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?

(a) 2-methyl propene-2-ol (b) 2-methyl 1 -propanol
(c) Butane-2-ol (d) Butane 1-ol
2. One mole of ethyl acetate on treatment with an excess of LiAlH 4 in dry ether
and subsequent acidification produces
(a) 1 mole acetic acid + 1 mole ethyl alcohol
(b) 1 mole ethyl alcohol + 1 mole methyl alcohol
(c) 2 moles of ethyl alcohol
(d) 1 mole of 2-butanol
3. Which of the following reagents cannot, be used to oxidise primary alcohols
to aldehydes?
(a) CrO3 in anhydrous medium (b) KMnO4 in acidic medium
(c) Pyridinium chlorochromate (d) Heat in the presence of Cu at 573 K
4. 1-Phenylethanol can be prepared by the reaction of benzaldehyde with
(a) methyl bromide (b) ethyl iodide and magnesium
(c) methyl iodide and magnesium (d) methyl bromide and aluminium bromide
5. Which of the following alcohols will give the most stable carbocation during
dehydration?
(a) 2-methyl-1-propanol (b) 2-methyl-2-propanol
(c) 1-Butanol (d) 2-Butanol
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
(a) CH3CH2OCH3 (b) CH3CH2CHO
(c) CH3CH2CH2OH (d) CH3CHOHCH3
7. Order of esterification of alcohols are
(a) 3° > 1° > 2° (b) 2°> 3° > 1°
(c) 1 ° > 2° > 3° (d) None of these
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.
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.
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.
(b) Ortho-nitro phenol is more acidic than ortho-methoxyphenol.
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
15. Give reasons for the following :
(a) Phenol is more acidic than methanol.
(b) The C—O—H bond angle in alcohols is slightly less than the tetrahedral
angle (109°28′).
(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.
16. (a) Give a seperate chemical test to distinguish between the following pairs
of compounds:
(i) Ethanol and Phenol (ii) Methanol and Propan-2-ol.
(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:
(a) Methoxybenzene (b) Benzyl p-nitrophenyl ether
(c) tert. butyl methyl ether (d) Di tert. butyl ether
(ii) The I.U.P.A.C. name of the ether CH2 = CH-CH2O CH3 is
(a) Alkyl methyl ether (b) l-Methoxy-2-propene
(c) 3-Methoxy-l-propene (d) Vinyl dimethyl ether
(iii) Dehydration of alcohol to ethers is catalysed by
(a) conc. H2SO4 at 413 K (b) Hot NaOH
(c) Hot HBr (d) Hot HNO3
(iv) The ether when treated with HI produces

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)
(or)
II (a) An organic compound ‘A‘having molecular formula C3H6 on treatment with
aq. H2SO4 give ‘B’ which on treatment with Lucas reagent gives ‘C’. The
compound ‘C’on treatment with ethanolic KOH gives back ‘A’.Identify A,B,C . (3)
(b) Arrange the following compound groups in the increasing order of their
property indicated:
(i) p-nitrophenol, ethanol, phenol (acidic character)
(ii) Propanol, Propane, Propanal (boiling point) (2)