Chapter - 11

ALCOHOLS, PHENOLS AND ETHERS

1. Write IUPAC names of the following compounds :

(ix) C6H5OC3H7
(x) CH3CH2OCH2CH2CH2Cl
2. Write the structures of the compounds whose names are given below :
(i) 3, 5-dimethoxyhexane-1, 3, 5-triol
(ii) cyclohexylmethanol
(iii) 2-ethoxy-3-methylpentane
(iv) 3-chloromethylpentan-2-ol
(v) p-nitroanisole
3. Describe the following reactions with example :
(i) Hydroboration oxidation of alkenes
(ii) Acid catalysed dehydration of alcohols at 443K.
(iii) Williamson synthesis
(iv) Reimer-Tiemann reaction.
(v) Kolbe’s reaction
(vi) Friedel-Crafts acylation of Anisole.
4. Complete the following reactions :

1 2
 5. What happens when :
(i) aluminium reacts with tert-butyl alcohol
(ii) phenol is oxidised with chromic acid
(iii) cumene is oxidised in the presence of air and the product formed
is treated with dilute acid.
(iv) phenol is treated with conc. HNO3.
(v) phenol is treated with chloroform in presence of dilute NaOH.
6. How will you convert
(i) propene to propan-l-ol.
(ii) anisole to phenol
(iii) butan-2-one to butan-2-ol
(iv) ethanal to ethanol
(v) phenol to ethoxybenzene
(vi) 1-phenylethene to 1-phenylethanol
(vii) formaldehyde to cyclohexylmethanol
(viii) butyl bromide to pentan-1-ol.
(ix) toluene to benzyl alcohol
(x) 1-propoxypropane to propyl iodide
(xi) ethyl bromide to 1-ethoxyethane
(xii) methyl bromide to 2-methoxy-2-methylpropane
(xiii) ethyl bromide to ethoxybenzene
(xiv) ethanol to benzyl ethyl ether.

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 +
7. Identify the missing reactant or product A to D in the following equations: (ii) CH3 – CH2 – OH
H
 → CH2 = CH2
443 K
(acid catalysed dehydration of alcohols)
+
H
(iii) 2CH3CH2OH 
413 K
→ CH3CH2OCH2CH3
(acid catalysed nucleophilic substitution reaction)

(iv) CH3OCH3 + HI 
→ CH3OH + CH3I

(v) (CH3)3C – O – CH3 + HI 

→ CH3OH + (CH3)3 CI

11. Give reason for the following :

(i) The C–O–C bond angle in dimethyl ether is (111.7°)
(ii) Alcohols have higher boiling points than ethers of comparable
molecular masses.
8. Identify X, Y and Z in the following sequence of reactions : (iii) Phenols are more acidic than alcohols.
(iv) Nitrophenol is more acidic than o-methoxyphenol.
(v) Phenol is more reactive towards electrophilic substitution reaction
than benzene.
(vii) The following is not an appropriate method for the preparation of
t-butyl ethyl ether :

(a) What would be the major product of this reaction?

(b) Write suitable reaction for the preparation of t–butyl ethyl ether.

10. Write the mechanism for following reactions : (viii) The following is not an appropriate method for the preparation of
1-methoxy-4-nitrobenzene;

(acid catalysed hydration of alkenes)

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 (x) Write the suitable reaction for the preparation of
1–methoxy–4–nitrobenzene
(ix) o-nitrophenol is steam volatile but p-nitrophenol is not.
(x) phenol is less polar than ethanol.
(xi) The phenyl methyl ether reacts with HI fo form phenol and
iodomethane and not iodobenzene and methanol.
*15. What is the function of ZnCl2 (anhyd) in Lucas test for distinction between
1°, 2° and 3° alcohols.
16. An alcohol A (C4H10O) on oxidation with acidified potassium dichromate
gives carboxylic acid B (C4H8O2). Compound A when dehydrated with
conc. H2SO4 at 443 K gives compound C. Treatment of C with aqueous
(xii) methanol is less acidic than water.
H2SO4 gives compound D (C4H10O) which is an isomer of A. Compound
(xiii) alcohols can act as weak base as well as weak acids. D is resistant to oxidation but compound A can be easily oxidised. Identify
(xiv) phenols do not give protonation reaction readily. A, B, C and D and write their structures.
[Ans. : [A] : (CH3)2CHCH2OH [B] : CH3CH(CH3)COOH
(xvi) absolute ethanol can not be obtained by factional distillation of ethanol
and water mixture. [C] : (CH3)2C = CH2 [D] : (CH3)3C – OH
12. Arrange the following in the increasing order of property shown : *17. An organic compound A having molecular formula C 6H 6O gives a
(i) methanol, ethanol, diethylether, ethyleneglycol. (Boiling points) characteristic colour with aqueous FeCl3. When A is treated with NaOH
and CO2 at 400 K under pressure, compound B is obtained. Compound
(ii) phenol, o-nitrophenol, m-nitrophenol, p-nitrophenol. (Acid strength) B on acidification gives compound C which reacts with acetyl chloride to
(iii) dimethylether, ethanol, phenol. (Solubility in water) form D which is a popular pain killer. Deduce the structure of A, B, C and
(iv) n-butanol, 2-methylpropan-1-ol, 2-methylpropan-2-ol. (Acid strength) D. What is the common name of Drug D?

13. Give a chemical test to distinguish between the following pair of compounds.
(i) n-propyl alcohol and isopropylalcohol
(ii) methanol and ethanol
(iii) cyclohexanol and phenol.
(iv) propan-2-ol and 2-methylpropan-2-ol.
(v) phenol and anisole
(vi) ethanol and diethyl ether
*14. Which of the following compounds gives fastest reaction with HBr and
why? 19. An ether A (C5H12O) when heated with excess of hot concentrated HI
(i) (CH3)3COH produced two alkyl halides which on hydrolysis from compounds B and C.
Oxidation of B gives an acid D whereas oxidation of C gave a ketone E.
(ii) CH3CH2CH2OH
Deduce the structures of A, B, C, D and E.

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 [Ans. : (A)

(B) CH3CH2OH
(C) CH3CHOHCH3
(D) CH3COOH
(E) CH3COCH3
20. Phenol, C6H5OH when it first reacts with concentrated sulphuric acid, forms
Y.Y is reacted with concentrated nitric acid to form Z. Identify Y and Z and
explain why phenol is not converted commercially to Z by reacting it with
conc. HNO3.
[Ans. :

Phenol is not reacted directly with conc. HNO3 because the yield of picric
acid is very poor]
21. Synthesise the following alcohols from suitable alkenes.

22. How are the following ethers prepared by williumson synthesis?

(a) Ethoxybenzene (b) 2–methoxy–2–methylpropane