VELAMMAL NEW GEN SCHOOLS

CLASS: XII SESSION: 2023- 2024

UNIT TEST-2
(ALCOHOLS, PHENOLS & ETHERS)

CHEMISTRY (043)

Maximum Marks: 35 Time Allowed: 1.30 hours

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General Instructions:

 There are 18 questions in this question paper with internal choice.

The paper is divided into 5 Sections- A, B, C, D and E.
 SECTION A consists of 9 multiple -choice questions carrying 1 mark each.
 SECTION B consists of 4 short answer questions carrying 2 marks each.
 SECTION C consists of 3 short answer questions carrying 3 marks each.
 SECTION D consists of 1 case - based questions carrying 4 marks each.
 SECTION E consists of 1 long answer questions carrying 5 marks each.
 All questions are compulsory.
 Use of log tables and calculators is not allowed.
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Section – A 9*1=9

1. Which of the following alcohols gives 2-butene on dehydration by conc. H 2SO4?

Ans: (a) 2-methyl propene-2-ol

2. One mole of ethyl acetate on treatment with an excess of LiAlH 4 in dry ether
and subsequent acidification produces
Ans: (c) 2 moles of ethyl alcohol

3. Which of the following reagents cannot, be used to oxidise primary alcohols

to aldehydes?
Ans: (b) KMnO4 in acidic medium

4. 1-Phenylethanol can be prepared by the reaction of benzaldehyde with

Ans: (c) methyl iodide and magnesium

5. Which of the following alcohols will give the most stable carbocation during
dehydration?
Ans: (b) 2-methyl-2-propanol
6. A compound X with the molecular formula C3H8O can be oxidised to another
compound Y whose molecular formulae is C3H6O2. The compound X may be
Ans: (c) CH3CH2CH2OH
7. Order of esterification of alcohols are
Ans: (c) 1 ° > 2° > 3°

Assertion Reason Type Questions: In the following questions a statement of

assertion followed by a statement of reason is given. Choose the correct answer
out of the following choices.
(a) Both Assertion (A) and Reason(R) are true and R is correct explanation of A.
(b) Assertion and Reason are true but R is not the correct explanation of A.
(C) Assertion is true, Reason is false.
(D) Assertion is false, Reason is true.
8. Assertion: Addition reaction of water to but-1-ene in acidic medium yields
butan-2-ol
Reason: Addition of water in acidic medium proceeds through the formation
of primary carbocation.
Ans: (b) Assertion and Reason are true but R is not the correct explanation of A.

9. Assertion: p-nitrophenol is more acidic than phenol.

Reason: Nitro group helps in the stabilisation of the phenoxide ion by dispersal
of negative charge due to resonance.
Ans: (a) Both Assertion (A) and Reason(R) are true and R is correct explanation of A.
Section – B 4*2=8

10. How are the following conversions carried out?

(a) Propene to propan-2-ol

(b) Ethyl magnesium chloride to propan-1-ol.

11. Explain the following behaviours:

(a) Alcohols are more soluble in water than the hydrocarbons of comparable
molecular masses.
Ans: Due to presence of −OH group, alcohols can form hydrogen bonds with water but
hydrocarbons cannot form such hydrogen bonds due to the absence of −OH bonds..
Hence, alcohols are comparatively more soluble in water than hydrocarbons of comparable
molecular masses.
(b) Ortho-nitro phenol is more acidic than ortho-methoxyphenol.
Ans: In ortho nitro phenol, electron withdrawing nitro group is present in ortho position,
the electron density of O−H bond is reduced.
This makes removal of proton easy. After deprotonation, o-nitrophenoxide ion is resonance
stabilized. Hence, ortho nitrophenol is a stronger acid.
In ortho methoxyphenol, electron releasing methoxy group is present in ortho position, the electron
density of O−H bond is increased.
This makes removal of proton difficult. Hence, ortho methoxyphenol is less acidic.

12. Write the structures of the products when Butan-2-ol reacts with the following:
(a) CrO3 (b) SOCl2

13. Write the equation involved in the following reactions:

(a) Reimer - Tiemann reaction

(b) Williamson’s ether synthesis

Section – C 3*3=15

14. Explain the mechanism of acid catalysed hydration of an alkene to form

corresponding alcohol
Ans: There are three steps in the mechanism of acid catalysed hydration af an alkene to
form corresponding alcohol.

Step 1 : Carbocation formation and carbocation is formed by attack of H3O+.

Step 2 : Nucleophile H2O attacks on carbocation.

Step 3 : Deprotonation to form alcohol H+ will be eliminated.

15. Give reasons for the following :

(a) Phenol is more acidic than methanol.
Ans: Phenoxide ion is more stabilized than −CH3O ion through resonance.
Thus, phenol is more acidic than methanol.

(b) The C—O—H bond angle in alcohols is slightly less than the tetrahedral
angle (109°28′).
1. Ans: The C-O-H bond angle in alcohols is slightly less than the tetrahedral
angle because of the repulsion between the two lone pairs of electrons on
oxygen atoms (edited)
2. (c) (CH3)3C—O—CH3 on reaction with HI gives (CH3)3C—I and CH3—OH as the
main products and not (CH3)3C—OH and CH3—I.
Ans: Since, (CH3)3C+ is more stabilized through +I effect of three methyl
group thus (CH3)3C−I and CH3OH formed on treatment of HI with −(CH3)3
−CO−CH3.

16. (a) Give a seperate chemical test to distinguish between the following pairs
of compounds:
(i) Ethanol and Phenol
Ans: Litmus test : Phenols turn blue litmus red and alcohols have no
effect.
(ii) Methanol and Propan-2-ol.
Ans:
(b) Explain Kolbe’s reaction with the help of suitable example.

Section – D 1*4=4

Read the passage given below and answer the following questions:
17. Ethers are a class of organic compounds that contain an ether group—an oxygen
atom connected to two alkyl or aryl groups. They have the general formula R–O–R′,
where R and R′ represent the alkyl or aryl groups. Ether like water have a tetrahedral
geometry i.e. oxygen is sp3 hybridised. The C−O−C bond angle in ethers is slightly
greater than the tetrahedral angle due to repulsive interactions between the two
bulky groups when they are attached to oxygen. The following questions are multiple
choice questions. Choose the most appropriate answer:
(i) Which of the following cannot be made by using Williamson Synthesis:
Ans: (d) Di tert. butyl ether
(ii) The I.U.P.A.C. name of the ether CH2 = CH-CH2O CH3 is
Ans: (c) 3-Methoxy-l-propene
(iii) Dehydration of alcohol to ethers is catalysed by
Ans: (a) conc. H2SO4 at 413 K
(iv) The ether when treated with HI produces

Ans: Both a and d

Section – E 1*5=15

18. I An aromatic compound ‘A’ on treatment with CHCl3 and KOH gives two
compounds, both of which give same product ‘B’ when distilled with Zinc dust.
Oxidation of ‘B’ gives ‘C’ with molecular formula C7H6O2. Sodium salt of ‘C’ on
heating with soda lime gives ‘D’ which may also be obtained by distilling ‘A’ with
Zinc dust. Identify ‘A’, ‘B’, ‘C’ and ‘D’ giving sequence of reactions. (5)