ARUL INSTITUTE, CHENNAI

7200642647 / 7200442647

+2 CBSE – CHEMISTRY – TEST CODE (CC3)

ALCOHOLS, PHENOLS & ETHERS

TIME : 3 HOURS MAXIMUM MARKS : 70

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GENERAL INSTRUCTIONS :

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(a) There are 33 questions in the question paper. All questions are compulsory.

(b)
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Section A: Q.No. 1 to 16 are objective type questions. Q. No. 1 and 2 are passage based questions

carrying 4 marks each while Q. No. 3 to 16 carry 1 mark each.

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(c) Section B: Q.No. 17 to 25 are short answer questions and carry 2 marks each.
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(d) Section C: Q.No. 26 to 30 are also short answer questions and carry 3 marks each.

(e) Section D: Q.No. 31 to 33 are long answer questions and carry 5 marks each.
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(f) Use of calculators and log tables is not permitted.

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SECTION – A

1. Read the given passage and answer the following questions: (1 x 4 = 4)

A compound (X) containing C, H and O is unreactive towards sodium. It also does not react with

Schiff’s reagent. On refluxing with an excess of HI, (X) yields only one organic product (Y). On

hydrolysis, (Y) yields a new compound (Z) which can be converted into (Y) by reaction with P

and I2. The compound (Z) on oxidation with KMnO4 gives a carboxylic acid. The equivalent

weight of the acid is 60.

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 1. The compound (X) is an

(a) acid (b) aldehyde (c) alcohol (d) ether

2. The IUPAC name of the acid formed is

(a) methanoic acid (b) ethanoic acid (c) propanoic acid (d) butanoic acid

3. Compound (Y) is

(a) ethyl iodide (b) methyl iodide (c) propyl iodide (d) mixture of (a) & (b)

4. Compound (Z) is

(a) methanol (b) ethanol (c) propanol (d) butanol

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2. Read the given passage and answer the following questions: (1 × 4 = 4)

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Williamson’s synthesis is used for the preparation of symmetrical as well as unsymmetrical
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ethers. It follows bimolecular nucleophilic substitution reaction mechanism. In Williamson’s

synthesis, primary alkyl halide is used for preparation of ethers because secondary and tertiary
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alkyl halide give alkene. Ethers are cleaved by hydrogen halides to alcohol and alkyl halide
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where alkyl halide is corresponding to that alkyl group which has a smaller number of carbon

atom (it is because of less steric hindrance). In polar media unsymmetrical ether like tertiary
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butyl ethyl ether gives ethyl alcohol and tertiary butyl halide as reaction proceeds via
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carbocation.

In these questions (i) – (iv), a statement of assertion followed by a statement of reason is given.

Choose the correct answer out of the following choices.

(A) Assertion and reason both are correct statements and reason is correct explanation for

assertion.

(B) Assertion and reason both are correct statements but reason is not correct explanation for

assertion.
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 (C) Assertion is correct statement, but reason is wrong statement.

(D) Assertion is wrong statement, but reason is correct statement.

(i) Assertion : Rate of reaction of alkyl halide in Williamson’s synthesis reaction is

primary RX > secondary RX > tertiary RX

Reason : It is a type of bimolecular nucleophilic substitution reaction

(ii) Assertion : t-butyl methyl ether is not prepared by the reaction of t-butyl bromide with

sodium methoxide

Reason : Sodium methoxide is a weak nucleophile

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(iii) Assertion : Williamson’s synthesis method cannot be used for preparing diphenyl ether

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Reason : Aryl halides do not undergo nucleophilic substitution easily
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(iv) Assertion : When isopropyl bromide is treated with sodium isopropoxide, di isopropyl

ether is obtained as a major product

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Reason : With secondary alkyl halides, both substitution and elimination occur
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Following questions 3 to 11 are multiple choice questions carrying 1 mark each:

3. Which one of the following is most acidic?

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(a) phenol (b) p-cresol (c) p-nitrophenol (d) catechol

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4. Which one of the following is least reactive towards aromatic electrophilic substitution reaction?

(a) phenol (b) 2-nitrophenol (c) 4-nitrophenol (d) 2,4,6-trinitrophenol

5. 1-ethoxy-2-methylpropane on treatment with HI produces

(a) 2-methyl propane & ethanol (b) 2-methyl-1-propanol & ethane

(c) 2-methyl-1-propanol & iodoethane (d) 1-iodo-2-methyl propane & ethanol

6. The most suitable reagent for converting a primary alcohol to an aldehyde is

(a) KMnO4 (b) PCC (c) K2Cr2O7 (d) CrO3

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7. Amongst the following alcohols, the one that would react most readily with con.HCl & ZnCl2 is

(a) 1-butanol (b) 2-butanol

(c) 2-methyl-1-propanol (d) 2-methyl-2-propanol

8. Which one of the following reactions does not involve formation of C–C bond?

(a) Wurtz reaction (b) Cannizaro reaction

(c) Riemer-Tiemann reaction (d) Kolbe’s reaction

9. Which one of the following reaction follows anti-Markovnikov’s type addition?

(a) hydration (b) hydroboration-oxidation

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(c) oxymercuration-demercuration (d) both (b) & (c)

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10. Which one of the following does not undergo iodoform reaction?
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(a) methyl alcohol (b) ethyl alcohol (c) isopropyl alcohol (d) acetone

11. Which one of the following can be used to distinguish between phenol and benzoic acid?
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(a) neutral FeCl3 (b) aqueous NaOH (c) Tollen’s reagent (d) Molisch reagent
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In the following questions (12 to 16), a statement of assertion followed by a statement of reason is

given. Choose the correct answer out of the following choices.

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(A) Assertion and reason both are correct statements and reason is correct explanation for assertion.
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(B) Assertion and reason both are correct statements but reason is not correct explanation for

assertion.

(C) Assertion is correct statement, but reason is wrong statement.

(D) Assertion is wrong statement, but reason is correct statement.

12. Assertion : The ease of dehydration of alcohols follows the order:

primary > secondary > tertiary

Reason : Dehydration proceeds through the formation of carbocations

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13. Assertion : o-nitrophenol is more volatile than p-nitrophenol

Reason : Intramolecular hydrogen bonding is present in o-nitrophenol while

intermolecular H-bonding is in p-nitro phenol

14. Assertion : Phenol is less acidic than p-nitrophenol

Reason : Phenolate ion is more stable than p-nitrophenolate ion

15. Assertion : Solubility of alcohols decreases with increase in size of alkyl/aryl groups

Reason : Alcohols form H-bonding with water to show soluble nature

16. Assertion : Primary and secondary alcohols can be distinguished by Victor-Meyer’s test

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Reason : Primary alcohols form nitrolic acid which dissolves in NaOH to form blood red

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colouration but secondary alcohols form pseudonitrols which give blue
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colouration with NaOH
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SECTION – B
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(Q17 – Q25 are Short Answer Type and carry 2 marks each)

17. Explain why phenols are more acidic than alcohols?

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18. Why 1-butanol has higher boiling point than 2-methyl-1-propanol?

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19. How will you convert ethanol to diethyl ether?

20. How will you distinguish between cresol and benzoic acid?

21. Give an example for Riemer-Tiemann reaction.

22. Explain why o-nitrophenol has lower boiling point than p-nitrophenol?

23. Draw the structure of hex-1-en-3-ol.

24. Explain why C–O bond length in phenols is shorter than C–O bond length in alcohols?

25. Write the equation involved in the conversion of phenol to salicylic acid.

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 SECTION – C

(Q26 – Q30 are Short Answer Type II carrying 3 marks each)

26. How will you bring about the following conversions?

(a) phenol to benzene (b) but-2-ene to ethanol

27. Write about Kolbe’s reaction giving a suitable example.

28. Write the mechanism for dehydration of ethanol to ethene.

29. Name the reagents used in the following reactions:

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(a) Friedel Crafts acylation of anisole

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(b) Oxidation of unsaturated alcohol to unsaturated aldehyde

30. Give reason for the following:

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(a) alcohols are more soluble in water than hydrocarbons of comparable molar mass
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(b) o-nitrophenol is more acidic than o-methoxyphenol
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SECTION – D
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(Q31 – Q33 are Long Answer Type carry 5 marks each)

31. (a) How are the following compounds obtained from phenol? (a) picric acid (b) benzoquinone.
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(b) Explain how primary, secondary and tertiary alcohols can be distinguished using Lucas test?

(c) How will you prepare ethoxybenzene & 2-methoxypropane using Williamson’s ether

synthesis?

32. (a) Why ether is preferentially used as a solvent in organic reactions?

(b) Why anisole undergoes electrophilic substitution at a faster rate than benzene?

(c) Explain the coupling reaction of phenol.

+2/CBSE/Chemistry/2021–2022/CC3 Arul Institute
 (d) Give an example (each) for dehydrogenation of alcohols and hydration of alkenes.

(e) t-butyl chloride cannot be used as a substrate for preparing ethers using Williamson’s ether

synthesis.

33. (a) What happens when methyl isobutyl ether is treated with HI?

(b) Explain the action of chlorine on diethyl ether in the presence of light.

(c) Acid catalysed dehydration of tertiary butyl alcohol is faster than n-butyl alcohol. Justify.

(d) How will you convert aniline to phenol and phenol to aniline?

(e) Explain iodoform test using a suitable alcohol.

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