GOC & ISO, CARN

Multiple correct choice type

1. Which of the following compounds on dichlorination gives 3 different products (may not
occur by same mechanism in all compounds and even low yield products are to be counted).

(a) (b)

CH3

(c) (d)

1. AB

2. Which of the following pairs represents enantiomers?

NH2 H CH3 OH
H OH H3C H
(a) H3C H , HO2C CH3 (b)
H Cl , H CH3
CO2H NH2 CH3 Cl

CH3 H NH2 CH3

H OH H3C OH H CO2H CO2H H
(c) (d)
H Cl , H3C Cl H OH , HO H
CH3 H CH3 NH2
2. AC

5. Identify among the following, set of functional isomers.

(a) CH3CH2CH2CO2H & CH3CHCH3 (b) CH3CH2CO2H & CH3CO2CH3
CO2H
CH3
(c) CH3CH2CH2NH2 & CH3NCH3 (d) CH3CH2COCH2CH3 & CH3COCH
CH3 CH3

5. BC

6. Which of these are isomers for an aromatic compound having molecular formula C7H8O?
CH3 CH2OH
OH
(a) (b)

CH2OCH3 OCH3

(c) (d)

6. ABD

CH3
11. CH3CHCH2CH2CH3 on monochlorination with Cl2 in the presence of light at room
temperature (reaction proceeds by free radical mechanism) gives ‘p’ isomers. The product
mixture on fractional distillation gives ‘q’ fractions. Which of the following option is correct?
 (a) ‘p’ is 8 (b) ‘p’ is 7
(c) ‘q’ is 4 (d) ‘q’ is 5
11. AD

12. Which of the following compounds have anti conformer as the most stable conformer?
(a) CH3CH2CH2CH3 (Rotation about C2C3 bond)
(b) ClCH2CH2Br
(c) ClCH2CH2OH
(d) HOCH2CH2CH3
12. ABD

13. Which of the follower compounds/isomers have centre of symmetry?

NO2 Me3C
O
CO2Et
(a) (b)
EtO2C
CMe3 NO2 O
(trans isomer)

CH3
CH3
H3C H
H H OH
(c) H (d)
HO H
H CH3
CH3
CH3
13. BC
14. A mixture of racemic C2H5CHCO2H can be resolved by reacting with
CH3
(a) C2H5CHOH (b) C2H5CHNH2
CH3 CH3
(c) CH3CHNH2 (d) CH3CHOH
CH3 CH3
14. AB

15. Which of the following pair represents structural isomers?

H3C C2H5 H3C H
(a) C=C and C=C
H H H C2H5
(b) CH3COC2H5 and CH3CH2CH2COH
O O
(c) CH3CH2OCH2CH2CH3 and CH3OCHCH2CH3
CH3
(d) CH3CH2N=O and CH3CH=NOH
15. BCD

1. Identify the species which is not capable of acting as an electrophile.

(a) BCl3 (b) AlCl3

(c) NH 4 (d) CO2

2. Which of the following species is a nucleophile but not an electrophile?

  
(a) NH 4 (b) NH 3 OH
(c) H3O (d) CH3CCH3
O
3. Which is the most stable carbocation?

(a) (CH3)2CH+ (b) CH2

(c) CH2  CH  CH2 (d) (CH3)3C+

4. Steric inhibition of resonance can be expected in

(a) N (b) N

(c) N (d) N

5. Which free radical is the most stable one?



(a) CH2 (b) CH2

CH3
 
(c) (CH3)3C (d) (CH3)2CH

6. Which of the following represents the correct order of acidic strength?

(a) HCO2H > CO2HCO2H (b) CH3CO2H > HCO2H
(c) CO2HCO2H < CO2HCH2CO2H (d) CO2HCO2H > HCO2H

7. Which one of the following intermediate is electrically neutral?

(a) Carbanion (b) Benzyne
(c) Carbon free radical (d) both (b) and (c)

8. Which one of the following is an incorrect statement?

(a) Aniline shows stronger resonance than phenol.
(b) 2,6dimethyl4nitrophenol is more acidic than 3,5dimethyl4nitrophenol.
. .
(c) CH2CH=CHCH2 is a valid resonance structure of CH2=CHCH=CH2.
(d) Benzyl free radical is more stable than tbutyl free radical.

9. In which of the following molecule, the group attached to benzene does not show any type of
resonance effect?

(a) NH2 (b) NH3

(c) OH (d) Cl
10. Which of the following is correct order regarding the acidic strength of carboxylic group?
(a) CH3CH2CH(Cl)COOH > CH3CH(Cl)CH2COOH > ClCH2CH2CH2COOH
(b) CH3CH2CH(Cl)COOH < CH3CH(Cl)CH2COOH < ClCH2CH2CH2COOH
(c) CH3CH2CH(Cl)COOH > CH3CH(Cl)CH2COOH < ClCH2CH2CH2COOH

(d) CH3CH2CH(Cl)COOH < CH3CH(Cl)CH2COOH > ClCH2CH2CH2COOH

11. Which of the following is correct order regarding I effect of the substituents?
(a) NH2 > OH > F (b) NH2 < OH < F
(c) NH2 > OH < F (d) NH2 < OH > F
12. Which of the following order is not the correct order regarding I effect of the substituents?

(a) I < Cl < Br < F (b) NR2 <  O R 2

(c) NR2 < OR < F (d) SR < OR <  OR 2
13. Which of the following is correct order regarding the acidic strength of carboxylic acids?
(a) (CH3)3CCOOH > (CH3)2CHCOOH > CH3CH2COOH
(b) (CH3)3CCOOH > (CH3)2CHCOOH < CH3CH2COOH
(c) (CH3)3CCOOH < (CH3)2CHCOOH > CH3CH2COOH
(d) (CH3)3CCOOH < (CH3)2CHCOOH < CH3CH2COOH

14. Which of the following compound has the highest pKa value?
OH OH
Cl NO2
(a) (b)

OH OH
CH3 OCH3
(c) (d)

15. Which is the most stable singlet carbene among the following?
.. ..
(a) CF2 (b) CCl2
.. ..
(c) CBr2 (d) CI2

16. Which of the following nitrogenous base is the strongest in water?

(a) (b)
N N
H H

(c) (d)
N N
H
17. In which one of the following compounds delocalisation is not possible?
(a) 2butene (b) 1,3butadiene
(c) 1,3,5hexatriene (d) Benzene
18. Consider the following carbocations:
 
(1) CH3CH2 (2) CH2=CH
 
(3) CH2=CHCH2 (4) C6H5CH2
Stability of these carbocations in decreasing order is
(a) (4) > (3) > (1) > (2) (b) (4) > (3) > (2) > (1)
(c) (3) > (4) > (2) > (1) (d) (3) > (4) > (1) > (2)

19. Which one of the following cation is most acidic?

   
NH3 NH3 NH3 NH3

(a) (b) (c) (d)

OH NO2 CH3

20. Decreasing order of stability of given carbocations is



(1) (2) CH2=CHCH2
 
(3) C6H5CH2 (4) CH3CHCH3
(a) (3) > (2) > (4) > (1) (b) (1) > (3) > (4) > (2)
(c) (1) > (3) > (2) > (4) (d) (3) > (2) > (1) > (4)

ONE OR MORE THAN ONE CHOICE CORRECT

1. The correct order of the stability of the given resonating structures is

 
CH2CHCH=CHOCH3 CH2CH=CHCH=OCH3
(I) (II)
 
CH2=CHCHCHOCH3 CH2=CHCHCH=OCH3
(III) (IV)
(a) (IV) > (II) > (I) > (III) (b) (IV) < (II) < (III) < (I)
(c) (III) < (I) < (II) < (IV) (d) (I) > (III) > (II) > (IV)

2. Which of the following substituent shows +R effect on benzene ring?

O
NHCCH3 OCH3 C(CH3)3 O

(a) (b) (c) (d)

 (a) (b)
HO2C CO2H
3. The correct acidic strength order of the indicated groups in the given

NH3
(c)
compound is
(a) (b) > (a) > (c) (b) (a) < (b) < (c)
(c) (c) > (b) > (a) (d) (c) < (a) < (b)

4. Which of the following is true about carbenes?

(a) Carbenes can be formed by elimination of CHCl3.
(b) Carbenes can do nucleophilic attack.
(c) Among alkylated carbenes, singlet form is more stable than triplet form.
(d) Carbenes can undergo addition to double bond to give cyclopropyl systems.

5. In which of the following molecules all the effects namely inductive, mesomeric and
hyperconjugation operate:

(a) Cl (b) COCH3

CH3

(c) CH3 (d) CH3CH=CHCl

CH3

6. is more basic than because

..
N
.. N
H

(a) is a six membered aromatic ring.

N
..

(b) Lone pair of is not taking part in delocalization.

N
..

(c) Lone pair of is taking part in delocalization.

..
N
H

(d) is an aromatic amine.

..
N
H

7. Which of the following compound/species is/are aromatic species?

O
(a) (b)
 
O

(c) (d)

8. Which of the following represent(s) correct order of acidity?

(a) CHF3 > CHCl3 (b) CHCl3 > CHF3

(c) > (d) >

O O S S S S O O

9. Which of the following intermediate is aromatic in nature?

CH3

 :
(a) (b) (c) (d) (singlet)
..

10. In which of the following pairs, first member is more stable than the second?
  .
(a) (C 6H5 ) 3 C , (C 6 H5 ) 2 C CH3 (b) :CH2, CH2
.
 

(c) (C6H5)3C: , :CH3 (d) (C 2H5 ) 3 C, (CH3 ) 3 C

1. (a, c) 2. (a, b, d) 3. (a, d) 4. (a, d) 5. (b, d)

6. (b, c) 7. (a, b, c) 8. (b, d) 9. (a, b) 10. (a, c)

(MULTIPLE ANSWER TYPE)

1.

Ans: ABD
2.

Ans: ACD
3.

Ans: BCD
4.

Ans: ABD
5.

Ans: BCD
6.

Ans: ABC
7.

Ans: CD
8.

Ans : AC
Sol : AC

9.
 Ans : ABD
Sol :

Numerical type

1. The maximum number of structural isomers (alkene) with the molecular formula C4H8 is
1. 3

2. The number of optically active isomers of C3H5Br3 is

2. 2

3. Total number of optical isomers of COOH(CHOH)2COOH is

3. 3

4. For the compound, total number of optical isomers will be

4. 4

5. Total number of isomeric alcohols with the molecular formula C4H10O is

5. 4

6. nHeptane on monochlorination gives a number of isomers. How many of them are optically
active?
6. 2

7. Which nitrogen in Lysergic acid diethylamide (LSD) is most basic?

(1) O
(3)
HN
(2) CN(C2H5)2
N
CH3
7. 2

1.

Ans: 4
2.

Ans:6
Sol:

3.

Ans:3
Sol:

4.

Ans:2
Sol:

5.
 Ans:6
Sol:

Decimal type

1. (+) Mandelic acid has a specific rotation of +158°. What would be the observed specific
rotation of the mixture of 25% () mandelic acid and 75% (+) mandelic acid?
7. +79o