ALIPHATIC HYDROCARBONS

SECTION-I (Single correct option)

1. In how many of the following reactions a secondary halide is formed as a major product?
Assume that all types of primary carbons are equally reactive and same is true with all types of secondary carbons.

Cl2 Cl2
P) Q)
h h

Cl2 S) Cl2
R)
h h

Br2 U) Cl2
T)
h h
(A) Q, R, S, & T (B) Q, R, S, T & U (C) P, R, S, T & U (D) Q, S, T & U

2. On catalytic hydrogenation, how many alkenes (counting stereoisomers as well) give 2-methylpentane?
(A) 3 (B) 6 (C) 7 (D) 5

3.
X2
monohalogenated product
h
Which halogen gives the maximum yield of a monohalogenated product (the monohalogenated product may be 10, 2 0 or 30)?
(A) Cl2 (B) Br2 (C) I2 (D) Cl2 and Br2 give same yield.

4. How many monohalogenated products (counting stereoisomers as well) are obtained by halogenation of the following
compound?

(A)1 (B) 2 (C) 3 (D) 4

5.
1. 2Li 2. CuI Cl2
CH3-CH2-Cl 3. CH Br A B (major)
3 h
B is
(A) 2-Chlobutane (B) 1-Chlorobutane (C) Isopropyl chloride (D) n-Propyl chloride

6. An alkane ‘A’ (C6H 14), on photochemical chlorination, gives only three monochloro derivatives (considering only structural
isomerism). ‘A’ can be
(I) n-Hexane (II) 2-Methyl pentane (III) 3-Methylpentane (IV) 2,2-Dimethylbutane
(A) I & II (B) II & III (C) I & IV (D) III & IV

7. An alkane ‘A’ (C5H 12) can be prepared by catalytic reduction of three alkenes. The same alkane can be prepared by treating
six different alkyl halides first with Mg/dry ether and then with H2O. Considering stereoisomers as well, identify the alkane.
(A) n-Pentane (B) Isopentane (C) Neopentane (D) Cyclopentane

8. A saturated hydrocarbon burns in oxygen to give carbon dioxide and water. Approximately twice as much CO2 as H2O (by
weight) is produced by this combustion. Light induced chlorination of the hydrocarbon by 2.0 equivalents of chlorine gives a
mixture of mono-, di- and trichloro compounds, along with small amounts of higher chlorination products. Only one monochloro
isomer is formed, but there are two dichloro isomers and three trichloro isomers produced in the reaction. Which of the
following is the hydrocarbon?
(A) Neopentane (B) Isopentane (C) n-Pentane (D) Isobutane

9. 2,2,4-Trimethylpentane, on photochemical chlorination, gives four isomeric monochlorides (only structural isomers
considered). The two primary chlorides make up 65% of the total product mixture. What is the percentage of each of the
primary halides?
(A) 30 and 35 (B) 39 and 26 (C) 15 and 50 (D) 50 and 15

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10. Which of the following compounds give(s) a mixture of diastereomers on treatment with H 2/Pt?

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

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

11.
Cl

* Mg
A CH3COOD M number of isomers.
THF
If C* = C14, the value of M is
(A) 3 (B) 5 (C) 2 (D) 7

12.
HO

O CH2SH
excess CH3MgBr

CH2-COOH
C CH
The number of moles of CH 4 formed in the above reaction is
(A) 3 (B) 4 (C) 5 (D) 6

13. Which compound of each pair reacts faster with the specified reagent?
CH2 CH3

OCH3
(I) or with dil. H2SO4 O

(II) or with acid catalysed hydration

CH(CH3)2 CH(CH3)2
(A)
(A) (B) (B)

SO2Ph OSO2Ph
(III) or with KOC(CH3)3 in (CH3)3COH
CH3-CH-CH3 CH3-CH-CH3
(A) (B)

(A) I-A, II-A, III-B (B) I-A, II-B, III-B (C) I-B, II-B, III-B (D) I-A, II-A, III-A
14.
1 eq CH3COOOH
Major product is

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

O O

OH
OH
15.

H2/Pt

Total number of hydrogenated products formed in the above reaction is

(A) 1 (B) 2 (C) 3 (D) 4
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16.
HO
HO
H+ H+
P Q
 
P and Q respectively are
(A) (B)
& &

(C) (D)
& &

17. Which of the following compounds give(s) acetone as one of the products on ozonolysis?

I II III IV V
(A) I, II & V (B) I, III & V (C) I, IV & V (D) I & V
18. Correct order of reactivity of the following compounds toward HBr is

I II III

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

19.
Br2 NaOEt 1. BH3/THF
A
h EtOH/ 2. H2O2/OH-

KOC(CH3)3 1. BH3/THF
B
(CH3)3COH/ 2. H2O2/OH-
A and B respectively are

(A) OH (B)
& &

OH OH OH
(C) (D) OH
& &
OH OH
OH
20.

HCl
Major product is

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

Cl
Cl
Cl Cl

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21.
HO

H+
Major product is


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

22.
1.O3
A CH3CHO
2. Zn/H2O
C

B + PPh3 NaH
C
B is
(A) CH3Cl (B) C 2H 5Cl (C) CH3OH (D) C 2H 5OH

23. Correct order of rate of reaction of the following compounds toward dil. H2SO4 is
N
I II III
N N
(A) I > II > III (B) I > III > II (C) III > II > I (D) III > I > II

24. To which point on the potential energy diagram does the figure shown at right correspond?

25. Which of the following energy profile best represents the reaction,
H+ H3C CH3
CH3-CH2-CH=CH2
H H
(A) (B) (C) (D)

26. Which reaction conditions would best convert 3-hexyne to cis-3-hexene?

(A) Pt catalyst and H2. (B) Lindlar's Pd catalyst and H 2.
(C) Na in liquid NH 3. (D) NaNH 2 in liquid NH3.

27. Reaction of 1-hexene with NBS (N-bromosuccinimide) forms two isomeric bromohexenes, one of which is 3-bromo-1-hexene.
Which of the following is the other isomer?
(A) 1-bromo-2-hexene. (B) 6-bromo-1-hexene.
(C) 1-bromo-1-hexene. (D) 2-bromo-1-hexene.

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28. Peroxide induced reaction of carbon tetrachloride with 1-butene produces which of the following?
(A) 1,1,1,3-tetrachloropentane. (B) 1,1,1,2-tetrachloropentane.
(C) 1-chloro-2-trichloromethylbutane. ( D) 1,1-dichloro-2-ethylcyclopropane.

29. A C8H14 hydrocarbon (X) is reduced by sodium in liquid ammonia to a single C8H16 product (Y). Both of these compounds
undergo hydrogenation (Pt catalyst) to give 2,5-dimethylhexane. Ozonolysis of Y with an oxidative workup produces a single
C4H8O2 carboxylic acid. Reaction of Y with perbenzoic acid (C 6H 5CO 3H) gives a chiral C8H14O product, but reaction with
bromine gives an achiral C8H14Br2 product. What are X and Y?
(A) X is 2,5-dimethyl-3-hexyne ; Y is cis-2,5-dimethyl-3-hexene.
(B) X is 2,5-dimethyl-3-hexyne ; Y is trans-2,5-dimethyl-3-hexene.
(C) X is 2.5-dimethyl-1,5-hexadiene ; Y is 2,5-dimethyl-3-hexyne.
(D) X is 2,5-dimethyl-2,4-hexadiene ; Y is cis-2,5-dimethyl-3-hexene.

30. What is the relative rate of addition of HBr to I: 1,3-pentadiene; II: 1,4-pentadiene; and III: 1-pentyne?
(A) I > II > III. (B) III > II > I. (C) II > I > III. (D) III > I > II.

31. A chiral C 6H 12 hydrocarbon undergoes catalytic hydrogenation to yield an achiral C6H14 product. What is the starting
compound?
(A) cis-2-hexene (B) 3-methyl-2-pentene
(C) 4-methyl-2-pentene (D) 3-methyl-1-pentene

32. Reaction of 3,3,6,6-tetramethyl-1,4-cyclohexadiene, first with excess aqueous mercuric acetate, then followed by sodium
borohydride reduction, produces a mixture of isomeric C10H 20O2 alcohols.
Including enantiomers, how many isomeric products may be formed in this reaction?
(A) 2 (B) 4 (C) 6 (D) 8

33. A C8H12 chiral hydrocarbon, X, is reduced by catalytic hydrogenation to an achiral C8H14 compound. Ozonolysis of X (H2O2
workup) gave a chiral C 8H12O4 dicarboxylic acid. Which of the following could be X?
(A) (B) (C) (D)

34. Which of the following reactions of cyclohexene may be considered an oxidation?

(A) addition of hydrogen (Pt catalyst) to give cyclohexane.
(B) addition of HBr to give bromocyclohexane
(C) epoxidation by perbenzoic acid to give cyclohexene oxide
(D) mercuric acetate catalyzed hydration to give cyclohexanol

35.. Addition of HBr to 2,3-dimethyl-1,3-cyclohexadiene may occur in the absence or presence of peroxides. In each case two
isomeric products are obtained. Which of the following is a common product from both reactions?

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

Br

36. Which of the following isomers has the lowest heat of combustion?
A) cis-1,2-dimethylcyclohexane B) trans-1,2-dimethylcyclohexane
C) cis-1,3-dimethylcyclohexane D) trans-1,3-dimethylcyclohexane
37. The nitrogen atom in each of the following tertiary amines may be removed as trimethyl amine by repeated Hofmann
eliminations (exhaustive methylation followed by heating with AgOH). Which of the amines requires the greater number of
Hofmann sequences to accomplish this?
(A) (B) CH3 (C) N(CH3)2 (D) CH3
N N N

38. Only one of the following amines will lose its nitrogen atom as trimethyl amine by repeated Hofmann elimination reactions
(exhaustive methylation followed by heating with AgOH). Identify that amine.
(A) (B) (C) CH3 (D)
N
N
N
N
CH3

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39. Compare the rate of dehydration of A, B & C by conc.H2SO 4.

OH OH

OH
B C
A

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

40. In the dehydrohalogenation of 2-bromobutane, which of the conformations leads to the formation of cis-2-butene?

(A) CH3 (B) CH3 (C) CH3 (D) CH3

H CH3 H CH3 H H H3C H

H Br Br H Br H H Br
H H CH3 H

41. The following compound is subjected to ozonolysis.

CH3
I.O3 II.Zn/H+
 
CH3

The following are the stereoisomers of the ozonolysis product.

CHO CHO CHO

H H H H H H
H H CH3 C) H CH3
A) CH3 B)
H CH3 CH3 H H CH3

H H H H H H

CHO CHO CHO

Which of the above(A or B or C) is/are actually obtained in the above reaction ?

(A) Only A (B) Only B (C) A & B in equal amounts (D) Only C
42.

I II III IV

Heats of hydrogenation of the above compounds are in the order

(A) I < II < III < IV (B) I < III < II < IV (C) I < III < IV < II (D) II < I < III < IV
43.
H+ Br2
P (A mixture) Q (A mixture)
 CCl4
OH
If P contains 3 products, how many products does Q contain?
(A) 3 (B) 5 (C) 4 (D) 6
44.

Above conversion can be achieved by

(A) I. O3; Zn/H 2O II. Zn-Hg; HCl (B) I. H+ II. O3; Zn/H2O III. Zn-Hg; HCl
(C) I. H+ II. O 3; Zn/H2O III. LiAlH 4 (D) I. HBr II. O3; Zn/H 2O III. LiAlH4

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45. Which of the following alkyl halides can’t be prepared by adding HBr (with or without H 2O2) to an alkene?

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

Br

Br
46. What is the major product of the following reaction?
H+

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

47. Identify Z in the following sequence of reactions.

1.B2H6; THF conc. H2SO4 dil. H2SO4
X Y Z
2. H2O2,OH-  

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

OH
OH

OH
OH
48.
COONa
electrolysis
Final product of the reaction is

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

49. Which of the following on ozonolysis (O 3 followed by Zn/H2O) gives only two different products?
`
(A) (B) (C) (D)

50. Total number of ozonides (including stereoisomers) formed when 2-pentene (cis or trans) is treated with O3 is
(A) 6 (B) 3 (C) 10 (D) 8
51. Among the following compounds, which liberates two equivalents of CO2 when treated with hot KMnO4?

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

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SECTION-II (More than one correct option)

52.

OH
OH
Select the correct option(s)
(A) The above conversion can be achieved by i. H+/  , ii. BH3/THF followed by H2O2/OH-.
(B) If the conversion is done as given in the option A, only trans isomer of the product is obtained.
(C) If the conversion is done as given in the option A, only cis isomer of the product is obtained.
(D) The above conversion can be achieved by i. H +/  , ii. CH 3COOOH ; H+.

53. Which of the following reactions result(s) in the formation of racemic mixture?

HBr
HBr
(A) (B) CH3COOH
CH3COOH

(C) HBr (D) HBr

CH3COOH CH3COOH
54.

H+ H+
 

OH OH
Select the correct statement(s) about the two reactions.
(A) First reaction gives a mixture of enantiomers while the second one gives a mixture of diastereomers.
(B) Both reactions give a mixture of enantiomers.
(C) First reaction is faster than the second.
(D)Both reactions give a mixture of diastereomers
55.
cold alk. KMnO4 cold alk. KMnO4

Select the correct statement(s) about the two reactions.

(A) First reaction gives a mixture of enantiomers while the second gives a pure optically inactive compound.
(B) First reaction gives a mixture of diastereomers while the second gives a pure optically inactive compound.
(C) First reaction gives a mixture of enantiomers while the second gives a mixture of diastereomers.
(D) Both products have two chiral centers each.
56. Which of the following alkenes give same product when treated separately with dil. H 2SO4 and Hg(OAc)2/H2O; NaBH4?

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

SECTION-III
Passage-I
One liter of 0.1 M CH 3COONa is electrolysed in Kolbe’s electrolytic method until the entire amount of acetate ions is
consumed.
Assumptions: 1. Hydrogen, ethane and CO 2 are insoluble in water.
2. Do not consider disproportionation reactions.
57. What is the PH of the solution after electrolysis?
(A) 13 (B) 1 (C) 6.2 (D) 11.8

58. What is the total volume of the gases evolved at STP (at both the electrodes together) during electrolysis.
(A) 2 L (B) 2.24 L (C) 6.72 L (D) 4.48 L
Passage-II
Enantiomers cannot be separated from each other by fractional distillation or fractional crystallization or chromatography, since
they have identical physical properties. As a result, when a mixture of enantiomers is subjected to fractional distillation, the
mixture comes out as a single fraction. As diastereomers have different physical properties, they can be separated by any of
the above mentioned techniques.

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59.
Cl2
2-Methylbutane P (number of monochloro products)
h
Fractional distillation

Q (Number of fractions, out of which R is the number of fractions

which are optically active)
The values of P, Q and R are
(A) 5, 4, 2 (B) 5, 4, 1 (C) 6, 4, 2 (D) 6, 4, 0

60.
Cl2
3-Methylpentane P (number of monochloro products)
h
Fractional distillation

Q (Number of fractions, out of which R is the number of fractions

which are optically active)
The values of P, Q and R are
(A) 8, 5, 0 (B) 4, 3, 1 (C) 6, 3, 1 (D) 6, 5, 1
61.
Cl2
2-Methylpentane P (number of monochloro products)
h
Fractional distillation

Q (Number of fractions, out of which R is the number of fractions

which are optically active)
The values of P, Q and R are
(A) 8, 4, 0 (B) 8, 5, 0 (C) 7, 4, 1 (D) 7, 4, 2
62.
Cl2
(R)-2-Chlorobutane P (number of dichloro products)
h
Fractional distillation

Q (Number of fractions, out of which R is the number of fractions

which are optically active)
The values of P, Q and R are
(A) 5, 5, 1 (B) 5, 5, 3 (C) 5, 4, 0 (D) 4, 4, 0

Passage-III

Dil. H2SO4
C10H20O2
Terpine

Limonene

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63. Structural formula of terpine is

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

OH OH

OH OH
64. Number of stereoisomers possible for the structural formula of terpine is
(A) 2 (B) 3 (C) 4 (D) 5
65. Number of stereoisomers possible for the structural formula of limonene is
(A) 2 (B) 3 (C) 4 (D) 5

Passage-IV
C (C7H14O)

1. Hg(OAc)2/H2O
2. NaBH4

dil. H2SO4 excess H2

B (C7H14O) A (C7H12)

1. B2H6/THF
2. H2O2/OH-

D (C7H14O)
Out of A, B, C and D, only C is optically active. B, C and D on dehydration give the same product, 1-methylcyclohexene.

66. Structural formula of A is

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

67. Stereochemical formula of C is

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

HO
OH OH

68. ‘A’ on reaction with HCl/H 2O 2 gives

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

Cl
Cl

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69.
REACTION DESRIPTION OF THE PRODUCT
(A) (P) Racemic mixture
H2
Ni

(B) (Q) Meso compound

H2
Ni

(C) (R) Single enantiomer

H2
Ni

(D) (T) Diastereomers

H2
Ni

70. Compounds on the left are subjected to photochemical chlorination with Cl2/hv. Number of chloroderivatives (including
stereoisomers) obtained are given on the right. Match them correctly.

(A) n-Pentane (P) A single monochloride

(B) Isopentane (Q) Only six monochlorides
(C) Neopentane (R) Only four monochlorides
(D) Cyclopentane (S) Only two dichlorides
(T) Only three trichlorides

1.B 2.D 3.A 4.A 5.C 6.C 7.B 8.A 9.B 10.C
11.B 12.B 13.B 14.B 15.B 16.A 17.D 18.A 19.B 20.B
21.D 22.B 23.A 24.B 25.C 26.B 27.A 28.A 29.B 30.A
31.D 32.C 33.A 34.C 35.B 36.C 37.A 38.D 39.A 40.C
41.B 42.B 43.B 44.B 45.C 46.C 47.A 48.D 49.A 50.C 51.B
52.AB 53.ABC 54.BC 55.AD 56.ACD
57.A 58.D 59.D 60.A 61.B 62.B 63.B 64.A 65.A 66.A
67.B 68.D 69. A-T,B-Q,C-P,D-T 70.A-R,B-Q,C-PST,D-P

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