CHEMISTRY (HYDROCARBONS)

SINGLE CHOICE QUESTIONS

Question 1: An isomer of C5H12 gives total six isomeric products on monochlorination.

Calculate the percentage yield of the primary monochloride which is chiral. Consider the
following relative reactivity of C – H bonds for chlorination.
Degree of C–H 1o C–H 2o C–H 3o C–
H
Relative reactivity for chlorination (RR) 1 3 5
Options:
(a) 26.8%
(b) 25%
(c) 30%
(d) 50%

Question 2: The typical reaction of benzene and other aromatic compounds are electrophilic
substitution. Presence of electron donating group activates the ring towards electrophilic
substitution, while presence of electron withdrawing group deactivates the ring towards
electrophilic substitution but at the same time activates the ring towards nucleophilic
substitution. Some groups are predominantly meta-directing and all of these are deactivating.
Except halogen, most of the o-and p-directing groups are activating groups.

D and E are:
Options:
(a)

(b)
(c)

(d)

Question 3:

Options:
(a)

(b)
(c)

(d)

Question 4:

The compound (S) is :

Options:
(a)

(b)

(c)
(d)

Question 5: Which steps is used to produce 1–Chloro–3–ethylbenzene

Options:
(a)

(b)

(c)

(d)

Question 6:

Options:
(a)
(b)

(c)

(d)

Question 7:

The compound ‘P’ is:

Options:
(a)

(b)

(c)
(d)

Question 8: The end product of following reaction is :

Options:
(a) Benzyl alcohol
(b) Benzene carbaldehyde
(c) Benzoic acid
(d) Benzophenone

Question 9: Among the following free radical bromination reactions, select those in which 2 o
halide is the major product-

Options:
(a) P, Q, R, S
(b) P, R, U
(c) P, R, S, T
(d) P, Q, R, S, T

Question 10: Which of the following bromides is the major product of the reaction shown
below, assuming that there are no carbocation rearrangement?

Options:
(a)
(b)

(c)

(d)

Question 11: Which of the following reactions results in the formation of a pair of
diastereomers?
Options:
(a)

(b)

(c)

(d)

Question 12:
Product (A) of the reaction is:
Options:
(a)

(b)

(c)

(d)

Question 13: Di-imide (N2H4) is used to reduce double bond of:

Options:
C  O
(a) |
(b) C  N
 NO
(c) 2

(d) CH  CH 

Question 14:
Compound A is
Options:
(a)

(b)

(c)

(d)

Question 15:

Product (A) is:

Options:
(a)

(b)
(c)

(d)

Question 16: Which of the following compound was the starting material for the oxidation
shown below?

Options:
(a)

(b)

(c)

(d)

Question 17:
Options:
(a)

(b)

(c)

(d)

Question 18: In which of the following reactions 1,3-butadiene will be obtained as a major
product?
Options:
CH3  COK  2 mole 
Br  CH 2  CH 2  CH 2  CH 2  Br 
 CH3 3 COH 
(a)
(b) HO  CH2  CH2  CH2  CH2  OH  
conc. H2 SO4

2 
H 2C  CH  C  CH  
H 1 mole
Ni2 B
(c)
(d) All of these

Question 19: Predict the major product of the reaction.

(a)

(b)
(c)

(d)

Question 20:

Product (A) is:

Options:
(a)

(b)

(c)

(d)

Question 21:
Major product of the reaction is:
Options:
(a)

(b)

(c)

(d)

Question 22:

End product of the reaction is:

Options:
(a)

CH3  CH  CH  CH  CH 2
(b)
H 2C  CH  CH  CH 2
(c)
(d)
H 2C  CH  CH 2  CH  CH 2

Question 23:

Major product of the reaction is:

Options:
(a)

(b)

(c)

(d)

Question 24: which alkyne will give 3-ethylhexane on catalytic hydrogenation?

Options:
(a)

(b)

(c)
(d) All of these

Question 25: Which combination is best for preparation of the compound (A) shown below?

Options:
(a)

(b)

(c)

(d)

Question 26: What is the product, C, of the following reaction sequence?

Options:
(a)
(b)

(c)

(d)

Question 27: Compound

Compound (X) will be:

Options:
(a)

(b)

(c)
(d)

Question 28: In which reaction last product is Ph – C ≡ CH?

Options:
(a)

(b)

(c)

(d) All

Question 29: The best sequence of reactions to prepare 2-heptanone is:

Options:
n  C4 H9 Br H2 O , Hg 2
NaNH2
 X  Y  H 2 SO4

(a) Propyne
n  C5 H12 Br H 2 O , Hg 2
NaNH 2
 X  Y  H 2 SO4

(b) ethyne
H 2 O , Hg 2
NaNH 2
 X  CH 2 Br
Y  H 2 SO4

(c) 1-hexyne
H 2 O , Hg 2
NaNH 2
 X  C2 H 2 Br
Y  H 2 SO4

(d) 1-pentyne

Question 30: Identify the end product in the given sequence of reaction

Options:
(a)
(b)

(c)

(d)

Question 31: Statement-1: In strongly acidic medium aniline becomes more reactive towards
electrophilic substitution reaction
Statement-2: In strongly acidic medium second substituent enters m-position of NH2 in aniline
Options:
(a) Statement 1 is True, Statement 2 is True; Statement 2 is a correct explanation for Statement1
(b) Statement 1 is True, Statement 2 is Tue; Statement 2 is NOT a correct explanation for
Statement 1.
(c) Statement 1 is True, Statement 2 is False
(d) Statement 1 is False, statement 2 is True.

Question 32:

Predict the major product:

Options:
(a)

(b)
(c)

(d)

Question 33: Match the column

Column I Column II
(A) (P) Birch reduction

(B) (Q) Stephen’s reduction

(C) (R) Wolf-Kishner reduction

(D) (S) Clemmensen reduction

Options:
(a) (A) – (s); B – (r); (C) – (p); (D) – (r, s)
(b) (A) – (p); B – (r); (C) – (q); (D) – (s)
(c) (A) – (s); B – (r); (C) – (q); (D) – (p)
(d) (A) – (p); B – (q); (C) – (r); (D) – (s)

Question 34: Match the reaction of column (I) with the characteristics given in column (II)
Column-I Column-II
(A) (p) Formation of carbocation
intermediate

(B) (q) Six membered ring closure in

intramolecular reaction

(C) (r) Aromatic Electrophilic substitution

(D) (s) Dehydrogenation reaction

(t) 5-membered ring closure in

intramolecular reaction
Options:
(a) (A) – p, q, r; (B) – p, q, r, s; (C) – p, q, r, s; (D) – p, r, t
(b) (A) – p, q, r, s; (B) – p, q, r; (C) – p, q, s; (D) – p, r, s
(c) (A) – p, q, s; (B) – p, q, r; (C) – p, q, r, t; (D) – p, q, t
(d) (A) – p, q, t; (B) – p, q, r, t; (C) – p, q, r, s; (D) – p, s, t

Question 35: Match the column

Column-I Column-II

DilH 2 SO4
Hg 2
 (p) 1–phenylbutan-1-one
(A) 1-Phenylbut -1-yne
(B) 1-Phenylbut -1-yne (q) 1–Phenylbutan-2-
 3 1 BH THF

 2 H O OH
 one
2 2

Br2  CCl4
(C) But-2-ene (cis)   (r) Syn addition
Br2  CCl4
(D) But-2-ene (trans)   (s) Anti addition
(t) Optically inactive
Options:
(a) (A) – p, t; (B) – q, t; (C) – s, t; (D) – s, t
(b) (A) – p, q; (B) – q, t; (C) – s, t; (D) – r, s
(c) (A) – p, t; (B) – q, r; (C) – r, s; (D) – s, t
(d) (A) – q, t; (B) – s, t; (C) – r, s; (D) – s, t

MULTIPLE CHOICE QUESTIONS

Question 36: Which of the following compounds will give same major product on acid catalysed
hydration
Options:
(a)

(b)

(c)

(d)

Question 37: The correct products have been reported in reactions.

Options:
(a)

(b)

(c)

(d)

Question 38: Acetone (CH3COCH3) is the major product in:

Options:
(a) I
(b) II
(c) III
(d) none

Question 39: Which of the following is/are correct statement?

Options:
(a) Antiaromatic compounds are paramagnetic in nature
(b) The rate of nitration – C6H6 > C6D6 > C6T6
(c) The rate of sulphonation − C6H6 > C6D6 > C6T6
(d) Anthracene gives three monochloro products on chlorination

Question 40: Which of the following reactions are less possible by Friedel-craft’s acylation as
per expectation?
Options:
(a)

(b)

(c)

(d)

SUBJECTIVE CHOICE QUESTIONS

Question 41: Find out reagents involved in following conversions:

Question 42: 2-Butyne undergoes following reactions in steps as indicated. Identify A to H.

Question 43: Identify A, B, C with proper explanation.

Question 44: A hydrocarbon A(C10H12) has no chiral carbon. A gives a white precipitate with
ammonical solution of silver nitrate. A on treatment with H 2/Pt gives B(C10H20). A on ozonolysis
gives C(C8H12O4) as one product which on heating with soda lime gives D(C6H12). D on
monochlorination with Cl2/hv gives C6H11Cl as sole isomer. Identify A to D.
Question 45: C5H10 represents three isomeric alkenes A1, A2 and A3. Each on hydrogenation
gives 2-methylbutane. A1 and A2 on oxymercuration-demercuration give the same 3º alcohol. A2
and A3 on hydroboration oxidation give different 1º alcohol. Assign structures to A1, A2 and A3
and explain the reactions.

Question 46: One of the constituent of turpentine is  -pinene having molecular formula C10H16.
The following scheme give reaction of  -pinene. Determine the structure of  –pinene & of the
reaction products A through E.

Question 47: Propose structures for intermediates & products A to G

Question 48: Identify the following (A to D).

Question 49: Write the structural formula of limonene from the following observation:
(a) Limonene when treated with excess H2 & Pt catalyst, the product formed is 1- isopropyl - 4
methyl cyclohexane
(b) When it is treated with O3 & then Zn/H2O the products of the reaction are HCHO &
following compound

Question 50: Compound A (C6H12) is treated with Br2 to form compound B (C6H12Br2). On
treating B with alcoholic KOH followed by NaNH 2 the compound C(C6H10) is formed. C on
treatment with H2/Pt forms 2-methylpentane. The compound ‘C’ does not react with ammonical
Cu2Cl2 or AgNO3. When A is treated with cold KMnO4 solution, a diol D is formed which gives
two acids E and F when heated with KMnO4 solution. Compound E is found to be ethanoic acid.
Deduce the structures from A to F.

Question 51: What are D to G for the following reactions

Question 52: What reagents would be required to carry out the following synthesis ?

Question 53: An organic compound (A) (m.f. = C7H12O2) on heating with sodalime produces
(B) (m.f. = C6H12). (A) on reduction with P/HI produces (C) (m.f. = C7H14) (C) has six
membered ring, on monobromination it can produce five structural isomers products. Find out
structure of (A), (B) and (C).

Question 54: From what alkene and by which method would you prepare each of the following
alcohols free of constitutional isomers (structural isomers).
(a) (C2H5)3C – OH
(b)

(c)

Question 55: Write the structure of the products formed in the following SE reactions :
(i)
(ii)

(iii)

(iv)

(v)

Question 56: Indicate the position of the electrophile in the following compounds :

Question 57: Unlike most hydrocarbons, azulene (C10H8) is highly coloured (deep blue),
although its isomer, naphthalene, does not have significant zwitter-ionic character, azulene does.
(i) Draw a resonance structure of azulene in which five-membered ring is anionic and the seven-
membered ring cationic.

(ii) Can azulene be considered aromatic ?

Question 58: Explain, which of these compounds is a stronger acid. :

Question 59: Arrange A, B, C in increasing potential energy :

Question 60: What are the major products in the following reactions :

Question 61: How many of the following reactions are possible (explain your reason) :