JEE (Mains) GOC & Isomerism

The correct order of stabilities of the following resonance structures is :

1. 4

a)
b)
c)
d)
Ans: 2
i. The lesser the charge separation, the more stable the resonating structure. (I) and (III) have less charge separa
tion. But in (III),+ve charge is on electronegative N atom. Therefore, (I) is more stable than (III).
ii. (II) is more stable than (IV) because in (II) positive charge is on electropositive C atom and negative charge
Exp:
is on EN (electronegative) N atom, whereas in (IV) it is reversed.
Therefore, .
So, the stability order is :

An organic molecules has 5 bonds (heat of hydrogenation for bond is 28.8 kJ mol-1) and expe
2. 4
rimental value for heat of hydrogenation is 99 kJ mol-1. The resonance energy in kJ mol-1 is
a) 45
b) 90
c) 70
d) 140
Ans: 1

Exp:

Resonance energy = ( Hydrogenation) = Theoretical - Experimental

3. AlCl3, SO3, PCl3 are 4

a) Neutral nucleophile
b) Neutral electrophile
c) Cationic electrophile
d) Anionic nucleophile
Ans: 2
4. 4

Given compound is
a) 2 - Bromo - 3 - nitrobutanal
b) 1- Bromo -1 - formy 1 -2 - nitropropane
c) 3 - Nitro - 2 - bromobutanal
d) All are correct
Ans: 1

5. Which of the following has incorrect name corresponding to alkoxy group? 4

a)

b)

c)

d)

Ans: 4
6. 4

IUPAC name of the given compound is

a) 2 - carboxy - 4 - iodocyclopentanol
b) 4 - lodo - 2 - hydroxycyclopentane acid
c) 2-hydoroxy-4-lodo-cyclopentanecarboxylic acid
d) 3 - lodo - 5 - hydroxy cyclopentane carboxylic acid
Ans: 3

The decreasing order of +I effect of the following is:

7. 4
I. - II. Me- III. Et- IV. Me2CH- V. Me3C-
a)
b)
c)
d)
Ans: 3
Exp: Factual

Place the following in the correct order of acidity.

8. 4

a)
b)
c)
d)
Ans: 1
As more stable is carboxylate ion, more is acidic strength.

Exp:

s character E.N of carbon stability of anion.

 Order of stability of given carbocations is :

(I) (II) (III)

9. 4

a) I > II > III

b) III > I > II
c) II > III > I
d) II > I > III
Ans: 2

10. In which of the following molecules, all atoms are not coplanar? 4

a)

b)
c)

d)

Ans: 3

Exp:

Due to this sp3 hybridized C atom all the atoms in this molecule are not coplanar.

11. Which of the following is true about resonance? 4

a) Due to resonance only bond order changes
b) Due to resonance only bond length changes
c) Due to resonance both bond order and bond length changes
d) None of these above
Ans: 3
By resonance single bond is converted into double bond and vice versa, hence bond order changes as a result b
ond length also changes.

Exp:
 Which of the following is true for compound (X)?

12. 4

a) Lone pair on nitrogen (A) will participate in resonance

b) Lone pair on nitrogen (B) will participate in resonance
c) Both lone pair on nitrogen (A) and (B) will participate in resonance
d) None of the lone pair will participate in resonance.
Ans: 2

Exp:

13. In which of the following compounds lone pair on nitrogen does not participate in resonance 4

a)

b)

c)

d) All the above

Ans: 2

Exp:

Here lone pair in N-is not in congested with the p orbital of benzene ring

14. Which of the following compound does not exhibit resonance? 4

a)

b)

c)

d) All the above

Ans: 3

Exp:
This molecule does not have more than two congested & coplanar P orbital.

15. Which of the following is not true ? 4

a) is stable due to resonance

b) is unstable due to inductive effect

c) is stable due to resonance

d) is stable due to inductive effect

Ans: 3

Exp: is stable by hyperconjugation and inductive effect not by resonance

16. Which of the following is electron deficient species___ 4

a)

b)

c)

d) both a' and b'

Ans: 4

Exp:

Both carbocation and free radical are electron deficient species.

17. Which of the following exhibits +M effect? 4

a) -NO2
b) -NH2
c) -CN

d)

Ans: 2
-NO2, -CN, and -CHO has M effect
Exp:
-NH2 exhibits +M effect.

18. The most unlikely representation of resonance structure of p-nitro phenoxide ion is 4

a)

b)
c)

d)

Ans: 3

Exp:

Is the most unlikely resonating structure because here N. is pentavalent.

19. Which of the following alkenes will show maximum number of hyper conjugation forms? 4

a)

b)

c)
d)

Ans: 1
More is the number, of , more is hyper conjugative structure.

Exp:

20. Which of the following is strongest acid? 4

a)

b)
c)

d)

Ans: 2

Exp:

Due to I and R effect of NO2 C.B gets stabilization, Therefore option B, is the correct answer

Which of the following group destabilizes the carbocation X'?

21. 4

a) CH3
b) OCH3
 c) NO2
d) Both 1' and 2'
Ans: 3
(X) is a carbocation any group which has electron donating nature stabilizes (X) and any group which has elect
Exp: ron withdrawing nature destabilized (X).
As NO2 has (-)I and R effect, It destabilizes (X).

22. 4

Molecules (x) is-

a) anti-aromatic
b) aromatic
c) non-aromatic
d) None of these
Ans: 2

Exp:

6 electron, planar, conjugate aromatic.

23. 4

Which of the following is / are correct statements?

a) (I) is more basic them (II)
b) (II) is more basic them (I) and (III)
c) (III) is more basic them (II)
d) None of these are correct
Ans: 2
More is the availability of l.p. on n more basic the compound is.

l.p. on N participates in resonance to give the compound more stabilit

y so, l.p. is least available here.

Exp:
l.p. on N- is in conjugation with the ring electron , therefore l.p. is al

so less available here but availability here is more than the previous case.

l.p. here does not participate in resonance, therefore availability is high an

d most basic than others.

Write the order of strength of the following substituted benzoic acid?

24. 4

a) II III I IV
b) I II IV III
c) IV III II I
d) III II I IV
Ans: 1
Exp: Is most acidic due to Ortho effect steric inhibition of resonance of the COOH is near.

25. An isomer of ethanol is : 4

a) Methanol
b) Diethyl ether
c) Acetone
d) Dimethyl ether
Ans: 4
Exp: Ethanol is a functional isomer of dimethyl ether, as both have the same molecular formula.
26. 4

Which of the following is true__

a) (I) and (II) are metamers
b) (II), (III) and (IV) are chain isomers
c) (II) and (IV) are not - metamers
d) All the above
Ans: 4
Exp: Definition

27. Which of the following compounds will exhibit geometrical isomerism? 4

a) 1-Phenyl-2-butene
b) 3-Phenyl-1-butene
c) 2-Phenyl-1-butene
d) 1,1-Diphenyl-1-propene
Ans: 1
Compounds of the type

Exp:
 IUPAC name of

28. 4

a) 5-Chloro-(2E, 4E)-hexa-2, 4-diene

b) 2-chloro-(2E, 4E)-hexa-2, 4-diene
c) 2-chloro-(2E, 4Z)-hexa-2, 4-diene
d) 2-chloro-(2Z, 4E)-hexa-2, 4-diene
Ans: 4

Exp: 2-chloro-(2z, 4E)-hex a-2, 4-diene

Which is a pair of geometrical isomers?

(I) (II) (III) (IV)

29. 4

a) I and II
b) II and III
c) I and IV
d) I and III
Ans: 1

30. 4

Which of the following orders is correct for no bond resonance energy of there radicals.
a) II > III > I
b) I > III > II
c) III > II > I
d) II > I > III
Ans: 2
 Stability of free radical increases with increasing no. of hyper conjugative structures.
(I) has 7 hyper conjugative structures.
Exp:
(II) has 3 hyper conjugative structures.
(III) has 4 hyper conjugative structures.