1.

Which of the following is formed as a result of biological oxidation of benzene in the body of the dog (a) Acrylic acid (b) Cinnamic acid (c) Maleic acid (d) Gluconic acid When acetylene is reacted with HBr, we get (a) Methyl bromide (b) Ethyl bromide (c) Ethylene bromide (d) Ethylidene bromide The only o, p-directing group which is deactivating in nature is (a) NH 2 (b)

2.

3.

OH

4.

5.

(c) (d) X (halogens) R (alkyl groups) Which kind of isomerism will butene-2 show (a) Geometrical (b) Optical (c) Position (d) None of these In presence of light toluene on reaction with chlorine gives (a) Benzoyl chloride (b) Ortho chlorotoluene (c) Para chloro toluene (d) Benzyl chloride If ethylene, carbon monoxide and water is heated at high temperature, which of the following is formed (a) C 4 H 8O2 (c) CH 3COOH (b) C 2 H 5COOH (d) CH 2 = CH COOH

6.

7.

Compound C 6 H 12 is an (a) Aliphatic saturated compound (b) Alicyclic compound (c) Aromatic compound (d) Heterocyclic compound Identify Z in the following series
HBr Hydrolysis 3 CH 2 = CH 2 X Y 2 Z I 2 excess Na CO

8.

(a) C 2 H 5 I (c) CHI 3 9.

(b) C 2 H 5 OH (d) CH 3 CHO

n-pentane and iso pentane can be distinguished by (a) Br 2 (c) conc. H 2SO4 (b) O3 (d) KMnO4

10.

11.

12.

CH CH + HBr X, product X is (a) Ethylene bromide (b) Vinyl bromide (c) Bromo ethane (d) Ethyledine bromide Assertion : 2-Bromobutane on reaction with sodium ethoxide in ethanol gives 1-butene as a major product. Reason : 1-Butene is more stable than 2-butene. Assertion : Styrene on reaction with HBr gives 2-bromo-2- phenyl-ethane. Reason : Benzyl radical is more stable than alkyl radical.

Answers and solutions

1. 2. 3.

(b) (d)

Biological oxidation of benzene gives cinnamic acid.

CH CH CH 2 = CH Br
HBr HBr

CH 3CH

Br Br

Ethylidene dibromide

(c) Electron accepting groups which make the substitution difficult are known or deactivating groups. o. p. directing groups are as follow :

CH 3, C2H 5(R),NH 2,OH , halogens (Cl, Br, I ) .

4. (a) 2-butene shows geometrical isomerism.

H C CH 3 ||
cis - Butene -2

H C CH 3 ||
trans - Butene -2

H C CH 3 CH 3 C H
5.

(d) Sidechain chlorination and temperature, light and in absence of halogen carrier. CH3 2
toluene
Cl

bromination

is

favoured

by

high

CH2Cl 2
Benzylchloride
Cl

CH2Cl
2
Benzalchloride
Cl

CCl3

Benzochloride

6. 7.

(b) (b)

Ligh temp. C2H 4 + CO + H 2O C2H 5 COOH Ethylene Propionic acid

Cyclohexane C 6 H 12 is alicyclic compound.

8.

(c)

CH 2 = CH 2 CH 3 CH 2
|

HBr

2 3 CH CH CHI 3 3 2
Hydrolysis

Na CO

Br

OH
1 alcohol

I2 excess Yellowppt ( Iodoform)

9.

(d)

On oxidation, with KMnO4 , they give different alcohols

KMnO4 CH 3CH 2CH 2CH 2CH 3 CH 3CH 2CH 2CH 2CHOH 2 n pentane [O]

OH | CH 3CH 2 C H CH 3 CH CH C C H | [O] 3 2 3 | CH 3 CH 3
KMnO4
3 alcohol

10. (b)

CH CH + HBr CH 2 = CHBr
Acetylene Vinyl brom ide

11. (d) 2-bromobutane on reaction with sodium ethoxide in ethanol gives 2-butene as a major product.

EtO
H C H CH (CH 3 ) Br EtOH + C H = CH + Br | | CH 3 CH 3
This is according to saytzeffs rule i.e. the Predominant product is the most substituted alkene, i.e. are carrying the largest number of alkyl substituents of hydrogen is eliminated preferentially from the carbon atom joined to the least number of hydrogen atoms. 2-butene is more stable than 1-butene due to presence of large number of hyperconjugating structures in 2-butene. 12. (b)

HBr adds to the double bond of the styrene forming 1-bromo-1-phenylethane.

Br

HBr

Styren e example of elimination-addition reaction. This is an Note : Here given assertion is wrong.