PU–2–IMP Alcohols, Phenols and Ethers

Blue Print (As per PU Board)

1 mark 2 marks 3 marks 5 marks Total Marks

Topic
questions questions questions questions
Alcohols, Phenols and
– 1 – 1 7
Ethers

One mark questions

1. Give an example for dihydric alcohol
Answer: CH OH or CH2 OH
2

CH 2 OH CH 2

CH 2 OH
2. Give an example for a trihydric alcohol
Answer: CH OH2

CH OH

CH 2 OH

3. What are allylic alcohols?

Answer: Alcohols in which an hydroxyl group is attached to SP3 carbon atom which in turn is bonded
to a SP 2 carbon atom (double bond)

4. Give the general equation of William son’s ether synthesis

Answer: R  X  R ' O  Na  R  O  R ' NaX

Two marks questions

5. Predict the products of the following

OC2H5
(a) + HBr
(1 mark)
(b)  CH3 3 C  OC2 H5  HI 
 (1 mark)
OH
Answer:
(a) + CH 3 CH 2 Br
Bromoethane
Phenol

CH3
(1+1 mark)
(b) CH 3 C CH 3 + C2H5OH
I
t - butyl iodide ethanol

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PU–2–IMP Alcohols, Phenols and Ethers

6. Complete the reactions

Cu
(i) R  CH 2  OH 
573 K

H
(ii) CH3  CH  CH 2  H 2O 

Answer: (i) R  CHO  H 2 or R  CHO (1 mark)
(ii) CH 3 CH CH3
OH (1 mark)
7. Explain Williamson’s ether synthesis with an example.
Answer: Bromoethane reacts with alcoholic solution of sodium ethoxide to form diethyl ether is called
Williamson’s ether synthesis. (1 mark)
Alcohol
C2 H5 Br  C2 H5ONa 
 C2 H5  O  C2 H5  NaBr (1 mark)

8. What is Lucas reagent? Between primary and tertiary alcohols, which one of these will react faster
with Lucas reagent?
Answer: Conc. HCl  antiydrousZnCl2 (1 mark)
Tertiary alcohol (1 mark)

Five marks questions

9. (a) Explain with equations:

(i) Kolbe’s reaction
(ii) Williamson’s ether synthesis
(b) A carbonyl compound    with the formula C2 H 4O reacts with CH3 MgX followed by hydrolysis
to form an alcohol Q . Name the alcohol Q . (4+1 Marks)
Answer: (a) (i) Kolbe’s reaction: Sodium phenate undergoes electrophilic substitution reaction with
CO2 to finally form salicylic acid as main product. (1 mark)
ONa OH
COOH
(i) CO 2
+
(ii) H

or (1 mark)
ONa OH
COOH
(i) CO 2
+
(ii) H

sodium phenate 2 - hydroxy benzoic acid

(salicylic acid) (2 marks)
(ii) Williamson’s ether synthesis: Alkyl halide reacts with alcoholic sodium alkoxide to form ether as
main product. (1 mark)
R  X  Na O  R ' 
 R  O  R  NaX (1 mark)
Alkylhalide sodium alkoxide ether

(b) Q is propan  2  ol (1 mark)

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PU–2–IMP Alcohols, Phenols and Ethers

10. (a) With equation, give an example for

(i) Reimer Tiemann reaction
(ii) Dehydration of a primary alcohol
(b) Complete the following equation
OH


+Zn

(4+1 Marks)
Answer: (a) (i) Reimer –Tiemann reaction
Phenol reacts with chloroform in presence of NaOH to form a product which on acidification gives
salicylaldehyde.
OH
ONa ONa

CHCl 2 CH(OH) 2
CHCl 3 + NaOH 2 NaOH

Intermediate

ONa OH
CHO CHO
+
H
-H 2O

2 - Hydroxy benzaldehyde
(salicylaldehyde) (1 mark)
(ii) Dehydration of a primary alcohol
Ethyl alcohol when heated with concentrated sulphuric acid dehydrates to form acetaldehyde (ethanal)
(1 mark)
Conc.H SO
CH3  CH 2  OH 
2 4  CH CHO
3 (1 mark)

OH

(b) 
+ Zn + ZnO

Benzene (1 mark)
11. (a) Name the major product formed when the vapours of following alcohols are passed over hot
copper at 573 K

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PU–2–IMP Alcohols, Phenols and Ethers

(i) CH 3CH(OH) CH 3

CH 2OH
(ii)

CH3
(iii) CH 3 C OH
CH3
(b) Explain friedel –crafts reaction by taking anisole as an example
Answer: (a) (i) Acetone or propan 2  one (1 mark)
(ii) Benzaldehyde (1 mark)
(iii) 2  methyl prop 1  ene (1 mark)
(b) Anisole reacts with acetyl chloride in presence of anhydrous aluminium chloride catalyst to give
2  Methoxy acetophenone and 4  Methoxy aceto-phenone (1 mark)
OCH3 OCH 3 OCH 3
COCH 3
anhydrous
+2CH3COCl + 2 HCl
AlCl3


COCH 3
(1 mark)
12. (a) Explain the mechanism of dehydration of ethanol to ethene
(b) On treating phenol with chloroform in presence of aqueous sodium hydroxide at 340 K followed
by acid hydrolysis gives the product
(i) Write the name of the product
(ii) Give the name of the reaction (3+2 marks)
Answer: (a) Mechanism
Step-1: Protonation of protonated alcohol
H H H H
fast
H C C O H H H C C O H
H H H H H

ethanol protonated alcohol (1 mark)

Step-2: Formation of carbocation by loss of water from the protonated alcohol.
H H H H
slow step
H C C O H H C C H2O
r.d.s
H H H H H (1 mark)
Step-3: Formation of alkene (ethene) from the carbocation by elimination of proton.
H H H H
H C C C C +H+

H H
H H
Ethene
(1 mark)
(b) (i) Salicylaldehyde (1 mark)
(ii) Reimer- Tiemann reaction (1 mark)
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