Haloalkane and Haloarenes

ANSWER KEY

1. (a) 2. (c) 3. (d) 4. (a)

5.(d) 6. (b) 7. (d) 8. (a)

9. (d) 10. (d) 11. (d) 12. (b)

13. (b) 14. (d) 15. (d) 16. (a)

17. (b) 18. (d) 19. (b) 20. (d)

21. (d) 22. (b) 23. (a) 24. (b)

25. (b) 26. (c) 27. (c) 28. (d)

29. (d) 30. (c) 31. (d) 32. (d)

33. (d) 34. (a),(b),(c),(d) 35. (a),(c),(d) 36. (a)

37. (b) 38. (c) 39. (a) 40. (a)

41.(d) 42. (a) 43. (a) 44. (a)

SOLUTIONS

SINGLE CHOICE QUESTIONS

1.

Answer: (a)
2.

Answer: (c)

3.

Answer: (d)

Solution:

due to 1,3 repulsion L.G. tendency increases so rate increases.

4.
Answer: (a)
Solution:
5.

Answer: (d)
Solution:

6.

Answer: (b)
Solution:

7.
Answer: (d)
Solution: Consider σ-bond resonance as well as inductive effect.

8.
Answer: (a)
Solution:

9.
Answer: (d)
Solution:

10.
Answer: (d)
Solution:

Prefer less steric nucleophile.

(1° carbanion > 2° carbanion) order of nucleophilicity (less steric hindered is nucleophilic)
11.
Answer: (d)
Solution:
12.
Answer: (b)

13.
Answer: (b)
Solution:
14.
Answer: (d)
Solution:

15.
Answer: (d)
Solution:
A= B = C

16.
Answer: (a)
Solution:

17.
Answer: (b)
Solution:

18.
Answer: (d)
Solution: Anti-elimination reaction.

19.
Answer: (b)
Solution:

20.
Answer: (d)
Solution:
21.
Answer: (d)
Solution:
Conceptual
22.
Answer: (b)
Solution: Reactant on dehydration give

23.
Answer: (a)
Solution: → Trans elimination

EtO– will bring about E2 elimination of the reactant. Hence we want groups which are trans to
each other.
24.
Answer: (b)
Solution:

25.
Answer: (b)
Solution: On E2 elimination, product are
Chiral with fixed configuration (E and Z)

Chiral with fixed configuration (E and Z)

26.
Answer: (c)
Solution:

27.
Answer: (c)
Solution:
28. Answer: (d)
Solution:
Conceptual
29.
Answer: (d)
Solution:

30.
Answer: (c)
Solution: Hydrolysis of –CN & substitution of –Br group takes place in given reaction.
31.
Answer: (d)
Solution:

32.
Answer: (d)
Solution:

33.
Answer: (d)
Solution:

MULTIPLE CHOICE QUESTIONS

34.
Answer: (a), (b), (c), (d)

35.
Answer: (a), (c), (d)
MATCH THE FOLLOWING QUESTIONS

36.

Answer: (a) (A) – r; (B) – q; (C) – p; (D) – p

Solution:
A gives E1cB due to bad leaving group F, carbanion will form.
B gives E1 elimination, carbocation is formed.
C give E2 elimination transition state is formed.
In D, Tertiary halide in the presence of strong base undergoes E2 elimination.

37.

Answer: (b) (A) – Q; (B) – R; (C) – P; (D) – Q

Solution:
In A, Strong base favors E2 elimination
In B, Strong base + presence of EWG favors E1cB mechanism.
In C, Ag2O Moist gives intermediate carbocation.
In D, Strong base favors E2 elimination.
38.

Answer: (c) A → (I); B → (III); C → (V); D → (VIII)

Solution: (A) Br– is best L.G. than

(B) SH– is best Nu– than MeSH

(C) Cl– is best Nu– than I– in DMSO
(D) In polar protic solvent I– is better Nu– than Cl–

39.

Answer: (a) A → R, S; B → P, Q; C → R, S; D → R, S
Solution: Bridge head halide and resonance stabilized halide do not shows SN1 and SN2.
40.
Answer: (a), 1 → A; 2 → D; 3 → E; 4 → G; 5 → I
Solution: (1) (A) Reaction faster due to 3° R – I
(2) (D) More reactive due to SN2 reaction
(3) (E) More reactive due to SN2 reaction. In polar aprotic solvent Cl– is better Nu–.
(4) (G) More reactive due to good leaving group.
(5) (I) More reactive due to resonance stabilized transition state formed.

41.
Answer: (d) A → P; B → R; C → S; D → Q
Solution: (a) Substitution takes place in only compound (P). In compound (S), HBr will be
eliminated hence elimination reaction, not substitution. Hence compound (1).
(b)Williamson ether synthesis ⇒ substitution cannot take place on benzene hence compound (R).
(c) Aq. ethanol will substitute Br– with EtO– and H+ ions released in the solution turning the
solution acidic in compound (S) Hence compound (S).
(d) In compound (R), after cleavage, positive charge will be on benzene -ring which is highly
unstable. Hence compound (Q).
42.
Answer: (a) A → P, R; B → P, R; C → P, R; D → Q, R
Solution:
A.

B.

C.

D.

43.
Answer: (a) A → P; B → Q; C → S; D → R
A: Dehydration of alcohol involved intermediate carbocation, so E1 mechanism.
B: In the presence of strong base alkyl chloride undergoes elimination by E2 mechanism.
C: In the presence of electron withdrawing group and strong base intermediate carbanion will
form which undergoes elimination by E1cB mechanism.
D: Cope elimination takes place by Ei mechanism (Syn elimination). Hoffman product will form.

44.
Answer: (a) A → P, Q; B → P, Q; C → Q; D → R
Solution:
A.
B.

C.

D. Violation of bredt’s rule.

SUBJECTIVE CHOICE QUESTIONS

45. Solution:

46.

Solution:

47.
Answer: 2.00
Solution:
48.

Answer: 8
Solution:
X = 3 [Hoffman alkene + saytzaff alkene (Cis/ trans)],
Y = 3 [Hoffman alkene + saytzaff alkene (Cis/ trans)],
Z = 2 one type of alkene is formed, which can give geometrical isomerism,
P=0⇒3+3+2+0=8
49.

Answer: (004)
Solution: