ALKYL HALIDE
Question 1:
Options:
(a)
(b)
(c)
(d)
Question 2: An organic compound A (C7H6Br2) gives a pale yellow ppt with warm alc.
AgNO2 solution. A on treatment with dil. KMnO4 gives a compound B (C7H5O2Br). B on
treatment with AgOH followed by heating with Br2/CCl4 gives a compound of which only
two mono nitro isomers are possible. A upon treatment with LiAlH 4 gives C (C7H7Br).
C Mg
ether
I. HCHO
II.H3O
PCC
X
The product ‘X’ would be
Options:
(a)
(b)
(c)
(d)
Question 3: Which of the two stereoisomers of 4-ter.butylcyclohexyl iodide (127 I–) will
undergo SN2 substitution with 128 I– faster, and why?
Options:
(a) A will react faster because it is the more stable of the two isomers
(b) A will react faster because it will yield a more stable product, and the transition state for
both reactions is of the same energy
(c) A will react faster because the approach of 128 I– can depart unhindered.
(d) B will react faster because it is less stable than A, and the transition state for both
reactions is of the same energy
Question 4: Identify products of the given reactions:
Options:
(a)
(b)
(c)
(d)
5. Question
Which of the following products can be obtained from above reaction?
Options:
(a)
(b)
(c)
(d) All of these
6. Question
Product (B) is:
Options:
(a)
(b)
(c)
(d)
Options:
(a) A > B > C
(b) A > C > B
(c) B > C > A
(d) B > A > C
7. Question: The decreasing order of reactivity of the compounds given below towards
solvolysis under identical conditions is:
Options:
(a) II > III > I
(b) I > II > III
(c) III > II > I
(d) II > I > III
8. Question:
Product (A) is:
Options:
(a)
(b)
(c)
(d) None of these
9. Question: Product(s) formed during this reaction is/are:
[C * = isotopic carbon]
Options:
(a)
(b)
(c)
(d) Both (a) & (b)
10. Question: End product (P) of the below reaction is:
Options:
(a)
(b)
(c)
(d)
11. Question: Most reactive compound toward SN1 is
Options:
(a)
(b)
(c)
(d)
12. Question:
Options:
(a)
(b)
(c)
(d)
13. Question :
Product of above reaction will be:
Options:
(a)
(b)
(c)
(d)
14. Question:
Product obtained in above reactions (1), (2) & (3) is:
Options:
(a) A = B but C is different
(b) A = C, but B is different
(c) B = C, but A is different
(d) A = B = C all product are identical
15. Question:
Product obtained in above reactions (1), (2) & (3) is :
Options:
(a) A = B, C is different
(b) A = C, B is different
(c) B = C, A is different
(d) A = B = C is same
16.Question: In the dehydrohalogenation of 2-bromobutane; which conformation leads to the
formation of cis-2-butene?
Options:
(a)
(b)
(c)
(d)
17.Question:
Product (B) of given reaction is:
Options:
(a)
(b)
(c)
(d)
18.Question: The E2 product of the following reaction will be?
Options:
(a)
(b)
(c)
(d)
19. Question: End product (D) in the given sequence is:
Options:
(a)
(b)
(c)
(d)
20. Question:
x and y mole consumed.
Value of x y
Options:
(a) 5
(b) 6
(c) 7
(d) 8
21. Question: The following bimolecular elimination reaction (E 2) is carried out with
different halogen leaving groups. The per cent yield of the two products (2-hexene and 1-
hexene) for each leaving group is listed below.
Which of the following statement is (are) true concerning this series of E2 reactions?
Options:
(a) Based on the pKa 's of the conjugate acid, I– is the best leaving group and F– is the poorest
leaving group
(b) When I–, Br– and Cl– are used as leaving groups, Zaitsev's rule is followed
(c) F– is the strongest base (and therefore the poorest leaving group) and the transition state
for reaction with fluoride as the leaving group has the least double bond character
(d) a, b, c are true
22. Question :
Stereochemistry of the product is:
Options:
(a) Meso compound
(b) Racemic mixture
(c) Diastereomer
(d) Optically pure enantiomers
23. Question:
Which of the following reactant is used to obtain above compound (A). (Assume that EtO – is
used in all the reaction)
Options:
(a)
(b)
(c)
(d)
24. Question :
Major product of the reaction is
Options:
(a)
(b)
(c)
(d) None of these
25. Question:
Options:
(a) 2
(b) 4
(c) 6
(d) 8
26. Question :
Product (A) is
Options:
(a)
(b)
(c)
(d)
27. Question: Under the specified conditions, substrate X undergoes substitution and
elimination reactions to give products A – D. A and B are stereoisomers, but not enantiomers.
C and D are enantiomers. A is not an isomer of C. Which of the following could be the
starting material X?
X H2O
A B C D
Options:
(a) I
(b) II
(c) III
(d) IV
28. Question: Rate limiting SN1 follows the sequence
True statement about sequence on the basis of assumption that R contains 3 different groups
is:
Options:
(a) more stable carbocation, greater is the proportion of racemization
(b) the more nucleophilic the solvent greater in the proportion of inversion
(c) In above sequence (b) represent separately solvated, pair of ions
(d) All of these
29. Question: In the given pair of alcohols, in which pair second alcohol is more reactive
than first towards hydrogen bromide?
(a)
(b)
(c)
(d)
30. Question: Which is the major product of the following reaction?
Options:
(a)
(b)
(c)
(d)
31. Question: What sequence of reagents is required to accomplish the following
transformation?
Options:
(a) (1) NBS, ROOR (2) CH3CH2O– (3) 2HBr (4) NH2– (5) disiamyl borane (6) H2O2,OH–
(b) (1) Cl2, hv (2) OH–, heat; (3) 2HCl (4) OH–, heat (5) dil.H2SO4
(c) (1) NBS, ROOR; OH–, DMSO
(d) (1) Br2, hv (2) t-butoxide (3) BH3, THF (4) H2O2, OH–
32. Question: Which of the reagents shown below would accomplish the following
transformations?
Options:
(a) A → H3O+; B → BH3 – THF; H2O2/NaOH
(b) A → NaOH; B → BH3 – THF; H2O2/NaOH
(c) A → HBr in ether; B → Hg(OAc)2/H2O; NaBH4
(d) A → NaNH2; B → Hg(OAc)2/H2O; NaBH4
33. Question: In solvolysis of 1,2-dimethyl propyl p-toluene sulfonate in acetic acid at 75°C,
how many (alkene + substitution) products will be formed?
Options:
(a) 2
(b) 3
(c) 4
(d) 5
MULTIPLE CHOICE QUESTIONS
34. Question: Correct statement(s) for the product(s) of following reaction.
CH 2 CH CH 2 Ph
Cl2 /500C
Options:
(a) Four different products are formed
(b) Two optically active products are formed
(c) The optically active compound formed here can also be made by the reaction of HCl
(d) The reaction path is free radical substitution.
35. Question: Which of following will give syn-elimination
Options:
(a) CH3CH2CH2–OCOCH3
(b)
(c)
(d)
36. Question: Match the List I (reaction) with List II (reaction intermediate) and select the
correct answer using the codes given below the Lists.
List I List II
alc . KOH /
CF3 CHCl2 CF2 CCl2 (p) Transition state
(a)
(b) (q) Carbocation
CH 3 CH 2 Br
alc. KOH
CH 2 CH 2 (r) Carbanion
(c)
(d) (s) Free radical
Options:
(a) (A) – r; (B) – q; (C) – p; (D) – p
(b) (A) – p; (B) – q; (C) – r; (D) – s
(c) (A) – s; (B) – r; (C) – q; (D) – p
(d) (A) – r; (B) – s; (C) – p; (D) – q
37. Question: Match the following
List-I List-II
(A) (P) E1
(B) (Q) E2
(C) (R) E1cb
(D) (S) Ei
Options:
(a) (A) – P; (B) – Q; (C) – R; (D) – S
(b) (A) – Q; (B) – R; (C) – P; (D) – Q
(c) (A) – Q; (B) – R; (C) – P; (D) – S
(d) (A) – R; (B) – S; (C) – P; (D) – Q
38. Question: Consider the nucleophilic attacks given below. Select in each pair that shows
the greater SN2 reaction rate.
Options:
(a) A → (I); B → (IV); C → (VI); D → (VIII)
(b) A → (II); B → (III); C → (V); D → (VIII)
(c) A → (I); B → (III); C → (V); D → (VIII)
(d) A → (I); B → (III); C → (V); D → (VII)
39. Question: Match the following.
Column I Column II
Compound Type of reaction
P. SN1 reaction can take place
A.
Q. SN2 reaction can take
place
B.
R. SN1 is not possible
C.
S. SN2 is not possible
D.
Options:
(a) A → R, S; B → P, Q; C → R, S; D → R, S
(b) A → P, S; B → P, Q; C → R; D → R, S
(c) A → R; B → P, Q; C → R, S; D → R, S, Q
(d) A → R, S; B → P, Q, R; C → R, S, Q; D → R, S
40. Question: Select which reaction from the following reaction pairs will occur faster.
Part and Reaction, respectively are
Options:
(a) 1 → A; 2 → D; 3 → E; 4 → G; 5 → I
(b) 1 → B; 2 → D; 3 → F; 4 → G; 5 → I
(c) 1 → A; 2 → C; 3 → E; 4 → G; 5 → J
(d) 1 → B; 2 → D; 3 → F; 4 → G; 5 → J
41. Question: Choose the one compound within each set that meets the indicated criterion :
Compound I Compound II
A. The compound that reacts with alcoholic
KOH to liberate Halide ion through
substitution reaction
P.
B. The compound that cannot be prepared by
a Williamson ether synthesis.
Q.
C. The compound that gives an acidic
solution when allowed to stand in aqueous
ethanol.
R.
D. The ether that cleaves more rapidly in HI.
S.
Options:
(a) A → S; B → R; C → S; D → P
(b) A → P; B → Q; C → S; D → S
(c) A → P; B → Q; C → R; D → S
(d) A → P; B → R; C → S; D → Q
42. Question: Match the column:
Column I Column II
P. Optically active product
A.
Q. Optically inactive product
B.
R. 2nd order reaction
C.
S. unimolecular reaction
D.
Options:
(a) A → P, R; B → P, R; C → P, R; D → Q, R
(b) A → P, Q; B → P, S; C → P, R; D → Q, R
(c) A → P, R; B → P, R; C → P; D → Q, S
(d) A → P; B → P, R; C → P; D → Q, R
43. Question : Match the column:
Column I Column II
P. E1
A.
Q. E2
B.
C. R. Ei (elimination intramolecular)
S. E1CB
D.
Options:
(a) A → P; B → Q; C → S; D → R
(b) A → P; B → Q; C → Q; D → S
(c) A → P; B → Q; C → R; D → S
(d) A → P; B → Q; C → Q; D → R
44. Question: Match the column (I) and (II).
Column I Column II
Reaction Comment on product
P. Racemic mixture
A.
Q. Major product consist of even number of
α-hydrogen
B.
R. Will not undergo dehydration
C.
S. Major product consist of odd number of α-
hydrogen
D.
Options:
(a) A → P, Q; B → P, Q; C → Q; D → R
(b) A → P, Q; B → P, R; C → Q, S; D → R
(c) A → P; B → P, Q; C → Q; D → R, S
(d) A → P, Q; B → P, Q; C → Q, R; D → R, S
45. Question :
What are (A) and explain their stereochemistry.
46. Question: A hydrocarbon C8H10 (A) on ozonolysis gives compound C4H6O2 (B) only.
The compound (B) can also be obtained from the alkyl bromide C3H5Br (C) upon treatment
with magnesium in dry ether followed by CO2 and acidification. Identify (A), (B) and (C) and
also give equations for the reactions.
47. Question : How many (x) moles of HI consumed?
48. Question : Sum of X + Y + Z + P =
49. Question : How many organic compounds are formed in the reaction ?
