Chemistry : Alcohols, Ethers and Phenols

ASSIGNMENTS

SECTION - I
SUBJECTIVE QUESTIONS
LEVEL - I
1. Explain why ortho-nitrophenol is more acidic than ortho-methoxyphenol?
2. Why (CH3)3COH is less acidic than (CH3)3SiOH although carbon is more electronegative than Si?
3. What is the order of dehydration of following compounds?
(i) pO2NC6H4CH(OH)CH3 (ii) pH2NC6H4CHOH CH3
(iii) C6H5 CHOH CH3

CH3 CC CH3I  H2 / Pd / BaSO 4

4. CH3CH—CH2     A    B      C What are A,B and C?
O

OCH3 O

5. H
   CH 3OH
H2 O

6. Alcohols are weaker acids than phenols but are stronger nucleophiles - explain.
7. Phenol is not soluble in aquous NaHCO3 but acetic acid is soluble - Explain.
8. Write the mechanism and comment on the migratory aptitudes in the reaction of aliphatic hydroperoxides
with aqueous acids to give only aldehydes and ketones as the major products.
9. Convert
(a) acetylene into n-butyl alcohol and (b) propane into allyl alcohol
10. Identify all unknown structures
OH

CrO 3 (i) CH 3 MgI H 2SO 4 (i) BH 3 , THF


H SO
A 
(ii) H O 
B 
C 
(ii) H O , OH
D
2 4 3 2 2

LEVEL - II
1. Write the equation for the reaction of hydrogen iodide with
(i) 1–propoxypropane
(ii) methoxybenzene
(iii) benzyl ethyl ether
 Chemistry : Alcohols, Ethers and Phenols

2. Explain pKa values of the following phenol derivative.

Group o m p
NO2 7.23 8.35 7.14
Me 10.28 10.08 10.19
Cl 8.48 9.02 9.38
OMe 9.98 9.65 10.21

LAH PBr3 Alcoholic KOH

 
dry ether
 A   B  C
3.
O

What are A to C?
4. Starting from CH3—CHO as the carbonyl compound suggest the grignard reagent which you should
use to prepare the following compounds.
(i) 2, methyl, 2, propanol
(ii) Acetophenone (Phenyle methyle ketone)

OH

(iii) CH2 C CH3

CH3

5. Predict A, B and C in the following sequence of reaction and also explain their formula.

PBr3
A  Mg
 B 
Dry ether
 Grignard 's Re agent C 
H 3O 
 3, 4 dim ethyl  3  hexanol

6. An organic compound A on treatment with acetic in the presence of sulphuric acid produces an ester
B. A on mild oxidation gives C which with 50% KOH followed by acidification with dilute HCl generates
A and D. D with PCl5 followed by reaction NH3 gives E. E on dehydration produces phenyl cyanide.
Identify A, B,C,D and E

OH

7. , give details of conversion.

8. Compound (A) reacts with sodium to liberate H2, forming a compound (B). When (A) is treated with
HCl + ZnCl2, an immediate reaction takes place liberating (C). When (A) is heated with H2SO4, (D) is
formed. Ozonolysis of (D) gives a 3 carbon aldehyde and 3 carbon ketone. What are (A), (B), (C) and
(D).
Chemistry : Alcohols, Ethers and Phenols

9. Devise a synthesis of the following compound, starting from toluene and using any necessary reagents.

COOH

Ph

CH3
H3C H3C

CH3
CH3

10. 
HCl ?
OH

LEVEL - III
1. Give equations of the following reactions :
(i) reaction of propene with mercuric acetate followed by hydrolysis
(ii) oxidation of propan–1–ol with alkaline KMnO4 solution
(iii) reduction of bromine in CS2 with phenol
(iv) action of dilute nitric acid with phenol
(v) treating phenol with chloroform in presence of aqueous NaOH at 343 K
2. An open chain compound (A) C5H8O is optically active. When (A) is hydrogenated in presence of Pd
as catalyst, it absorbs two moles of H2 per mole of (A) to produce compound (B) C5H12O which is
optically inactive. However when (A) is warmed with dilute H2SO4 in presence of HgSO4 it gives
compound C(C5H10O2) which is still optically active. C responds to iodoform test. What are the structures
of A to C?
3. An organic compound (A) C10H12O gives red colour when treated with cerric ammonium nitrate and
also decolourises Br2 in CCl4 to give B(C10H12OBr2). A can show both geometrical and optical isomerism.
A on treatment with I2 and NaOH gives iodoform and an acid (C) after acidification. Give the structures
of A to C and also the stereoisomers of A.
4. Write the products in the following reactions.
CH CH2
(i) Ph CH
Ph Mg Br
OH 


(ii) OH CH 3MgBr
 
H3C

(iii) O NaBH 4
O  

Ni / H 2
(iv) Ph CH CH C CH CH2  
 Chemistry : Alcohols, Ethers and Phenols

5. Explain the formation of products (X) and (Y) from respective reagents (A) and (B).

O OMgBr

Ph Mg Br
Ph CH3   Ph CH3 X
Ph

O
OMgBr
Ph Mg Br
Ph CMe3   Ph CH CH C Y

Ph CMe3

CH3

6. Show how would you synthesise C OH with starting reagents containing not more than

CH2
H3C

5C atoms.

7. p-nitrophenol reacts with ethyl bromide and aq NaOH to give a compound A (C8H9O3N). A on treatment
with Sn and HCl gives B (C8H11ON). B on treatment with NaNO2, HCl and then with phenol gives C
(C14 H14 O2N2). C on reation with ethyl sulfate and aqueous NaOH gives D (C 16 H18 O2 N2 ). D on
treatment with SnCl2 gives E (C8H11ON). E reacts with acetyl chloride to give phenacetin (C10H13O2N).
Identify structure from A to E.
8. An alkene (A) yields a tertiary alcohol (C) containing an asymmetric carbon on oxymercuration -
demercuration reaction. Another isomeric alkene (B) gives the same alcohol (C) as one of the products
under the same reaction condition. On vigorous oxidation with KMnO4, (A) gives a carbonyl compound
(D) containing five carbon atoms and an acid (E) containing four carbon atoms. The carbonyl compound
(D) on reduction with LiAlH4 gives an optically active alcohol (F), containing two identical alkyl groups
on the same carbon atom.On the other hand alkene (B) gives on vigorous KMnO4 oxidation two
carbonyl compounds (G) and (H). (H) contains six carbon atoms and no two identical groups are
attached to the same carbon atom. Give the structures of (A) to (H) showing the reactions clearly.
9. Predict the product(s) of each reaction below. Be sure to specify the stereochemistry where appropriate.
(Ph, phenyl; *, isotope label)
(a) Ph—O—CH2—Ph 
excess HI

(b) (H3C)2CH—O—C(CH3)3 
1 equiv. HBr

O

1. PhO
(c) 
2. H 
Ph
Chemistry : Alcohols, Ethers and Phenols

(d) H H2 O
 
H H CH2CH3 H  (cat.)

(e) H 
H H CH2CH3
1. OH
 
2. H 

H
(f) O 1. PhLi
 
2. H 

CH3

10. 0.037g of an alcohol, ROH, was added to CH3MgI and the gas evolved measured 11.2 cm3 at STP.
What is the molecular weight of ROH? On dehydration, ROH gives alkene which in ozonolysis gives
acetone as one of the products. ROH on oxidation easily gives an acid containing the same number of
carbon atoms. Give structure of ROH and the acid containing the same number of carbon atoms. Give
structure of ROH.
 Chemistry : Alcohols, Ethers and Phenols

SECTION - II
SINGLE CHOICE QUESTIONS
CH3 CH3
HBr
1. H3C   A (predominant)

CH3 OH
A is:
CH3 Br Br CH3

(a) H3C (b) H3C

CH3 CH3 CH3 CH3

(c) Both (d) None is correct

2. The relative order of acidity of alcohols in comparison to H2O and HC  CH is
(a) H2O  ROH  HC  CH (b) H2O  HC  CH  ROH
(c) ROH  H2O  HC  CH (d) ROH  HC CH  H­2O
3. Which of the following compounds gives most stable carbonium ion on dehydration?

CH3

(a) H3C C OH (b) H3C CH CH2 OH

CH3 CH3

(c) H3C CH CH2 CH2 (d) CH3 CH 2 CH 2CH 2 OH

OH
4. The correct decreasing order of acidic strength is
(a) C6H5OH  C6H5CH2OH  C6H5COOH  C6H5SO3H
(b) C6H5CH2OH  C6H5OH  C6H5SO3H  C6H5COOH
(c) C6H5COOH  C6H5CH2OH  C6H5OH  C6H5SO3H
(d) C6H5SO3H C6H5COOH  C6H5OH  C6H5CH2OH
5. In which of the following case configuration about chiral C* is retained:
Me Me

Na CH Br CH ONa
(a) Ph OH  
3
 (b) Ph OH 
TsCl
 
3


Et Et
Me
PCl CH Br
(c) Ph OH 
5
 
3
 (d) None of these.

Et
Chemistry : Alcohols, Ethers and Phenols


6. H
  what would be (X)
OH

(a) (b)
O O
Me

(c) CH2 CH3 (d)

O
O
CH3

7. Hydration of 3-phenyl-1-butene in dilute H2SO4 gives:

C6 H5
C 6 H5

(a) (b) H3C CH3

HO CH3
OH

OH

CH3
(c) (d) None of the above
H3C C6H5


H
8. The reaction CH2 
H2O
; gives

CH3

(a) OH (b)
OH

OH

(c) CH3 (d) None of the above

9. The alcohol, C4H9OH when treated with a mixture of anhydrous. ZnCl­2 and conc.HCl gave an
immediate oily layer. It will be
CH3
H3C
(a) H3C OH (b)
OH
CH3 H3C
H3C

(c) OH
(d)
H3C H3C OH
 Chemistry : Alcohols, Ethers and Phenols

10. Which of the following give positive iodoform test?

CH3 OH CH3

H3C H3C
(a) (b)
CH3 CH3 CH3 OH

CH3 CH3
O
H3C CH3
(c) (d)
OH CH3 H3C CH2 CH3

OH Al2 O3
  A i) HI
B
350 C ii) AgOH
11. Write the final product of the following reaction: H3C
Product (B) is:
OH

H3C O CH3
(a) (b) H C
3
CH3

H3C O H3C
(c) (d)
CH3 CH2
12. Which one of the following will most readily be dehydrated in acidic solution?
OH
O OH

(a) (b) H3C CH3

H3C CH3
O
OH O

CH3
(c) H3C CH3 (d) H3C
OH OH
13. Consider the following pairs of alcohols (1,2,3,4):

H3C OH and H3C

(a) OH

H3 C

CH3
HO CH3
H3C and
(b)
OH CH3 H3C CH3
Chemistry : Alcohols, Ethers and Phenols

CH3 OH
CH3 CH3
(c) and
OH CH3
H3C CH3

(d) and OH

OH
14. Which of the following decreasing order of rate of dehydration with H2SO4 is correct for the alcohols.
OH
OH OH

CH3 C CH2 C (CH3)2

(H3 C)2 CH2 CH3 (H3 C)2 CH
CH3 (A) (B) (C)

CH2 CH
H3C CH (CH3 )2 OH
H3C
OH
(D) (E)

(a) C > B > D >A> E (b) E > A > D > B > C

(c) B>C >D>E >A (d) None of the above.
15. When 2, 2, 6, 6-tetramethylcyclohexanol is reacted with acid, which of the following compounds would
be expected to be found in the reaction mixture?

(a) (b)

(c) (d)

CH3

16. Product of the reaction, H3C C CH2 OH HCl would be:

CH3
CH3 Cl

(a) H3C C CH2 Cl (b)

H3C CH3
CH3
CH3 H3C

(c) H3C C CH2 CH3 (d) CH CH CH3

Cl H3C Cl
 Chemistry : Alcohols, Ethers and Phenols


H 1. B2 H 6 1. O3
17. C7 H14 O(X)  C 7 H12   C 7 H14O(Z)  
 2. H O / OH – 2 2
2. Zn / H 2 O
(A3 alcohol) (Y) (An isomer of X)

O
CH3
CH3
(a) OH (b)
OH
CH3
CH3
CH3

(c) (d)
HO CH3
OH
18. Which of the following does not react with aqueous periodic acid:
H2 C OH
H2 C OH
C O
(a) (b)
H2 C OH
H2 C OH

H2 C OH H2 C OH

CH2 HC OH
(c) (d)
H2 C OH H2 C OH

CH 3 MgBr (execess)
19. (C 2 H5 O) 2 CO  H 3 O
 A
A can be:
CH3 CH3

(a) H5 C 2 C OH (b) H5 C2 C OH

C 2 H5 CH3

CH3

(c) H5C 2 C OH (d) (CH3 ) 3 C — OH

H
Chemistry : Alcohols, Ethers and Phenols

20. Which is dehydrated to maximum extent using conc. H2SO4?

O
O
OH
(a) (b)

OH

O O
CH3
(c) (d)
OH OH
 Chemistry : Alcohols, Ethers and Phenols

SECTION - III
MULTIPLE CHOICE QUESTIONS
1. Propan-l-ol can not be prepared from propene by
(a) H2O/H2 SO 4 (b) Hg(OAc)2/H2O followed by NaBH4
(c) B2H6 followed by H2O2 (d) CH3CO2 H/H2 SO 4
2. Alcohols may act as –
(a) Oxidising agent (b) Reducing agent
(c) Lewis base (d) Bronsted acid
3. The reagents used for the ring alkylation of phenol are –
(a) C2H5Cl and anhyd AlCl3 (b) CH3CH=CH2 and H2SO4
(c) (CH3 )2CHOH and H2SO4 (d) CH3CH=CH2 and HF
4. Which of the following is the most reactive with HCl in the presence of ZnCl2?
(a) (Me2 CH)3 COH (b) (Me2 CH)2 CHOH
(c) Me2CH – CH2OH (d) C6 H5 OH
5. Which of the following compounds yield 1-methyl cyclohexanol by normal hydration process?
CH2 CH3

(a) (b)

CH3

(c) (d) None of the above

6. Chromic anhydride in H2SO4 is turned blue by

(a) primary alcohol (b) secondary alcohol

(c) tertiary alcohol (d) OH

7. Which of the following compounds are easily oxidized by K2Cr2O7 and H2SO4?
(a) CH3 CH 2 OH (b) (CH3) 2CHOH
(c) CH3 CHO (d) (CH3 )3 COH
8. Which of the following reactions are used in the preparation of alcohols?
LiAlH 4
(a) C 2 H5 Br  aq. KOH 
 (b) (CH 3 ) 2 C  O 
Na / EtOH H 2O
(c) CH3  COOCH 3   (d) (CH 3 ) 2 CHBr  
9. Alcohols can be prepared from alkenes by
(a) Hydration (b) Hydroboration
(c) Oxymercuration (d) none of these
10. When glycerol is heated with an excess of HI, it produces
(a) allyl iodide (b) propene
(c) glycerol tri iodide (d) 2-iodopropane
Chemistry : Alcohols, Ethers and Phenols

MISCELLANEOUS QUESTIONS
SECTION - IV
COMPREHENSION TYPE QUESTIONS
Write up - I
In a polyhydric alcohol, the total numbers of hydroxyl groups are estimated by the following methods :
(i) A known mass of the acetyl derivative of polyhydric alcohol is taken. It is mixed with an excess
volume of a standard alkali solution. Both are refluxed. Alkali is used in the hydrolysis of acetyl
derivative. The unused alkali is measured by doing titration with a standard acid solution and total
number of hydroxyl groups (n) can thus be calculated stoichiometrically.
CH3COCl nKOH
A(OH) n   A(OCOCH3 )   A(OH) n )  nCH3COOK
Polyhydric Acetyl derivative
alcohol

(ii) Total number of —OH groups in vicinal position can be calculated by periodic acid or lead tetra
acetate oxidation.

CH3 CH3

C OH C O
HIO4

or Pb(COCOCH 3 ) 4


C OH C O

1. 0.436 of acetyl derivative of a polyhydric alcohol (molecular mass = 92) require 0.336 g KOH for
hydrolysis. The total numbers of hydroxyl group(s) in the alcohol are
(a) 1 (b) 2
(c) 3 (d) 4
2. The ratio of the number of moles of lead tetra acetate required for the oxidation of 1 mole of
glucose to that of 1 mole of fructose is
(a) 1 : 1 (b) 2 : 1
(c) 5 : 4 (d) 4 : 5
3. When 1 mole of glucose is oxidized by periodic acid, the product(s) formed are
(a) 4 moles of formic acid and 1 mole of formaldehyde
(b) 5 moles of formic acid and 1 mole of formaldehyde
(c) 3 moles of formic acid and 2 moles of formaldehyde
(d) 2 moles of formic acid and 4 moles of formaldehyde
 Chemistry : Alcohols, Ethers and Phenols

Write up - II
Both symmetrical and unsymmetrical ethers can by prepared by Williamson’s synthesis which involves
the reaction between an alkyl halide and an alkoxide ion. The reaction occurs by SN2 mechanism.
Therefore, for good yields of ethers, the alkyl halide must be primary while the alkoxide may be
derived from 1°, 2° or 3° alcohols. Since 2° and 3° alkyl halides prefer to undergo elimination rather
than substitution reactions, therefore, they are not suitable starting materials in Williamson’s synthesis.
Likewise, vinyl and aryl halides being unreactive do not undergo Williamson’s synthesis. The reverse
process involving the cleavage of ethers to give back the original alkyl halide and the alcohol can be
carried out by heating the ether with HI at 373 K. If one group is methyl and the other is a 1° or a
2° alkyl group, the reaction occurs by SN2 mechanism. Because of steric hindrance, the I– ion attacks
the smaller alkyl group leading to the formation of methyl iodide and the alcohol derived from the
bulkier alkyl group. If, however, one group is methyl and the other is a tert–alkyl group, the reaction
occurs by SN1 mechanism and the alkyl halide is derived from the more stable carbocation

4. Which of the following reagents when heated will give a good yield of an ether
(a) Isopropyl bromide and sodium isopropoxide (b) Isopropyl bromide and sodium ethoxide
(c) Bromobenzene and sodium phenoxide (d) Sodium tert-butoxide and ethyl bromide
5. Which of the following ethers can be prepared by Williamson's synthesis?
(a) Benzyl methyl ether (b) Methyl vinyl ether
(c) Divinyl ether (d) Diphenyl ether
6. Benzyl ethyl ether reacts with HI to form
(a) p-Iodotoluene and ethyl alcohol (b) Benzyl alcohol and ethyl iodide
(c) Benzyl iodide and ethyl alcohol (d) Iodobenzene and ethyl alcohol

MATCHING TYPE QUESTIONS

7. Match the following
Column – A Column – B (Relative reactivity)
(A) H— 1. 0.1
(B) CH 3 — 2. 3
(C) C 2 H5 — 3. 1
CH3
(D) CH CH3 4. 100
CH 3

(A) (B) (C) (D)

(a) 4 2 3 1
(b) 4 2 1 3
(c) 2 4 3 1
(d) 1 2 3 4
Chemistry : Alcohols, Ethers and Phenols

8. Match the following

Column - A Column – B

(A) CH3  O  SO 2CH 3  C2 H5 O 1. CH3  CH 2  PH 2

(B) CH3  CH 2  I  PH 3 2. CH3  O  C 2 H 5

 
(C) HC  C Na  CH 3CH 2 Br 3. CH3  O  CH 3


(D) CH3  Cl  CH 3  O 4. CH  C  CH 2  CH 3

(A) (B) (C) (D)

(a) 4 3 2 1
(b) 1 2 3 4
(c) 2 1 4 3
(d) 2 1 3 4

ASSERTION-REASON TYPE QUESTIONS

The question given below consist of an ASSERTION and the REASON. Use the following key for the
appropriate answers
(a) If both Assertion and Reason are correct and Reason is the correct explanation for Assertion
(b) If both Assertion and Reason are correct and Reason is not the correct explanation for
Assertion
(c) If Assertion is correct but Reason is not correct.
(d) If Assertion is incorrect but Reason is correct.
9. Assertion : Boiling points of alcohols are higher than that of hydrocarbons.
Reason : Alcohols given higher intermolecular association of molecules.
10. Assertion : Acidic nature of alcohols follow the order 1° > 2° > 3°.
Reason : Acidic character of alcohols is due to the presence of polar O—H group.
11. Assertion : Anhydrous CaCl2 can be used for drying ethanol.
Reason : Sodium metal reacts with ethanol to form sodium ethoxide.
12. Assertion : Dipole moment of phenol is 1.54 D.
Reason : The dipole moment is due to the electron withdrawing effect of phenyl group which indirectly
influences —I effect of –OH group.
13. Assertion : tert-Butyl methyl ether on cleavage with HI at 373 K gives tert-butyl iodide and methanol.
Reason : The reaction occurs by SN2 mechanism.
14. Assertion : Grignard reagents are prepared in ethers but not in benzene.
Reason : Grignard reagents are soluble in benzene.
15. Assertion : Phenol is less acidic than p-nitrophenol.
Reason : Phenolate ion is more stable than p-nitrophenolate ion.
 Chemistry : Alcohols, Ethers and Phenols

SECTION - V
(PROBLEMS )

A. Only one option is correct (Objective Questions)

1. The structure of the intermediate I is

O Na O Na

CH2Cl CHCl2
(a) (b)

CH3 CH3

O Na O Na
CCl3 CH2OH
(c) (d)

CH3 CH3

2. The following compound on hydrolysis in aqueous acetone will give :

CH3 CH3 CH3
H3C O NO2
H Cl CH3

CH3 CH3 CH3

(K) H3C O NO2

H OH CH3

CH3 CH3 CH3

(L) H3C O NO2

OH H CH3

CH3 CH3 CH3

(M) H3C O NO2

H CH3 OH

(a) mixture of (K) and (L) (b) mixture of (K) and (M)
(c) only (M) (d) only (K)
Chemistry : Alcohols, Ethers and Phenols

3. When phenyl magnesium bromide reacts with t–butanol, the product would be :
(a) benzene (b) phenol
(c) t–butyl benzene (d) t–butyl phenyl ether
4. How many structures of F is possible?
CH3

H Br2 / CCl4
 [F]   C 4 H8 Br2
 H2 O  
H3C OH 5 such products
are possible
(a) 2 (b) 5
(c) 6 (d) 3
OH


5.  C 2 H 5 I 
OC H
2 5

Anhy. C H OH
2 5

(a) C6H5OC2H5 (b) C2H5OC2H5

(c) C6H5OC6H5 (d) C6H5I
6. 1–propanol and 2–propanol can be best distinguished by :
(a) oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(b) oxidation with acidic dichromate followed by reaction with Fehling solution
(c) oxidation by heating with copper followed by reaction with Fehling solution
(d) oxidation with concentrated H2SO4 followed by reaction with Fehling solution
7. The compound that will react most readily with NaOH to form methanol is :
(a) (CH3)4N+I– (b) CH3OCH3
(c) (CH3)3 S+I– (d) (CH3)3Cl
8. Assertion : Phenol is more reactive than benzene towards electrophilic substitution reaction.
Reason : In the case of phenol, the intermediate carbocation is more resonance stabilized.
(a) both assertion and reason are correct and reason is the correct explanation of the assertion
(b) both assertion and reason are correct, but reason is not the correct explanation of the assertion
(c) assertion is correct, but reason is incorrect
(d) assertion is incorrect, but reason is correct
9. Benzene diazonium chloride on reaction with phenol in weakly basic medium gives :
(a) diphenyl ether (b) p–hydroxyl azobenzene
(c) chlorobenzene (d) benzene
10. (CH3)3C Mg Cl on reaction with D2O produces :
(a) (CH3)3CD (b) (CH3)3COD
(c) (CD)3CD (d) (CD)3COD
 Chemistry : Alcohols, Ethers and Phenols

11. In the following compounds.

The order of acidity is :
OH OH OH OH

NO2
CH3 NO2
I II III IV

(a) III > IV > I > II (b) I > IV > III > II
(c) II > I > III > IV (d) IV > III > I > II
12. The products of combustion of an aliphatic thiol (RSH) at 298 K are :
(a) CO2(g), H2O(g) and SO2(g) (b) CO2(g), H2O(l) and SO2(g)
(c) CO2(l), H2O(l) and SO2(g) (d) CO2(g), H2O(l) and SO2(l)
13. Assertion : p–nitrophenol is a stronger acid than o–nitrophenol.
Statement : Intramolecular hydrogen bonding make the o–isomer weaker than the p–isomer.

(a) both assertion and statement are true and statement is the correct explanation of assertion
(b) assertion is correct and statement is wrong, statement is not the correct explanation of assertion
(c) assertion is wrong and statement is correct, statement is not the correct explanation of assertion
(d) both assertion and statement are wrong and statement is not the correct explanation of assertion.
14. In CH3CH2OH, the bond that undergoes heterolytic cleavage most readily is :
(a) C–C (b) C–O
(c) C–H (d) O–H
15. Phenol reacts with bromine in carbon disulphide at low temperature to give :
(a) m–bromophenol (b) o–and p–bromophenol
(c) p–bromophenol (d) 2, 4, 6–tribromophenol
16. Statement (S):Solubility of n–alcohol in water decreases with increase in molecular weight.
Explanation (E) : The reactive proportion of the hydrocarbon part in alcohols increases with increasing
molecular weight which permits enhanced hydrogen bonding with water.
(a) both (S) and (E) are correct and (E) is the correct explanation of (S)
(b) both (S) and (E) are correct but (E) is not the correct explanation of (S)
(c) (S) is correct but (E) is wrong
(d) (S) is wrong but (E) is correct
17. Hydrogen bonding is maximum in :
(a) ethanol (b) diethyl ether
(c) ethyl chloride (d) triethyl amine
Chemistry : Alcohols, Ethers and Phenols

18. HBr reacts fastest with :

(a) 2–methyl propan–2–ol (b) propan–1–ol
(c) propan–2–ol (d) 2–methyl propan–1–ol
19. An industrial method of preparation of methanol is :
(a) catalytic reduction of carbon monoxide in presence of ZnO–Cr2O3
(b) by reacting methane with steam at 900°C with a nickel catalyst
(c) by reducing formaldehyde with LiAlH4
(d) by reacting formaldehyde with aqueous sodium hydroxide solution
20. When phenol is treated with excess bromine water, it gives :
(a) m–bromophenol (b) o–and p–bromophenol
(c) 2, 4–dibromophenol (d) 2, 4, 6–tribromophenol

B. More than one options are correct (Objective Questions)

1. Phenol is less acidic than :

(a) acetic acid (b) p–methoxyphenol
(c) p–nitrophenol (d) ethanol
2. When phenol is reacted with CHCl3 and NaOH followed by acidification, salicylaldehyde is obtained.
Which of the following species are involved in the above mentioned reaction as intermediates?

O OH
H CHCl2

(a) CCl2 (b)

-
O O
H CHCl2

(c) CHCl (d)

OH

3. The ether O CH2 when treated with HI produces :

(a) CH2 I (b) CH2 OH

(c) I (d) OH
 Chemistry : Alcohols, Ethers and Phenols

SUBJECTIVE QUESTIONS
1. An optically active alcohol A (C­6H10O) absorbs two moles of hydrogen per mole of A upon catalytic
hydrogenation and gives a product B. The compound B is resistant to oxidation by CrO3 and does not
show any optical activity. Deduce the structure of A and B.

2. 2, 2–dimethyloxirane can be cleaved by acid (H+). Write mechanism.

3. Although phenoxide ion has more number of resonating structures than benzoate ion, benzoic acid is a
stronger acid than phenol. Why?
4. Give reasons for the following in one or two sentences.
“Acid catalysed dehydration of t–butanol is faster than that of n–butanol.
5. An ester A(C4H8O2), on treatment with excess methyl magnesium chloride followed by acidification,
gives an alcohol B as the sole organic product. Alcohol B, on oxidation with NaOCl followed by
acidification, gives acetic acid. Deduce the structures of A and B. Show the reactions involved.

6. Each of the following reactions gives two products. Write the structures of the products :
Alc. KOH, heat
(i) C6 H5 CH 2 CHClC 6 H5   
HI (excess)
(ii) (CH 3 ) 2 CHOCH 3  heat
 
7. Complete the following reactions with appropriate structures of products/reagents :

O
O CHC6 H5
(i) LiAlH 4
[A]
 
(ii) H  heat
[B]

8. Explain briefly the formation of the products giving the structures of the intermediates.
H2 C
CH CH2 CH CH2
HCl +
  CH CH2 Cl etc
(a) CH CH2 OH CH2 CH2 Cl
2
H2 C

CH3 CH3

CH CH CH CH
HCl

 only
CH2 CH2 OH CH2 CH2 Cl

NaNH 2
(b) OCH3 
NH 3
 OCH3

Br H2 N
Chemistry : Alcohols, Ethers and Phenols

9. What would be the major product in each of the following reactions :

F

CH3
| NaOCH 3
(i) C2 H5 OH
CH3 —C — CH 2 Br   (ii) 


|
CH3
NO2
10. Identify A, B and C and give their structures :
O
CH3
CH3

Br2 

NaOH
 A  B 

C(C 7 H12 O)

O
11. How would you synthesis 4–methoxyphenol from bromobenzene in NOT more than five steps? State
clearly the reagents used in each step and show the structures of the intermediate compounds in your
synthetic scheme.
12. Convert,
OH


 Aspirin

13. H3C CH2

OH
Write resonance structure of the given compound.
Cl


KCN C2 H 5 ONa / C2 H5 OH H3O SOCl 2
14.  (A)  (B)  (C)  (D)
DMF C H CHO / 
6 5  CH NH 3 2

Identify A to D.

O
OH


H / 1.O3 NaOH
15.   X   Y  
2. Zn / CH COOH
3

Identify X and Y.
 Chemistry : Alcohols, Ethers and Phenols

ANSWERS

EXERCISE - 1
(a) 2 phenyl-2-propanol (b) 5-bromo-2-heptanol
(c) 4-methyl cyclohex-3-ene-1-ol

EXERCISE - 2
O CH2 OH
H3O+
MgBr  H2 C CH2

[O] O

(i) CH3MgBr

(ii) H3O+
O OH

CH3 CH3

EXERCISE - 3
Ni / H
(a) H3C COOH 
2
 H3C CH2 OH

O OH

(b) H3C C NaBH 4

COOH   H3C CH COOH

O O

(c) H C C LiAlH 4
OCH3   HO CH2 CH2 OH

EXERCISE - 4
Cl

(i) CH2 Cl (ii) CH CH CH3

CH3
Chemistry : Alcohols, Ethers and Phenols

EXERCISE - 5

CH2
OH conc.
(i)  H3C
H 2SO 4
n Hg(OAC) 2
H 2O
NaBH 4
CH3
conc.
CH3 
H 2SO 4
 H3C
H3C
OH
Br2

Br
CH3
NaNH 2
CH3  H3C
H3C

Br

(ii) H3 C
PCC nCH CH CH MgBr H O 
OH   H3C CHO 
3 2 2 3


CH3
conc.
CH3  H3C
H 2SO4
H3C
OH

O O OH
CH3 MgBr (excess)
OH
(iii) 
 H 3O 

EXERCISE - 6
HCHO  2HCOOH  CO 2  CH 3 — CHO
 Chemistry : Alcohols, Ethers and Phenols

EXERCISE - 7

Me Me

Me C OH + CH3I Me C I + CH3OH

Me Me

(A) (B)

EXERCISE – 8

O2 N Me O 2N Me

H
C   C
Me2 N O OH Me2N O OH2

O 2N Me
C
H O O NMe2   O2 N
H2 O :
Me
C
H
O NMe2

CH3 O

O 2N C O NMe2 O 2N C Me

O H
HO NMe2

EXERCISE – 9
OH OH
OH
CHO MgBr
CHCl3
  HO CH
NaOH
H 3O 
Chemistry : Alcohols, Ethers and Phenols

EXERCISE – 10
HO CH3 HO CH3 HO CH3 OH OH
CH3 CH3

H
  
 
 H 

H3C H3C H3C H3C H3C
O OH OH OH OH

SECTION - I
(Subjective Questions)

Answers are given in the separate booklet (Level – I to Level – III)

SECTION - II
(Single Choice Questions)
1. (b) 2. (a)
3. (a) 4. (d)
5. (a) 6. (d)
7. (c) 8. (c)
9. (c) 10. (b)
11. (a) 12. (b)
13. (b) 14. (a)
15. (d) 16. (c)
17. (b) 18. (c)
19. (d) 20. (d)

SECTION - III
(Multiple Choice Questions)
1. (a, b, d) 2. (c, d)
3. (b, c, d) 4. (a)
5. (b) 6. (a, b, d)
7. (a, b, c) 8. (a, b, c, d)
9. (a, b, c) 10. (d)
 Chemistry : Alcohols, Ethers and Phenols

SECTION - IV
(Comprehension Type Questions)
1. (c) 2. (a)
3. (b) 4. (a)
5. (a, b, c, d) 6. (b, c)

(Multiple Matching Type Questions)

7. (a) 8. (c)

(Assertion Reason Type Questions)

9. (a) 10. (b)
11. (c) 12. (c)
13. (c) 14. (c)
15. (c)

SECTION - V

A. Only one option is correct (Objective Questions)

1. (b) 2. (a)
3. (a) 4. (b)
5. (b) 6. (c)
7. (a) 8. (c)
9. (b) 10. (a)
11. (d) 12. (b)
13. (a) 14. (d)
15. (b) 16. (c)
17. (a) 18. (a)
19. (a) 20. (d)

B. More than one options are correct (Objective Questions)

1. (a, c) 2. (a, d)
3. (a, d)

SUBJECTIVE
Answers are given in the separate booklet.