ORGANIC CHEMISTRY

(JEE-ADVANCED)

GENERAL ORGANIC CHEMISTRY (GOC) DPP-2

Single Correct :
1. Which of the following is correct order of stability of given carbocations?
⊕
⊕ CH2 ⊕

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

⊕
O
(A) II > I > III > IV (B) II > IV > III > I (C) I > II > III > IV (D) I > IV > II > III

2. Which one is correct order for resonance energy?

(A) < (B) Θ> Θ

⊕ ⊕

(C) < (D) <

O
3. Statement-1: is less basic than
N N
H H
Statement-2: There are three lone pairs of electrons in second compound as compared to
only one in first compound.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for
statement-1.
(B) Statement-1is true, statement-2 is true andstatement-2isNOTthe correct explanation for
statement-1.
(C) Statement-1 is true, statement-2 is false.
(D) Statement-1 is false, statement-2 is true.

N
4. (a) Et3N (b) N (c) N

Compare basic strength of following:

(A) a > b > c (B) b > a > c (C) b > c > a (D) c > b > a

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5. Select the correct statement.
NH2 NH2
CH3
(A) is more basic than

COOH COOH
CH3
(B) is less acidic than

NMe2 NMe2
CH3
(C) is more basic than

NO2 NO2
CH3
(D) has shorter C–N bond length than

6. The correct order of acidity for the following compounds is

CO2H CO2H CO2H
CO2H OH
I. HO OH II. III. IV.
OH
OH
(A) I > II > III > IV (B) III > I > II > IV (C) III > IV > II > I (D) I > III > IV > II

7. The order of basicity among the following compounds is

NH NH2
I. H3C NH2 II. N NH III. HN N IV. H2N NH

(A) II > I > IV > III (B) IV > II > III > I (C) IV > I > II > III (D) I > IV > III > II

8. The correct order of acid strength of the following carboxylic acid is

O
O H OH
I. H II.
OH H
O OH
III. MeO IV. H3C
OH O
(A) III > II > I > IV (B) I > II > III > IV (C) I > III > II > IV (D) II > I > IV > III

One or more than one correct :

9. Which of the following is/are aromatic species.

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

N ⊕
O
H

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10. Which of the following represent correct order of acidic strength
CH3 Cl Br
(A) CH ≡ CH > CH2 = CH2 > CH3 – CH3 (B) OH > OH > OH

COOH COOH COOH

(C) > > (D) Me2CH–OH > Me3CH–OH > MeCH2–OH
COOH COOH COOH

11. With respect to the compounds I-V, choose the correct statement(s).

H
H
H
H-CH3 H H

I II III IV V
(A) The acidity of compound I is due to delocalization in the conjugate base.
(B) The conjugate base of compound IV is aromatic
(C) Compounds II becomes more acidic, when it has a-NO2 substituent.
(D) The acidity of compounds follows the order I > IV > V > II > III.

12. Consider the following four compounds I, II, III and IV.
H3C CH3
H3C CH3 NH2 N
NH2 N
O2N NO2 O2N NO2

NO2 NO2
I II III I
Choose the correct statement(s).
(A) The order of basicity is II > I > III > IV.
(B) The magnitude of pKb difference between I and II is more than that between III and IV.
(C) Resonance effect is more in III than in IV.
(D) Steric effect makes compound IV more basic than III.

13. 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

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

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Paragraph :
Comprehension # 1
(a)
OH
(x) (q)
H NH–Me
(w)
H(y) (b)
(p) H
H2N COOH
NH(r)
H2N NH2
(d)
H C NH2
(z) (s)
C
H
(c)

14. Which of the following is correct order of acidic strength.

(A) b > a > d > c (B) b > a > c > d (C) b > d > a > c (D) a > b > d > c

15. Which of the following is correct order of basic strength.

(A) q > s > p > r (B) r > s > q > p (C) r > q > s > p (D) q > r > s > p

Comprehension # 2
(a)
H2C–H3C CH3
(c) (e)
H NH–CH3
(f)
N
H (d)NH2 CH3
(b)
O–H C≡CH
(h) (g)

16. Which of the following is correct order of acidic strength.

(A) h > d > g (B) h > g > d (C) g > d > h (D) d > h > g

17. Which of the following is correct order of basic strength.

(A) f > e > d (B) d > f > e (C) e > f > d (D) f > d > e
Numerical value :
18. Among the following, the number of aromatic compound(s) is
⊕
Θ ⊕

⊕ Θ

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19. Among the following compounds:
(i) (ii) C8H8−2 (iii) (iv)

N
(v) (vi) (vii) (viii)
N N N
N
OH
⊕

(ix) C3H3+1 (x) (xi)

N
(a) Number of compounds which are aromatic = w
(b) Number of compounds which are non-aromatic = x
(c) Number of compounds which are anti-aromatic = y
(d) Number of compounds which readily undergo Dimerization at room temperature= z.
What is the sum of w + x + y + z.

Match the Column

20. Match the column-I with column-II. Note that column-I may have more than one matching
options in column-II.
Column-I Column-II
(stability) (Reason)

H3C ⊕ CH3
C

+
(A) > CH3 (P) Inductive effect

CH3
– –
(B) H3C–C < CH3 (Q) Resonance
CH3
CH3
+ +
(C) H3C–C > H3C–CH2 (R) Hyperconjugation
CH3
H3C
CH2 CH2
(D) > CH3 (S) Steric hindrance

ANSWER KEY
1. (C) 2. (C) 3. (D) 4. (C) 5. (C)
6. (A) 7. (C) 8. (A) 9. (ABC) 10. (AC)
11. (ABC) 12. (CD) 13. (BCD) 14. (B) 15. (C)
16. (B) 17. (A) 18. 5 19. 13
20. (A) → P, Q, R; (B) → P; (C) → P, R; (D) → Q, R

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