CHAPTER 15- GENERAL ORGANIC CHEMISTRY

Single Correct Type

1. The correct order of increasing C – O bond length in CO,
CO 32 – , CO2 is –

(A) CO 32– < CO2 < CO (B) CO2 < CO 32– < CO
(C) CO < CO 32– < CO2 (D) CO < CO2 < CO 32–

O
||
2. When is reacted with mesitylene in the presence of
F3C–C–O–OH

BF3, the product formed is -

Me
Me

(A) (B)
Me Me
Me Me
BF3
O–CH–CF3

O–H
Me Me

(C) (D)
Me Me Me Me
OH C–CF3
O

1
3. Identify the product when cyclopentanone undergoes
reaction with D2O and KOD.
O O
D

(A) (B) D

D D O
D
O D
(C) (D)
D
D

4. A conversion of 2,5-dimethylfuran into 2,5-dimethylpyrrole

may be accomplished in two steps:
I. Hydrolysis of the furan in aqueous acid.
II. Heating the hydrolysis product with excess ammonium
carbonate
What is the intermediate hydrolysis product used in the
second step ?

O N
H

(A) 2,5-hexanedione
(B) 3,4-hexanedione
(C) hexanedial
(D)2,5-dimethyl cyclopentanone

2
5. The product of the given reaction is

Na
CH 3OH , 

(A) (B)
(C) (D)

6. The correct order of pKa of following substance in aqueous

solution is
H

O N O NH2
+ +
+ N H NH3
NH2 NH2
(i) H
(ii) (iii) (iv)

(A) (i) > (ii) > (iii) > (iv) (B) (iv) > (iii) > (ii) > (i)
(C) (ii) > (iii) > (iv) > (i) (D) (i) > (iii) > (ii) > (iv)

7. The molecule which has the shortest carbon-oxygen bond

length is -
(A) CH –CH–CH
3 2 (B) CH – CH 2 2

O O
CH2

(C) CH3–O–CH = CH2 (D) CH3 – CH2OH

3
 H OTs

H
8. PhCO2 OMe
NaI

DMSO
H OMe
H

Major product which you expect in the above reaction is -

H H
OTs I
H H
(A) I OMe
(B) PhCO2
OMe
H OMe H OMe
H H
I H
H OTs
H I
(C) PhCO2
OMe
(D) PhCO2
H
H OMe H OMe
H H

9. Where does cross conjugation occurs?

(I) C6H5 CH2CONH2 (II) C6H5CONH2
(III) Quinone (IV) C6H5OCOCH = CH2
(A) I, II and III (B) I, II and IV
(C) II, III and IV (D) I, III and IV

10. Consider the following compounds:

NH2 NH2 NH2 NH2

NO2 CN CH3

(1) (2) (3) (4)

Arrange these compounds in decreasing order of their

basicity -
4
 (A) 1 > 2 > 3 > 4 (B) 2 > 3 > 1 > 4
(C) 4 > 1 > 3 > 2 (D) 4 > 1 > 2 > 3

Multiple Correct Type

11. Which of the following species is/are aromatic
(A) (B)

SbCl6
Ph

(C) (D) 
 H
Ph

12. Choose the correct reaction as per the given major product
(s)
H3CO
14 H 14
I KNH2
(A) C C
Br
H3C O C C Cl
Cl
(Major)

H3C O
14 H 14
II KNH2
(B) C C H3CO C C Cl
Cl Br
(Major)

5
 Cl + OH
14 H
III
(C) C N C N Cl
14
OH

O
+
H3O
(D)
IV Cl C O OH Cl C + HO CH3

CH3

13. In which of the following cases the first compound has

higher dipole moment than the second?
(A) CH2 = CH—Cl & CH3—CH2—Cl
NO2

(B) & H3C NO2

Ph

(C) O & O

Ph

(D) CH3—CH=CH—CHO and CH3CH2CH2CHO

14. The rearrangements in which the alkyl isocyanate (RNCO)

is formed as an intermediate is are
(A) Hoffmann-bromamide reaction
(B) Schmidt reaction
(C) Curtius reaction
(D) Lossen reaction
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15. Select the correct option against mentioned property

(A)

(B)
(Rate of reaction with CH 3 I ) (Basic nature)

(C)
(D) I  F (Nucleophilicity)
 

Rate of reaction with H SO 2 4

16. Stability of alkyl carbocation can be explained by

(A) Inductive effect (B) Hyperconjugation
(C) Electromeric effect (D) None of these

17. The correct order of Acidity is

(A) CH  CH  CH  CH
3 3 (B) CH3OH  H 2O

(C) H2O < OH (D) OH < CH3COOH

7
18. The species not observed in the following sequence of
reaction –
O
* Cl
*

RO–

O RO O–
* Cl
* **

(I) RO– (VI)

O RO
* O
* OR * RO O
*
**

(II) (IV)
+ + (VII)
H RO
OR
** O *
O
*

(III) (V)

(A) I, II, III (B) II, III, VII

(C) VI, VII (D) I, IV, V

19. Select the correct statement (S):

(A) when carbocations are intermediate substantial secondary
isotope effects are observed.
(B) In case of an organic reaction showing primary isotope
effect, the zero point energy of C–D bond lies lower than
C–H bond.
(C) An inverse isotope effect is observed if coordination at
the reaction centre increases in the transition state.
(D) The reaction
8
 H*
|
CH3O C = O + HCN
H*
|
 CH3O C H
|
CN

is an example of secondary kinetic isotope effect.

20. Select the correct order among the following:

(A) Order of heat of hydrogenation < <

(B) Order of heat of combustion > >

(C) Order of resonance energy < <

NH NH NH

HN NH NH
(D) Order of basic strength > >

Integer Type
21. How many compounds are electrophiles?
CO2 ,SnCl2 , FeCl3 , NH4 , BF3

22. Out of following how many are electrophiles?

+ + –
NO2, NH4, :CCl2, AlCl3, :CCl3, SO3

23. How many hyper conjugative structures are possible in


(CH3 )2 C H

24. How many hyper conjugative structures are shown in

following alkene
9
 CH3
H3 C C CH CH2
CH3

25. How many among the following are stronger acid than
CH3COOH?
CH3

CH3CH2COOH, CH  CH 2 COOH , HCOOH

CH3

ClCH2COOH, CH3CH2OH
26. Total number of hyperconjugation structure possible for
(CH3)2CH+ is
27. How many hyperconjugated structures are possible for the
free radical (CH3)2 C H ?
28. The number of hyper conjugative structure for the given
compound
CH3 CH3
CH3
C=C
H C=C
H H will be?
29. What is the total number of resonating structures that are
possible for the given compound
CH3 Br

CH 2CH 3

30. Total number of electrons with carbons in carbene is

10
 SOLUTIONS
Single Correct Type
1. (D)
C O has lowest bond length due to highest bond order.
O = C = O has second lowest bond length due to doubled
bond.
O

C
has highest bond length due to lowest bond order
O O

which is due to resonance.

2. (C)
Me H H
Me
F3C–C–O–OH+BF3 F3C–C–O–OH + +
O O–BF3
Me

OH
O
Me 
Me F3C–C–OBF3 H OH
CF3COOH + BF3 + Me Me
+

Me
Me

3. (C)
H

O OH O–D
D2O

All -hydrogen atoms are replaced by D due to tautomerism.

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4. (A)
H+,H2O
O Heat O O OH
+

NH4+
N OO
NH2 O
H

5. (C)
Since Naphthalene is less aromatic in character than benzene
therefore its double bonds are reduced to give tetralin.

6. (C)
* Presence of two EWG and resonance stablisation makes
(i) strongest acid
* In (ii), two NH2 group acts as ERG through resonance after
the loss of H+ therefore loss of H+ is most difficult.

7. (C)
.. 
CH3–O–CH
.. = CH2 CH3–O=CH
.. – CH
.. 2


Here C–O bond acquires double bond character hence C–O

bond length is minimum among the above compound.

8. (C)
–
S N reaction takes place in which I will act as
2

nucleophiles and ¯O Ts will act as leaving group.

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9. (C)
..
.. O:
O:
||
|| . .
C– NH2 ..
O:
|| . . ||
. . – C–CH=CH2
O
. .:
O

(II) (III)
(IV)

10. (C)
0   + –
NH2 NH2 NH2 NH2

NO2 CN CH3
–M –M +H
(1) (2) (3) (4)

Multiple Correct Type

11. (A, B, C)
For a compound to be aromatic, there must be cyclic
delocalization with the closed loop formed must have (4n +
2)  electrons. In the given case, (a), (b) and (c) qualify to be
called as aromatic.

12. (A, C)
(A)

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 (C)

13. (B, D)
H
H
H3C CH 2 C C O H3C CH 2 C C O
H H H
H
smaller charge reparation
H H
H3C C CH CH C CH3 H3C C CH CH C O

H O H H
larger charge separation - leads to higher dipole moment

14. (A, B, C, D)
In all RNCO is intermediate. Refer the mechanism.

15. (A, B, D)
Due to bridge structure the l.p will not flip I is a good 

leaving group than F 

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16. (A, B)
By inductive effect and hyper conjugation carbocation are
stabilished.

17. (A, B, C, D)
Order of Acidity is

OH < CH3COOH
CH3  CH3  CH  CH  CH3OH  H 2O  H 2O 

18. (B, C)

The path of the reaction is.

RO O OR
O O
* *
* * Cl * * RO– *
*
+

19. (A, B, C, D)
The change in rate of reactions by isotopic substitutions.
When substituted H-atom (isotope) is don’t directly involved
in the reaction is known as secondary isotope effect. When
RH
RD
> 1 normal secondary isotope effect.

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 RH
RD
< 1 inverse secondary isotope effect.

20. (B, C, D)

(A) < <

HOH  1
stability

1 H 3 H 4 H

correct order < <

(B) < <

HOC  No. of cation

(C) < <

Resonance energy  delocalisation/conjugation simple <

cross < exterded
NH NH NH

(D) HN NH > NH >

Basicity  e– density on N atom

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 Integer Type
21 (4)
Electrophiles = CO2 , SnCl2 , FeCl3 , BF3

22 (4)
+ + –
NO2, :CCl2, AlCl3, SO3 are electrophiles but not NH4, :CCl3

23. (6)
In carbocation 6  hydrogen atom are present so
hyperconjugative structure will be 6.

24. (0)
Here is no any  hydrogen so hyper conjugative structure
will be zero (0).

25. (2)
Stronger acids are HCOOH and ClCH2COOH.

26. (7)
No. of hypercanjugation structure = no. of H +1

27. (6)
Number of alpha hydrogen = Hyperconjugated structures

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28. (9)
CH 3 CH 3
C=C CH 3 9 α = hydrogen = 9 hypercongative
H C=C structure
H H

29. (6)
Each aromatic ring can have three resonating forms.

30 (6)
19. H — C:

H
Total numbers of electrons with C
=4+2=6

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