene as the main product and not an ether. (xii) Phenol undergoes electrophilic substitution more easily than
(CH3)3C–Br being a 3º halide prefers to undergo β – elimination benzene.
on reacting with strong base like NaOCH3. Due to involvement of lone pair of oxygen in delocalisation
(v) The C – O – H bond angle in alcohols is slightly less than the makes the benzene ring electron rich.
tetrahedral angle (109°28’).
Due to lone pair- lone pair repulsion on oxygen. OTHER QUESTIONS:
(vi) Bond angle C – O – C in ethers is slightly higher than the 1. Arrange the following compounds in the increasing order of their
tetrahedral angle (109º28º). property indicated:
The mutual repulsion between bulky alkyl group is stronger than (i) CH3CH2OH, CH3CHO, CH3 – O – CH3 (boiling point)
the lp – lp electronic repulsion
(ii) Propanol, Propane, Propanal (boiling point)
Class XII/Chemistry /Alcohols, Phenols & EthersWorksheet /2020
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2. Name the reagents which are used in the following conversions:
(i) A primary alcohol to an aldehyde
(ii) Butan-2-one to butan-2-ol
(iii) Phenol to 2, 4, 6-tribromophenol
3. Write the formula of reagents used in the following reactions: 5.
(i) Bromination of phenol to 2,4,6-trinitrophenol
6.
(ii) Hydroboration of propene and then oxidation to propanol.
4. Of the two alcohols; (a) CH2=CH—CH2OH and (b) CH2=CH—
CH2—CH2OH, which one will react more easily with conc. HCl in
the presence of ZnCl2? 7.
5. How will you synthesise the following alcohol from appropriate
alkene : 8.

9.

10.

11.
COMPLETE THE REACTION:
State the products of the following reactions: 12.

1.
13.
2.

3.
14.
4.
15.

Class XII/Chemistry /Alcohols, Phenols & EthersWorksheet /2020

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16.

17. 5. Benzyl chloride to benzyl alcohol

6. ethanol to ethane
7. Ethyl chloride to methoxy ethane
18.

19. 8. Ethyl magnesium chloride to propan-1-ol

9. 2-Methylpropan-2-ol from methylmagnesium bromide / Propanone
to 2-methylpropan-2-ol
20.
10. 2-Methylpropene from 2-methylpropanol
21. 11. Phenol to 2-hydroxyacetophenone
12. Phenol to anisole
22. 13. Phenol to benzoquinone

CONVERSION

How would you carry out the following conversions?

1. Acetone to 2-methylpropan-2-ol
14. Picric acid (2, 4, 6-trinitrophenol) from phenol,
15. Prop-1-ene to Propan-1-ol

16. Propan-2-ol from propane

2. Aniline to phenol
17. Propan-2-ol to 2-methylpropan-2-ol
18. Propene to propan-2-ol
3. Anisole to 2-methoxytoluene
OR
What happens when
1. (CH3)3C – OH is treated with Cu at 573K
4. Benzoquinone from phenol 2. (CH3)3C – OH is treated with HI
3. Anisole is treated with CH3Cl / anhydrous AlCl3
4. Anisole is treated with CH3COCl / anhydrous AlCl3
5. Anisole reacts with HI ?
6. CH2=CH – CH2 – OH is oxidized by PCC?
Class XII/Chemistry /Alcohols, Phenols & EthersWorksheet /2020
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7. Ethanol is treated with Cu at 573 K,

8. Ethanol reacts with CH3COCl/pyridine ?

9. Ethyl chloride is treated with NaOCH3 ?
10. Phenol is oxidized with Na2Cr2O7 / H+?
11. Phenol is treated with Br2/CS2?
12. Phenol reacts with Bromine water ?
13. Phenol with chloroform in the presence of aq. NaOH
14. Phenol is treated with CH3COCl / anhydrous AlCl3?

15. Phenol is treated with Zn dust?

16. Phenol reacts Con HNO3
17. Salicylic acid reacts with (CH3CO)2O / H+.
18. Sodium phenoxide is treated with CH3Cl?
Write the chemical equations involved in the above reactions.
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Class XII/Chemistry /Alcohols, Phenols & EthersWorksheet /2020