ORGANIC CHEMISTRY

(JEE-ADVANCED)

GENERAL ORGANIC CHEMISTRY (GOC) CPP-2

1. Match the column
Column-I Column-II
(Intermediate species)
(I) (II) (III)
  
(A) Me CH2 Me3C Me2CH (P) I > III > II
  
(B) Me CH2 Me2CH Me3C (Q) II > III > I
  

(C) (R) I > II > III

(S) III > I > II

Single Correct :
2. Statement-I : A tertiary carbocation is more stable than a secondary carbocation which is
more stable than a primary carbocation.
Statement-II : The inductive effect operates through -bonds and decrease rapidly with
increase in distance.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for
statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for
statement-1.
(C) Statement-1 is false, statement-2 is true.
(D) Statement-1 is true, statement-2 is false.
3. Which order is incorrect for stability ?
 
(A) 
  CH3–CH2 (B)  

Cl Cl Cl
  
(C) H2C–CH2 > H2C–CH2 > H2C–CH2 (D)  

NO2 CN CH3
4. Which order is not correct for stability of resonating structures..

CH2 CH2

(A) 
< (B) <
C  C 
O H O H OCH3 O–CH3

 
(C) H3C–C=N–CH3 > H3C–CN–CH3 (D) 
<

 

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5. Which of the following is correct order of resonance energy?
(A) < (B) >

(C) < (D) >

N
N
H
6. Which of the following is not a valid resonating structure?
 H
N
H

CH–CH=CH2
(A) (B)

 N
(C) NH3 (D) C

Paragraph for question nos. 7 to 9

Resonance is a kind of interaction between  orbitals of a compound, which effects bond
length. Interacting  bond orbitals must be in conjugation. The bond length between C2 and
C3 in acryl aldehyde is not equal to the bond length between carbons of ethene because in
acryl aldehyde double bond is in conjugation, so it show the resonance which results the
increase in bond length between C2 and C3 in acryl aldehyde.
 
CH2=CH–CH = O CH2–CH=CH–O
(3) (2) (1) (3) (2) (1)
 
Resonance CH CH2 CH2 O
2
Hybrid (3) (2) (1)
7. Which compound will not show the resonance?
NH2

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

8. Which compound does not have the conjugative system to show the resonance?

(A) CH2=CH–CC–CH2–CH3 (B)


CH2

(C) (D)
O
9. Find out the correct statement(s) about the given compound?
8 1
7 2
6 3
5 4
(A) Bond length between C2 and C3 = Bond length between C5 and C6
(B) Bond length between C1 and C2 = Bond length between C6 and C7
(C) Bond length between C6 and C7 < Bond length between C3 and C4
(D) Bond length between C2 and C3 < Bond length between C3 and C4

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One or more than one correct :
10. Which of the following reaction will form stable ion.
Br
Ph Ph
 
(A) + aq. AgNO3  (B) + 2K  
Ph Ph
Br
O
O
(C) + HBr 
 (D) HBF4 

OH
11. Which of the following are incorrect.
(A) Order of heat of hydrogenation C–C=C–C–C–C=C–C < C–C–C=C–C=C–C–C
(B) Order of heat of combustion > > >


(C) Order of stability of carbocation > >

N N N

(D) Order of heat of combustion cis-1,4-bis-(t-butyl) cyclohexane<Trans-1,4-bis-(t-butyl)

cyclohexane
Match the column
12. Column-I Column-II

(A) (P) Planar

(B) (Q) Non-planar

N

(C) (R) (4n + 2)  electron

(D) (S) (4n)  electron

Paragraph for Question Nos. 13 to 15

Aromatic compound are these that meet the following criteria :
(i) The structure must be cyclic, containing (4n + 2) electrons
(ii)Each atom in the ring must have unhybridized p-orbitals
(iii) Unhybridized p-orbitalmust overlap orbitals.
(iv) Structure must be planar
In anti-aromatic compound (4n) electron are delocalization, but delocalization of pi electrons
over the ring increases the electronic energy.
13. Which of following compound is aromatic?
 H   H 
N N H–N N H–N N–H H–N N–H
H H
(A) (B) (C) (D)

14. Which of following is anti aromatic?

(A) (B) (C) (D) All
O

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15. In which of following reaction product formed is aromatic?
OH
OH
H H KH
(A)  (B)  (C)  (D) All

16. Which of the following is the correct order of bond energy for indicated C=C bonds?

  
(x) (y) (z)
(A) x > y > z (B) z > y > x (C) z > x > y (D) None of these
Paragraph for question nos. 17 & 18
d
OH

O2N NO2
e c
H2N COOH

NO2
f b
CH3–HN SO3H
a
HO
NH–C–CH3
g
O
17. How many moles of NaHCO3 will consume on reaction with 1 mole of this compound?
(A) 2 (B) 3 (C) 4 (D) 1
18. What is the correct order of basic strength of the following?
(A) e > f > g (B) f > e > g (C) g > e > f (D) e > g > f
19. Correct order of decreasing basic strength of the given compound is.

(I) (II) Et–N–Et (III) (IV)

N Et N N

(A) IV > III > II > I (B) I > II > III > IV (C) IV > III > I > II (D) I > II > IV > III
One or more than one correct :
20. Select correct options.
NH2 NH2
Me
(A) basicity (B) < basicity
<
N N
COOH COOH OH OH
Me
(C) < acidity (D) < acidity

ANSWER KEY
1. A  Q; B  R; C  P 2. (A) 3. (C) 4. (C)
5. (D) 6. (C) 7. (B) 8. (D) 9. (B)
10. (ABD) 11. (ABCD) 12. (A)  P, R; (B) P, R; (C) Q,R; (D) Q,S
13. (C) 14. (A) 15. (D) 16. (C) 17. (A)
18. (B) 19. (D) 20. (BCD)
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