SRINIVASA RAMANUJAN PUBLIC SCHOOL, PRAYAGRAJ

TEST SHEET
Class – XII
Subject – Chemistry
TOPIC – Alcohols, Phenols and Ethers
Name of the Student: __________________________ Roll No. - ____ Max Time: 01 Hr.

Q1. Multiple Choice Questions

1. Arrange the following compound in decreasing order of boiling point

(i) propan-1-ol
(ii) butane-1-ol
(iii) butan-2-ol
(iv) pentan-1-ol
a) i > iii > ii > iv
b) i > ii > iii > iv
c) iv > iii > ii > i
d) iv > ii > iii > i
2. What is the correct order of reactivity of alcohols in the following reaction?
R—OH + CHCl Zn,dust R—Cl + H2O
a) 1° > 2° > 3°
b) 1° < 2° > 3°
c) 3° > 2° > 1°
d) 3° > 1° > 2°
3. IUPAC name of the compound CH3—CH2—O—CH3 is:
a) 1-methoxy-1-methyl ethane
b) 2-methoxy-2-methyl ethane
c) 2-methoxy ethane
d) isopropylmethyl ether
4. The major product obtained on interactionof phenol with NaOH and CO2 is
a) Benzoic acid
b) Salicaldehyde
c) Salicylic acid
d) Pthalic acid
5. Iodoform canbe prepared from all except
a) butan-2-one
b) acetophenone
c) propan-2-ol
d) propan-1-ol
6. Which of the following alcohol on dehydration with conc H2SO4 gives but-2- enc?
 a) 2-methylpropan-2-ol
b) Butan-1-ol
c) 2-methyl propan-1-ol
d) Butan-2-ol
7. Which of the following is a weaker acid than phenol?
a) 4-Methoxy phenol
b) 3, 5-dinitrophenol
c) 4-Methyl phenol
d) 4-Nitrophenol
8. Which reagents can not be used to oxidise primary alcohols to aldehydes?
a) Acidic KMnO4
b) Anhydrous CrO3
c) Both (a) and (b)
d) None of the above

9. Name a reagent that can be used to oxidise alcohol to aldehyde?

a) NaBH4
b) LiAlH4
c) PCC
d) None of the above
10. Which of the following compound has two hydroxyl groups?
a) Picric acid
b) o- Cressol
c) Both (a) and (b)
d) None of the above
11. What happens when phenol is treated with dihydrogen in the presence of the nickel
catalyst?
a) Benzene
b) Cyclo hexanol
c) Toluene
d) None of the above
12. Lucas reagent is the mixture of
a) Concentrated Hydrochloric acid and anhydrous zinc chloride
b) Concentrated Nitric acid and anhydrous zinc chloride
c) Concentrated Hydrochloric acid and hydrous zinc chloride
d) Concentrated Nitric acid and hydrous zinc chloride
13. Phenol is less acidic than
a) p-nitro phenol
b) acetic acid
 c) Both (a) and (b)
d) None of the above
14. Phenol reacts with the excess of bromine to yield
a) Meta Bromo phenol
b) Ortho and Para Bromo phenol
c) 2, 4, 6- tribromo phenol
d) None of the above
15. Dehydration of alcohol is an example of
a) Elimination reaction
b) Addition reaction
c) Substitution reaction
d) None of the above
Q2. Assertion Reason Type Questions
The question given below consist of an Assertion and the Reason.
a) If both assertion and reason are CORRECT and reason is the CORRECT
explanation of the assertion.
b) If both assertion and reason are CORRECT, but reason is NOT the CORRECT
explanation of the assertion.
c) If assertion is CORRECT but reason is INCORRECT.
d) If assertion is INCORRECT but reason is CORRECT.
e) If both assertion and reason are INCORRECT.
1. Assertion: The boiling point of alcohol is higher than those of hydrocarbons of
comparable moleculal mass.
Reason: Alcohol show intramolecular hydrogen banding.
2. Assertion: O and p-nitrophenols can be separated by steam distillation. Reason: O-
isomeris steamvolatile due to chelation and p-isomer is not steam volatile due to
intermolecular hydrogen bonding.
Q3. Match the column
A. Methanol and ethanol P. lucas reagent
B. Phenol and cyclohexanol Q. Sodium metal
C. n-propylalcohol and tertbutyl alcohol R. Iodoformtest
D. Methanol and diethylether S. Ferric chloride
a) A–Q, B–S, C–P, D–R
b) A–S, B–P, C–Q, D–R
c) A–P, B–Q, C–R, D–S
d) A–R, B–S, C–P, D–Q
Q4. Match the column
 A. Willionsan synthesis P. Conversion of phenol to salicylic acid
B. Conversion of 2° alcohol to ketone Q. Conversion of phenol to salicaldehyde
C. Reimer Tiemann reaction R. Heated with Cu-573k.
D. Kolbc's reaction S. reaction of alkyl halide with sodium
alkoxide
a) A–S, B–R, C–Q, D–P
b) A–R, B–S, C–Q, D–P
c) A–R, B–Q, C–P, D–S
d) A–Q, B–P, C–R, D–S
Q5. Very short answer type questions
1. How is phenol obtained from aniline?
2. Why phenol is acidic in nature?
3. Among HI, HBr and HCl, HI is most reactive towards alcohols. Why?
4. Name a compound which is used as antiseptic as well as disinfectant.
5. What is nitrating mixture ?
6. Lower alcohols are soluble in water, higher alcohols are not. Why ?
7. What happens when CH3 CH2 OH heated with red P and HI ?
8. Ethanol has higher boiling point than methoxy methane. Give reason.
9. How could you convert ethanol to ethene ?
10. Explain Kolbe’s reaction with example.
11. Which of the following isomer is more volatile :
o-nitrophenol or p-nitrophenol
Q4. Short answer type questions
1. Write one chemical reaction to illustrate the following :
(i) Reimer-Teimann reaction
(ii) Williamson’s synthesis
2. Account for the following :
(i) Phenol has a smaller dipole moment than methanol.
(ii) Phenol goes electrophilic substitution reactions.
3. Complete the following equations and name the products :
(i) Phenol + FeCl3 →
(ii) C6H5OH + CHCl3 + NaOH →
(iii) C6H5OH + Br2 (aq) →
4. Write :
(i) Friedel-Crafts reaction
(ii) Coupling reaction
5. Give one reaction of alcohol involving cleavage of :
 (i) C – O bond
(ii) O – H bond
6. Etherial solution of an organic compound ‘X’ when heated with Mg gave ‘Y’. ‘Y’ on
treatment with CH3 CHO followed by acid hydrolysis gave 2-propanol. Identify the
compound ‘X’. What is ‘Y’ known as ?
7. While separating a mixture of o- and p-nitrophenols by steam distillation name the
isomer which is steam volatile. Give reason.
8. Account for the following :
(i) Phenol has a smaller dipole moment than CH3OH.
(ii) Phenol do not give protonation reactions readily.
9. Write the reactions and conditions involved in the conversion of :
(i) Propene to propan-2-ol.
(ii) Phenol to salicylic acid.
10. Write mechanism of reaction of HI with methoxymethane.
11. Arrange in order of boiling points :
(i) C2 H5 – O – C2 H5 , C4 H9 COOH, C4 H9 OH
(ii) C3 H7 CHO, CH3 COC2 H5 , C2 H5 COOCH3 , (CH3 CO)2 O
12. Which of the following is an appropriate set of reactants for the preparation of 1-
methoxy-4-nitrobenzene and why ?
13. Ethers are relatively inert. Justify
14. How will you distinguish between CH3 OH and C2 H5 OH ?
15. Name the reagents which are used in the following conversions :
(i) 1º alcohol to an aldehyde
(ii) Butan-2-one to butan-2-ol
(iii) Phenol to 2, 4, 6 tribromophenol
16. Write structures of the major products of the following :
(i) Mononitration of 3-methylphenol
(ii) Dinitration of 3-methylphenol
(iii) Mononitration of phenyl ethanoate
17. Give equations of the following reactions :
(i) Oxidation of propan-1-ol with alkaline KMnO4 solution.
(ii) Bromine in CS2 with phenol.
(iii) Treating phenol with chloroform in presence of aqueous NaOH
 18. Describe the following reactions with examples :
(i) Reimer-Teimann reaction
(ii) Kolbe’s reaction
(iii) Friedel Crafts acylation of anisole
19. How will you convert :
(i) Phenol to cyclohexanol
(ii) Benzyl chloride to benzyl alcohol
(iii) Anisole to phenol
20. Dehydration of alcohols to form an alkene is always carried out with conc. H2 SO4 and
not with conc. HCl or HNO3 . Explain.

Q5. Long Answer type questions

1. An alcohol A (C4 H10O) on oxidation with acidified K2 Cr2 O7 gives carboxylic acid
‘B’ (C4 H8 O2 ). Compound ‘A’ when dehydrated with conc. H2 SO4 at 443 K gives
compound ‘C’ with aqueous H2 SO4 . ‘C’ gives compound ‘D’ (C4 H10O) which is an
isomer of ‘A’. Compound ‘D’ is resistant to oxidation but compound ‘A’ can be easily
oxidized. Identify A, B, C and D and write their structure.
2. An ether ‘A’ (C5 H12O) when heated with excess of hot concentrated HI 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. Deduce the structures of A, B, C, D and
E.
3. Phenol, C6 H5 OH when it first reacts with concentrated sulphuric acid, forms Y. The
compound, 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.
4. Give chemical tests to distinguish between compounds in each of the following pairs:

(i) Phenol and benzyl alcohol

(ii) Butan-2-ol and 2-methyl propan-2-ol
(iii) Phenol and alcohol

5. Arrange the following compounds in the increasing order of their acid strength.

4-nitrophenol, phenol, 2,4,6-trinitrophenol, 4-methylphenol

6. Give plausible explanation for each of the following:

(i) Ortho-nitrophenol is more acidic than ortho-methoxyphenol

(ii) Alcohols are easily protonated in comparison to phenols.
(iii) The relative ease of dehydration of alcohols is
tertiary˃secondary˃primary.
7. How would you obtain

(i) Benzoquinone from phenol.

(ii) Aspirin from Phenol