CBSE Class 12 Chemistry 2016 Outside Delhi Set 1 Solved Paper

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Question : 26
Total: 26
(a) Write the structures of A and B in the following reactions :
(i) CH3‌COCl‌ ‌
H2,Pd−BaSO4
─────▸
‌A
‌
‌
H2N−OH
─────▸
‌B
.

(ii) CH3‌MgBr‌ ‌
1.CO2
─────▸
2â‹…H3O+
‌A
‌
‌
PCl5
─────▸
‌B
.
(b) Distinguish between :
(i) C6H5−COCH3 and C6H5−CHO,
(ii) CH3‌COOH and HCOOH.
(c) Arrange the following in the increasing order of their boiling points :
CH3‌CHO,CH3‌COOH,CH3CH2‌OH.
OR
(a) Write the chemical reaction involved in WolffKishner reduction.
(b) Arrange the following in the increasing order of their reactivity towards nucleophilic addition reaction :
C6H5COCH3,CH3−CHO,CH3COCH3
(c) Why carboxylic acid does not give reactions of carbonyl group ?
(d) Write the product in the following reaction.
CH3CH2‌CH=CH−CH2‌CN
‌ 1. ‌(i−Bu)2‌AlH
───────▸
‌ 2. ‌H2O
‌ ?
‌

(e) A and B are two functional isomers of compound C3H6O. On heating with NaOH and I2 isomer B forms yellow precipitate of iodoform whereas isomer A does not form any precipitate. Write the formulae of A and B.
Solution:  
(a) (i) CH3‌COCI‌ ‌
H2,Pd−BaSO4
─────▸
CH3‌CHO
[A] ‌Acetaldehyde
H2N−OH
─────▸
CH3−CH=N−OH
[B] ‌Acetaldoxime

(ii) CH3‌MgBr‌ ‌
1.CO2
─────▸
2â‹…H3O+
‌CH3‌COOH
PCl5
─────▸
CH3
‌COCI
+HCl
+POCl3

(b) (i) C6H5‌CHO being an aldehyde reduces Tollens' reagent to shining silver mirror whereas C6H5COCH3 being a ketone does not.
(ii) HCOOH gives silver mirror test with Tollens' reagent whereas ethanoic acid does not.
‌HCOOH+2[Ag(NH3)2]++2OH− →2‌Ag↓+2H2O+CO2+4NH3
‌CH3‌COOH‌ ‌
Tollens
─────▸
‌ reagent ‌
‌ No silver mirror
‌

OR(a)
(b) C6H5COCH3<CH3−COCH3 <CH3−CHO
(c) Carboxylicacids do not give reactions of carbonyl groups as it enters into resonance with lone pair of - COOH groups thereby making the carbon atoms less electrophilic.
(d)
CH3CH2‌CH=CH
Hex−3−enenitrile
−CH2‌CN
‌ 1. ‌(i−Bu)2‌AlH
───────▸
‌ 2. ‌H2O
CH3
CH2
‌CH
=CH−
CH2−
O
∥
C
−H
Hex−3−enal

(e)
CH3CH2‌CHO
Propanal‌ [A]
+NaOH
+I2
→
No yellow precipitate
CH3−
O
∥
C
−CH3
Acetone‌ [B]
+3‌NaOH
+4I2
∆
───▸
CHI3+3‌NaI
Iodoform(Yellow‌precipitate)
+CH3‌COONa
+3H2O
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