General Organic Chemistry 1079

1. The most stable conformation of n-butane is 11. How many primary amines are possible for the
[CBSE PMT 1997] formula C 4 H 11 N [MNR 1995]
(a) Skew boat (b) Eclipsed (a) 1 (b) 2
(c) Gauche (d) Staggered (c) 3 (d) 4
2. Which of the following undergoes nucleophilic 12. On monochlorination of 2-methyl butane, the total
1
substitution by SN mechanism [CBSE PMT 2005] number of chiral compounds is[IIT-JEE Screening 2004]
(a) Benzyl chloride (b) Ethyl chloride (a) 2 (b) 4
(c) Chlorobenzene (d) Isopropyl chloride (c) 6 (d) 8
3. Which type of isomerism is shown by propanal 13. An isomer of ethanol is
and propanone [CPMT 2004] [DPMT 1982, 88; CPMT 1973, 75, 78, 84; IIT-JEE 1986;
BHU 1984, 85; EAMCET 1993; MP PET 1995;
(a) Functional group (b) Metamerism
RPET 1999; BHU 2000; AFMC 2002]
(c) Tautomerism (d) Chain isomerism
(a) Methanol (b) Dimethyl ether
4. Which of the following exhibits optical isomerism
(c) Diethyl ether (d) Ethylene glycol
[BHU 1980; NCERT 1983; AIIMS 1992;
14. Due to the presence of an unpaired electron, free
MNR 1993; MP PMT 1990, 94]
radicals are [
(a) Butanol-1 (b) Butanol-2
(a) Chemically reactive (b) Chemically inactive
(c) Butene-1 (d) Butene-2 (c) Anions (d) Cations
5. In carbonium ion the carbon bearing the positive 15. Tertiary alkyl halides are practically inert to
charge in the [Pb. PMT 1999; MH CET 2002] substitution by S N 2 mechanism because of [AIEEE 2005]
(a) sp 2 -hybridized state (b) sp 3 d -hybridized
(a) Insolubility (b) Instability
state
(c) Inductive effect (d) Steric hindrance
(c) sp -hybridized state (d) sp 3 -hybridized state 16. The decreasing order of nucleophilicity among the
6. Which of the following is not an electrophile nucleophiles
[CBSE PMT 2001] (i) CH 3 C  O  (ii) CH 3 O 
||
 
(a) Cl (b) Na O

(c) H (d) BF3 (iii) CN  (iv)
7. Heterolytic bond dissociation energy of alkyl O
||
halides follows the sequence [AMU 2000] H 3C   S  O
(a) R  F  R  Cl  R  Br  R  I ||
O
(b) R  I  R  Br  R  Cl  R  F
is [AIEEE 2005]
(c) R  I  R  F  R  Br  R  Cl
(a) (i), (ii), (iii), (iv) (b) (iv), (iii), (ii), (i)
(d) R  Cl  R  Br  R  I  R  F
8. The shape of carbonium is [AMU (Engg.) 1999] (c) (ii), (iii), (i), (iv) (d) (iii), (ii), (i), (iv)
(a) Planar (b) Pyramidal 17. Which of the following is optically active [BHU 2005]
(c) Linear (d) None of these (a) Butane (b) 4-methylheptane
9. Which of the following compounds shows (c) 3-methylheptane (d) 2-methylheptane
tautomerism 18. Correct configuration of the following is
[MP PET 2001] CH 3
(a) HCHO (b) CH 3 CHO H OH
[AIIMS 2005]
(c) CH 3 COCH 3 (d) HCOOH CH 3 OH
10. In which bond angle is the highest [CBSE PMT 1991] H
(a) sp 3 (b) sp 2 (a) 1S, 2S (b) 1S, 2R
(c) sp 3
(d) sp d (c) 1R, 2S (d) 1R, 2R
19. Which types of isomerism is shown by 2, 3-
dichlorobutane
 1080 General Organic Chemistry
[AIEEE 2005] (a) Kolbe (b) Wohler
(a) Distereo (b) Optical (c) Fraizer (d) Berzilius
(c) Geometric (d) Structural
20. Who synthesised the first organic compound urea
in the laboratory [RPMT 2000]

(SET -23)

CH 3  CH 2  CH  CH 3
CH3 |
NH 2
H H
1. (d) Anti or completely staggard (2- aminobutan e)

CH 3
H H |

CH3 CH 3  C  CH 3
|
NH 2
Staggard form is most stable because of (2- Methy l- 2 - am inopropa ne)
minimum repulsion between bulky methyl
groups.
3 2
CH 3  CH  CH 2  NH 2
1
***
|
2. (a) Due to more stable carbocation.
CH 3
3. (a) When two compounds have similar molecular (2- Methy l-1 - am inopropa ne)
formula but differ in the functional group then 12. (b) The possible monochlorinated products of 2-
the isomerism is called functional group methyl butane are
O Cl
||
isomerism i.e. CH 3CH 2CHO and CH 3 . C CH 3 . *
Cl
H (+) and (–)
|

forms
4. (b) CH 3  C  CH 2  CH 3
|
OH
Cl *
Because it has chiral carbon atom.
Cl
5. (a) The central carbon atom in carbonium ion is (+) and (–)
sp 2 hybridised and it has three sp 2 hybrid forms
Therefore, a total of four chiral compounds
orbitals for single bonding to three are obtained.
substituents.
13. (b) Dimethyl ether is an isomer of ethanol.
6. (b) Na  is not an electrophile. 14. (a) Free radicals are very reactive due to the
7. (b) R  I  R  Br  R  Cl  R  F presence of free e–.
8. (a) Carbonium ion is planar species 15. (d) Due to steric hinderance
9. (c) Ketones show tautomerism. They form keto 16. (c) (ii) > (iii) > (i) > (iv)
and enol form CH 3
|
O OH 17. (c) CH 3 CH 2*CHCH 2 CH 2 CH 3 has a chiral carbon
|| |
Tautomerism
CH 3  C  CH 3 CH 3  C  CH 2 atom and hence is optically active.
10. (c) Type Bond angle 18. (a) CH3
3 o
sp 109 . 5
2 H O
sp 120 o
H
sp 3 d 90 o and 120 o
CH3 O
sp 180 o H
11. (d) CH 3  CH 2  CH 2  CH 2  NH 2 H
(1- aminobutan e)
 General Organic Chemistry 1081
Following the procedure outlined under
'Golden Rule' the absolute configuration is 1s,
2s.

CH 3 CH 3
19. (b) H Cl , H Cl ,
H Cl Cl H
CH 3 CH 3

CH 3
Cl H
H Cl
CH 3
20. (b) Wohler synthesised the first organic
compound urea in the laboratory.