CHAPTER 16 - HYDROCARBONS

Single Correct Type

1. Y 
BH3 /THF
H O /OH
2 2
CH3  CH2  CH2  C  CH 
H2O
H2SO4 HgSO4
 X. Where X & Y are
(A) Positional isomers (B) Functional isomers
(C) Metamers (D) Tautomers

Pd/BaSO4
X

2. CH3 C C CH3 + H2
Na/Liq. NH3
Y

Where x and y are

(A) Geometrical isomers (B) Positional isomers
(C) Functional isomers (D) Chain isomers

3. OsO4
?
(CH3)3CO2H/OH-

(A) CH 3 CHO (B) Racemic mixture of 2,3-

butanediol
(C) cis-2,3-epoxybutane (D) meso-2,3-butanediol

4. The major product formed when propene is treated with

HCl in the presence of peroxide is
(A) 2-Chloropropane (B) 1-Chloropropane
(C) Chloromethane (D) Butane

1
5. The major product in the following reaction is
CH3 3 C  CH  CH2  HCl  products

(A) (CH ) C CH CH3

(B) CH3 3 C  CH2  CH2  Cl
3 3

Cl
Cl

(C)CH3 C CH(CH3)2 (D)  CH3 3 C  CH2  CH3

CH3

6. With Bayer's reagent, Ethene and Ethyne form respectively

(A) Ethyl alcohol and oxalic acid
(B) Ethylene glycol and Oxalic acid
(C) Oxalic acid and ethylene glycol
(D) Formic acid and acetic acid

7. The compounds having degree of unsaturation = 4, are

(i) (ii)

(iii) (iv)

(A) (i), (iii) (B) (i), (iv)

(C) (iii), (iv) (D) (i), (iii), (iv)

2
8.
The probable structure of (X) is [ O * means O18 ]

(A) (B)

(C) (D)

9. Dehydration of 1-butanol gives 2-butene as a major

product, by which of the following intermediate the
compound 2-butene obtained
+ CH2
CH2 +
(A) H3C (B) H3C C

CH3
CH3

+ CH3 +
(C) H3C CH (D) H3C CH2

10. Acid catalyzed hydration of alkenes except ethene leads to

the formation of
(A)mixture of secondary and tertiary alcohols
(B)mixture of primary and secondary alcohols
(C)secondary or tertiary alcohols
(D) primary alcohols

3
 Multiple Correct Type
11. Which among the following is not true?
(A) Moist ethylene can be dried by passing it through
concentrated H2SO4.
(B) Decolorization of Baeyer’s reagent is sure test of
alkenes.
(C) Propene with diborane forms an additive product,
which on reaction with H2O2 forms propanol.
(D) Lewisite is formed by the reaction of acetylene and
arsenic trichloride.

12. Which of the following alkenes on reaction with dil. H2SO 4

will give
OH

As major product?

(A) (B)

(C) (D)

13. The ozonolysis product of is

(A) (B)
(C) Methyl glyoxal (D) Dimethyl glyoxal
4
14. The correct statement

regarding (A) & (B)

(A) Compound (A) is

(B) Compound (B) shows geometrical isomerism

(C) Compound (A) is optically active
(D) Compound (A) & (B) are stereoisomers

15. Which of the following has at least one ‘sp’ hybridised ‘C’
but does not contain triple bond?
(A) Acetonitrile (B) Triplet carbene
(C) Benzyne (D) Allene

16. Which of the following reaction(s) can be used for the

given reduction
H3C CH3
O
H3C CH3

(A) Clemmensen reaction (B) Wolf-Kishner reaction

(C) Wurtz reaction (D) HI and red phosphorus at
2000C

17. For the reaction:

–
CH3CH2–O
CH3 CH2 CH CH3 CH3CH2OH
CH3 CH2 CH CH2 + CH3 CH CH CH3
F (Major) (Minor)

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 Which of the following is/are correct?
(A) The reaction is E1 elimination
(B) The reaction is E2 is elimination
(C) Transition state has carbanion like character
(D) Transition state has carbocation like character

18. Which of the following products will be obtained if sample

CH3
CH3
of undergoes oxidative ozonolysis?
O O
|| || COOH
(A) CH3  C  C  CH3 (B) |
COOH
O
||
(C)CH3COOH (D) CH 3  C  COOH

19. Compound (X) C H O

4 8
decolorizes Baeyer’s reagent. It
undergoes hydrolysis in dil H SO
2 4
to give (Y) and (Z) where
both Y and Z give positive iodoform test while only ‘Y’
responds to Tollens test but (Z) doesn’t. Choose the correct
statements of the following:
OH/ 
(A) Y  CH  CH  CH  CHO
3
PCC/CH Cl
(B) Z 
2 2 Y

Br
Br /CCl |
(C) X 
2 4  BrCH  CH  O  CH CH
2 2 3
O /H O/z
(D) X 
3 2 2 Y  other product

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20. Which order/s are correct regarding boiling point

CH3 CH3 CH3 H CH3 Cl CH3 H

(A) C C > C C (B) C C > C C
H H H CH3 H H Cl
H
Cl Cl CH3 CH3
Cl Cl

(C) > (D) >

Cl Cl

Integer Type
21. The number of monochloro derivatives that the compound
'D' can give
3 H O,H Ca dry Zn Hg,HCl
CH 3CN 
 A 
 B  C 
D
distillation

O
H

22. H
+

P
ro
duc
t

Total number of possible products are (no stereoisomer)

23. Mass of gas (in gram) produced when one mole of CH3MgBr
is treated with 0.25 mole ethyl alcohol.
24. Find the number of  bond in the final product of following
reaction.
CH3

H C Cl

NaI
Acetone
H C Cl

CH3

7
 H -Br
25. Me ?

What is the number of stereo isomers obtained in above

reaction?
(Neglecting the minor contributors)
26. CH 3  CH  CH 2  CH 3 
|
Cl2 /CCl 4
h
 Mono halo substitution Product(s)
CH3

total no. of possible enantiomeric pairs will form are

27. In the reaction products

If compound (II) reacts with same rate as of (I) then what is
the sum of orders of possible mechanistic elimination
routes?
28. What mass of isobutylene is obtained from 37 gm of
tertiary butyl alcohol by heating with 20% H2SO4 at 363 K
if the yield is 28.6%
29. Calculate the possible number of dehydration products
when cyclopentyl methanol is heated with Conc.H2SO4.
30. It required 0.70 gm of hydrocarbon CnH2n (A) to react
completely with 2 gm Br2. On treatment of (A) with HBr, it
yielded monobromoalkane (B). The same compound (B)
was obtained when (A) was treated with HBr in the
presence of peroxide. What is the value of n in CnH2n?

8
 SOLUTIONS
Single Correct Type
1. (B)
OH
H2SO4
CH3 CH2 CH2 C CH HgSO CH3 CH2 CH2 C CH2
4

tautomerize

O
CH3 CH2 CH2 C CH3
2-pentanone
(X)

BH3/THF
CH3 CH2 CH2 C CH CH3 CH2 CH2 CH CH
H2O2/OH-
OH

tautomerize

CH3 CH2 CH2 CH2 C H

O
Pentanal
(Y)

X is a Ketone and Y is an Aldehyde. As we know,

Aldehydes and Ketones are Functional isomers. Hence, X
and Y are Functional Isomers.

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2. (A)
H H
CH3 C C CH3 + H2 Pd
BaSO4 C C
H3C CH3
Cis–butene
(X)

Na/Liq. NH3 H CH3

CH3 C C CH3 C C
H3C H
trans–butene
(Y)

Hence, X and Y are Geometrical isomers.

3. (B)
Osmium tetroxide OsO4  is a volatile liquid that is useful
for the synthesis of 1,2 diols (or vicinal diols) from alkenes.
The reaction is very mild, and usefully leads to the
formation of syn diols. (Note: this reaction doesn't work
with alkynes).
OsO4
OH OH
HO HO

(enantiomer)

4. (A)
Anti Markovnikov`s rule is not valid for addition of HCl on
alkene. Hence, HCl will react with alkenes using an
electrophilic addition mechanism and thereby will follow
Markovnikov's rule. However, in the presence of organic

10
peroxides, Hydrogen Bromide adds by a different
mechanism.
With Hydrogen Chloride, the second half of the
propagation stage is very slow. If you do a bond enthalpy
sum, you will find that the following reaction is
endothermic.

CH3 — CH — CH2Cl  HCl  CH3 — CH2 — CH2Cl   Cl

This is due to the relatively high hydrogen-chlorine bond

strength.

Similarly in case of HI, the first step of the propagation

stage turns out to be endothermic and this slows the
reaction down. Not enough energy is released when the
weak Carbon-Iodine bond is formed.

CH3 — CH  CH2   I  CH3 — CH — CH2I

In the case of Hydrogen Bromide, both steps of the

propagation stage are exothermic and therefore addition of
HBr through radical mechanism is favoured.

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5. (C)
CH3

(H3C)C CH CH2 H H3C C CH CH3

CH3
(2o carbocation)

~CH3 shift

CH3 CH3
H3C C CH CH3
o
(3 carbocation)

Cl

CH3
H3C C CH(CH3)2
Cl

6. (B)
Baeyer's reagent is an alkaline solution of cold potassium
permanganate, which is a powerful oxidant making this a
redox reaction. Reaction with double or triple bonds
(—C  C — or — C  C—) in an organic material causes the color

to fade from purplish-pink to brown. It is a syn addition

reaction. Aldehydes and formic acid (and formic acid esters)
also give a positive test.
Bayer's
Ethene 
reagent  HO  CH2  CH2  OH
Bayer's
Ethyne 
reagent  HOOC  COOH

12
7. (C)
The degree of saturation (also known as the index of
hydrogen deficiency (IHD) or number of rings plus pie
bonds) formula is used in organic chemistry to help draw
chemical structures.
Degree of unsaturation in (i) = 1+1+1=3
Degree of unsaturation in (ii) = 1+1=2
Degree of unsaturation in (iii) = 1+1+1+1=4
Degree of unsaturation in (iv) = 2+1+1=4

8. (C)
Oxacyclopropane synthesis by peroxycarboxylic acid
requires an alkene and a peroxycarboxylic acid as well as an
appropriate solvent. The peroxycarboxylic acid has the
unique property of having an electropositive oxygen atom on
the COOH group. The reaction is initiated by the
electrophilic oxygen atom reacting with the nucleophilic
carbon-carbon double bond. The mechanism involves a
concerted reaction with a four-part, circular transition state.
The result is that the originally electropositive oxygen atom
ends up in the oxacyclopropane ring and the COOH group
becomes COH.

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 In next step i.e. acid hydrolysis, H2O will attack from
opposite side of O18 as explained below in mechanism.
H CH3 OH
H3C
+
H3O
C C H C C H
hydrolysis
H CH3 *OH
O* CH3

CH3 OH
H
H *
OH CH3
*
OH
H OH
CH3
CH3
(Fischer projection) (Saw horse projection)

9. (C)
+
CH2


H3C OH 

H H3C


+
CH3   
1,2 hydride CH2
+ Shift H3C
H3C CH
2° 1°

14
10. (C)
CH 3  CH  CH 2  H 2 O 
H 2SO 4
 H3C CH CH3
OH
2° alcohol

CH3 CH3
H3C C CH2  H 2 O  H3C
H 2SO 4
C CH3
CH3
3° alcohol

Addition follows Markownikoff’s rule.

Multiple Correct Type

11. (A, B)
Statement (A) is false: ethylene combines with H2SO4
CH2 CH3 H2O
+ 2H2SO4 CH3CHO
CH2 CH(HSO4)2

Statement (B) is false: Reducing compounds can also

decolorize Baeyer's reagent
Statement (C) is true
Statement (D) is true: Lewisite is a poisonous gas used
during wars.
CH AlCl3 CHCl
+ ClAsCl2
CH CHAsCl2
Lewsite

15
12. (A, B, C, D)

13. (B, C, D)

16
14. (A, B, C, D)

15. (B, D)
Triplet carbene:
CH2
, sp-hybridisation

Allene : CH 2  C  CH 2  sp  hybridisation

16. (A, B, D)
Wurtz reaction is not applicable for the above reduction
hence, (A, B, D) is the correct answer.

17. (B, C)
CH3 CH2 O
CH3 CH2 CH CH3 CH3 CH2 CH CH2 (E2)
Major
F
(Hoffman elimination)

*Transition state has carbanion like character.

17
18. (A, B, C, D)
CH3 CHO CH3 C =0
2 +
CHO CH3 C =0
CH3

COOH 2CH3COOH
COOH
CH3 CHO CH3 C =0
+ 2
CHO CHO
CH3

COOH CH3 - C = 0
COOH
COOH
19. (A, B, C)

H O
CH  CH  O  CH  CH
2 2 3
 x  
3 
 CH CHO  CH CH OH
3 y  3 2 z 

20. (A, B, C, D)
As magnitude of dipole moment increases, b.p. increases
i.e.
CH3 CH4 CH3 H
C C > C C
H H H CH3

18
 Integer Type
21. (2)

O
H O Ca
dry distillation
CH3CN 
3  CH3COOH 
 (CH3COO)2 Ca   CH3 C CH3
(A) (B) (C)

HCl Zn—Hg

CH3 — CH2 — CH3

(D)
Cl2
CH3 — CH2 — CH3 
h
 CH3 CH CH3 + CH3 — CH2 — CH2 — Cl
(D) Cl

Number of monochloro of D will be 2.

22. (5)

23. (4)
CH 3MgBr  C2 H 5OH  CH 4  C2 H 5OMgBr
1 mole 0.25 mole 16 gm

1 mole of will produce 16 gm of CH

C2 H5OH 4

 0.25 mole of C H OH will produce 4 gm of CH

2 5 4

19
24. (1)
CH3 CH3 CH3

H C Cl H C I CH

NaI
Acetone
 I2
H C Cl H C I CH

CH3 CH3 CH3

25. (0)

26. (2)
Cl Cl Cl
| | | *
C  C C  C C  C C  C C  C C - C C C C C
*

| | | |
C C C C - Cl

Only two products contain chiral carbon atom. Hence no.

of possible enantiomeric pairs are 2.

27. (3)
This indicates that loss of proton is not occurring is rate
determining step so mechanism may either be E1 or E1CB.

28. (8)
(CH3 )3 COH 
H2SO4
 (CH3 )2 C  CH 2
mol. wt. 74 mol. wt. 56

% yield = 28.6
 real yield = 56  37  286  8.0 gm
74 100

20
29. (3)
CH2OH CH2
H+
+
H RE


1,2-hydride shift

CH2

30. (4)
(i) (A) gives monobromoalkane (B)  (A) is alkene
C=C + Br2  C–C
(ii) (A)
1 mole Br Br

Since 2 gm Br2 reacts completely with = 0.70 g of (A)

 160 gm Br2 reacts completely with = 0.70 160 = 56 gm of
2
(A)
 Molecular weight = 56
CnH2n = 56 (since compound is alkene)
12n + 2n = 56
n=4

21