HYDROCARBONS

MULTIPLE CHOICE QUESTIONS

1. 6-Methyl-1, 5-heptadiene on treatment with H2SO4/H2O
gives
+
(a) C
H—
3 C
—(C
H)
23—C
H=C
H2 (b) H
3C
C
H H
3C O
SOH
3
3

(c) H3C +
(d) HC
3
H3C HC
3 OH

Sol. (d)
H
+ +
CH2 = CH — CH2 — CH2 — CH = C — CH3 CH2 = CH — CH2 — CH2 — CH2 — CH2 — C — CH3

CH3 CH3
OH
+

H2O
CH3 -H
+ CH3
CH3 CH3

Me Me
H
2.
H
Me H

Hydrogenation of the above compound in the presence of

poisoned Pd catalyst gives
(a) an optically active compound.
(b) an optically inactive compound.
(c) a racemic mixture.
(d) a diastereomeric mixture.

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Sol. (b)
Product contains no chiral centre.

Br
3. , when treated with two equivalents of sodium in dry
Cl
ether gives:
Br Cl
(a) (b)
(c) (d)
Sol. (d)
Br
2Na
.
Cl
.

4. Addition of HOCl to ethyne gives:

(a) ethyl chloride (b) vinyl chloride
(c) dichloroacetaldehyde (d) ethylidene chloride
Sol. (c)
OH Cl Cl
CHCH + HOCl  CH=CH 
HOCl
CH–CH 
–H2O
CH–CHO
OH Cl OH Cl Cl

CHO
O3/H2O, Zn
5. [A] + 2HCHO. In this reaction (A) and (B) are:
CHO
HOCl
[B]

(a) CH2=C=CHCH3, CH2=CHCHCH2

OH Cl
Cl
(b) CH2=CHCH=CH2, CH3CHCHCH3
OH

2
 OH
(c) CH3CCCH3, CH3C=CCH3
OH
(d) none of these
Sol. (d)

Cl
6. alc.
KOH
(A) NBS
(B)
alc.
KOH
(C) NBS
(D)
alc.
KOH
(E)

The product E is:

Br

(a) (b)
Br
(c) (d)
Sol. (c)
Br
Cl
alc. NBS alc. NBS alc.
KOH KOH KOH
(A) (B) (C) Br (D) (E)

7. The final product (Z) formed in the following reaction

sequence is
CH3
NBS 1. CH C  N
 (X)   (Y)  3 
Mg / ether


CCl 4 2. H 2 O / H
CH3
(Z)
O CH3
H3C CH3
(a) C CH3 (b) OH
H3C
COCH3
CH3
(c) CH3
(d) no reaction

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Sol. (a)
CH3
NBS Mg – + CH3 – C  N
Br MgBr H+
C = NH
CCl4 either

H2O/H+ CH3

C=O

8. Structural formula for lewsite is

CHCl CHCl
(a) || (b) ||
CHAsCl 3 CHAsCl
CHCl CH 2
(c) || (d) ||
CHAsCl 2 CHAsCl 2

Sol. (c)
Lewsite is made by the following reaction.
CH CH + AsCl3ClCH=CHAsCl2. It is a war gas made by
(Lewsite)

Germans.
Its antidote is BAL. (British Anti lewsite) CH2–CH–CH2
SH SH OH

9. Reaction of one molecule of HBr with one molecule of 1,

3-butadiene at 40ºC gives predominantly
(a) 3–bromo–1–butene under kinetically controlled
conditions.
(b) 1–bromo–2–butene under thermodynamically
controlled conditions.
(c) 3–bromo–1–butene under thermodynamically controlled
conditions.

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 (d) 1–bromo–2–butene under kinetically controlled
conditions.
Sol. (b)
CH2 = CH – CH = CH2 + HBr 40ºC
 CH 2  CH  CH  CH 3 [1, 4
|
Br
adduct].
Thermodynamically controlled

10. The chemical reactions of an unsaturated compound (M) of

molecular formula C8H14 are given below. Determine the
possible structural formula of (M).

(i) O3
C8H14O2(N)
(ii) Zn | H2O
C8H14(M)
H2/Ni Cl2/h
C8H16 (O) C8H15Cl(P) (only one monochloro product)

(a) (b)

(c) (d)

Sol. (c)
Compound (M) upon ozonolysis gives (N) which has same
number of carbon as that of (M). That means it is a cyclic
compound. On hydrogenation followed by chlorination it
gives only one product. Hence the product is cyclooctene.

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 CHO

11. An alkene (A) 


Ozonolysis
A is
CHO

(a) (b)

(c) (d)

Sol. (c)
6 54 CHO
4
3 O3
5 3
1
2 6 2
1
CHO

12. Ozonolysis of Agathene dicarboxylic acid gives

H3C COOH
CHO
, H2CO and |
O COOH
H3 C
CH2CH2COCH3

Structure of Agathene dicarboxylic acid should be

H3C COOH H3C COOH

(a) CH2
(b) CH2
H3C COOH H3C COOH

H3C COOH H3C COOH

(c) CH2
(d)
CH2
H3C COOH H3C COOH
CH3 CH2CH3

Sol. (c)

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13. (X ) Br
2
( Y ) 3 
NaNH 2
C  C – CH3 , then (X) will be
CH 3I

CH2 – CH3

(a) (b) CH = CH2

C  CH
(c) CH2 – C – CH2 (d)
H
Sol. (b)
Br
Br2 2NaNH2
CH = CH2 CH – CH2 C  CH
(X)
Br NaNH2
CH3 – I –
C  C – CH3 C  CNa+

14. 1 2 3

Then which of the following is not used in; 1, 2 and 3

positions?
(a) O3/H2O (b) LiAlH4
(c) H2SO4 (d) HI / red P
Sol. (d)
O3 LiAIH4
O OH
H2SO4

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15. Predict the product formed in the reaction
(i) B2H6\THF (excess)
H2C CH2 
(ii) H2O2\OH

OH
(a) HOCH2 CH2OH (b) CH2OH
CH3
OH OH OH
(c) H2C (d)
CH3 H3C CH3

Sol. (a)
Product according to anti markonikoff rule.

16. The heat of hydrogenation of 1–hexene is –126 kJ mol–1.

When a second double bond is introduced in the molecule,
the heat of hydrogenation of the resulting compound is
–230 kJ mol–1. The resulting compound (diene) is
(a) 1, 3–Hexadiene (b) 1, 4–Hexadiene
(c) 1, 5–Hexadiene (d) cannot predict from the
given information
Sol. (a)
Since the H value expected for two double bonds = –126
 2 = –252 kJ.
While the observed is only 230 kJ
 There is conjugation.

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17. End product of the following sequence of reaction is:
NBS Mg/ether CH3CN
(A) (B) H3O+
(C)

COCH3
COCH3
(a) (b)
CN COOH

(c) (d)

Sol. (b)
NBS Mg CH3CN H3O+
dry ether

Br MgBr C=NMgBr C=O

CH3 CH3

18. Identify the products (A), (B) and (C) formed in the
following sequence of reactions
(i) BH3–THF
(A)
(ii) NaOH–H2O2

(i) Hg(OAc)2, H2O

C6H5–CH2CH=CH2 (B)
(ii) NaBH4

H+, H2O
(C)

(a) C6H5CH2CH2–CH2OH, C6H5–CH–CH2–CH3, C6H5–CH2–CH–CH3

(A) OH (B) (C) OH

(b) C6H5CHCH2–CH3, C6H5–CH2–CH2–CH2OH, C6H5–CH2–CH–CH3

OH (A) (B) (C) OH

(c)
C6H5–CH2–CH–CH3, C6H5CHCH2–CH3, C6H5–CH2–CH2–CH2OH
(A) OH OH (B) (C)

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 (d) C6H5CH2CH2–CH2OH, C6H5–CH2–CH–CH3, C6H5–CH–CH2–CH3
(A) (B) OH OH (C)

Sol. (d)

19. When isobutane is monochlorinated in the presence of

ultraviolet light, the product obtained in higher yield is
(a) nbutyl chloride (b) isobutyl chloride
(c) secbutyl chloride (d) tertbutyl chloride
Sol. (b)
Cl
Cl2/h
CH3CHCH3 CH3CHCH2Cl + CH3CCH3
CH3 CH3 CH3
 
 isobutyl chloride
= no. of 1 H  reactivity of 1 H =91
tert butyl chloride no. of 3 H  reactivity of 3 H 1 5

20. The following synthesis is best carried out by

I
CH = CH2 CH = CH2

Cl I

(a) Cl
 2
 ICl
 / C
HCOOH
  ICl
3
 / C
HCOOH Zn dust , CH COOH
        
3 3

(1) (2) (3) (4)

 Cl / Fe ICl / ZnCl (excess) NaOH, 
(b) HOCl
 / H
 2   2      
(1) (2) (3) (4)
 Cl / Fe ICl / ZnCl (excess) Zn dust , CH COOH
(c) HOBr
 / H
 2  2     3
(1) (2) (3) (4)
Br / CH COOH Cl / Fe ICl / CH COOH (excess) NaNH
(d) 2   3 
 2   3         2
(1) (2) (3) (4)

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Sol. (c)
OH OH

CH = CH2 CH – CH2Br CH
HOBr/H+ Cl2/Fe
(1) (2)
Cl CH2

Cl Br
I I
(3)
CH = CH2 CH ICl/ZnCl2
Zn/CH3COOH
(4)
CH2 Br (excess)
Cl I Cl I

21. Which of the following will produce C2H6 on reaction with

C2H5MgBr in significant amount?
(a) (Toluene)C6H5CH3 (b) (Benzyne)
CO

(c) (Phthalimide) CO
NH
(d) (Cyclopropene)
Sol. (c)
Hatom attached to nitrogen is acidic in nature.

22. 1-methyl cyclopentene can be converted into the following

compound
D

CH3
OD

by which of these reagents?

(a) Hg (OAc)2/D2O followed by NaBD4
(b) Hg(OAc)2/H2O followed by NaBH4
(c) Hg(OAc)2/D2O followed by NaBH4
(d) Hg(OCOCD3)2/H2O followed by NaBH4

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Sol. (a)
Hg(OAc) D
Hg(OAc)2
CH3 NaBD4
CH3
CH3 OD OD
+ D2O

INTEGER TYPE QUESTIONS


( CH 3 )3 C O K  Cold alk .
23. (CH3)3CBr     (A) 

NBS
(B)  (C).
 
KMnO4

The total number of stereoisomers possible for the

compound (C) is
Sol. (2)

CH2Br CH2Br
(CH3)3COK+ NBS cold alk. *
(CH3)3CBr (CH3)2C=CH2 CH3C=CH2 CH3 C CH2
KMnO4
(A) (B) OH OH
(C)

Compound (C) has one chiral Catom. Therefore, it has

two stereoisomers.

24. An organic compound (A) contains only C, H and O atoms.

On reaction with excess of CH3MgI, one mole of (A) gives
a gas (X) whose volume under STP conditions was found
to be 67.2 litre. The number of hydroxyl groups in the
compound (A) are
Sol. (3)
67.2
= mole of gas(X) evolved = 3 mole of gas(X)
22.4

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 The number of active Hatom present in a molecule is
equal to the number of moles of gas obtained i.e. no. of 
OH groups in compound (A) = 3.

25. The number of possible enantiomeric pairs that can be

produced during monochlorination of 2methylbutane is
Sol. (2)
H Cl chiral
Cl2
CH3–CH–CH2–CH3 h Cl–CH2–C–C2H5 and CH3–CH–C–CH3
CH3 CH3 chiral CH3 H

Thus, 2 pair of enantiomers are formed.

26. Isopentane can form four monobromo isomeric derivatives.

How many of them are optically active?
Sol. (2)
CH3 CH3 CH3
*
CH3–CH–CH2–CH3 
Br2
CH3–CH–CH–CH3 + CH2–CH–CH2–CH3
*
Br Br


( CH 3 )3 C O K  Cold alk .
27. (CH3)3CBr     (A) 

NBS
(B)  (C).
 
KMnO4

The total number of stereoisomers possible for the

compound (C) is:
Sol. (2)

CH2Br CH2Br
(CH3)3COK+ NBS cold alk. *
(CH3)3CBr (CH3)2C=CH2 CH3C=CH2 CH3 C CH2
KMnO4
(A) (B) OH OH
(C)

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 Compound (C) has one chiral Catom. Therefore, it has
two stereoisomers.

28. The number of possible enantiomeric pairs that can be

produced during monochlorination of 2methyl butane is
Sol. (2)

CH3CHCH2CH3 gives two pairs of enantiomers CH2ClCHCH2CH3
CH3 CH3

and CH3CHCHClCH3.
CH3

29. The treatment of CH3OH with CH3MgI release 1.04 mL of

a gas at STP. The mass of CH3OH added is
Sol. (1.49 mg)
ngas= 1.04 = n CH OH 3
22400
1.04
WCH3OH  × 32 g ~ 1.49 mg
22400

30. The enthalpy of combustion of cyclohexane, cyclohexene

and H2 are respectively –3920,
–3800 and –241 kJ mol–1. The heat of hydrogenation of
cyclohexene is
Sol. (–121 kJ mol–1)
C6H12 + 9O2 6CO2 + 6H2O …(i)
2C6H12 + 17O2 12CO2 + 10H2O …(ii)
H2 + ½O2 H2O …(iii)

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To arrive this equation
C6H10 + H2 C6O12 …(iv)
Adding equation (ii) and (iii) and then subtracting (i), we
get equation (iv)
(–3800 –241) – (–3920) kJ mol–1
–4041 + 3920 = –121 kJ mol–1

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