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HYDROCARBONS
P REPARED BY :
E R . V INEET L OOMBA
(B.T ECH . IIT R OORKEE )
ALP
ADVANCED LEVEL PROBLEMS

TARGET : JEE Main/Adv Class XI HYDROCARBON

60 Best JEE Main and Advanced Level Problems (IIT-JEE). Prepared by IITians.
HYDROCARBONS

m
Q.1 In the given reaction

C7H12 (A) HCl



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(A) is:

(A) (B) .c (C) (D) All of these

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Q.2 1-Methylcyclopentene can be converted into the given compound
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by the use of which of the following reagents?

(A) BD3 followed by HCOOH (B) BH3 followed HCOOD
O
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||
(C) BD3 followed by HCOOD (D) BH3 followed by D  C  O  H
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Q.3 Identify (P) in the following reaction:


H / H2O
+2    (P)
ne

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

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Q.4 The reaction of E-2-butene with CH2I2 and Zn–Cu Couple in either medium leads to formation of

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

Q.5 (E)-3-bromo-3-hexene when treated with CH3O in CH3OH gives

(A) 3-hexyne (B) 2-hexyne (C) 2,3-hexadiene (D) 2,4-hexadiene
 3

Q.12 O-xylene on ozonolysis will give

O CH 3  C  O O
CHO || ||
(A) | & CH 3  C  CHO (B) | & CH 3  C  CHO
CHO CH 3  C  O

CH 3  C  O O
CH 3  C  O CHO || CHO
(C) | & | (D) | , CH 3  C  CHO & |
CH 3  C  O CHO CH 3  C  O CHO

O O (1 eq )
s 4
Q.13   X.
H 2O / Acetone
Identify ‘X’.

m
(A) (B)

o
(C)

.c (D) Reaction will not occur

ba
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PdCl , HOH
2
Q.14    Z.
CuCl 2 , O 2

Identify Z.
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(A) (B)

(C) (D) All are correct

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CH 3 CH 3
et

| | Os O 4 (1equiv.)
Q.15 CH 3  C  C  CH 2  CH  CH 2     A ; Identify A
( Acetone / water )
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CH 3 CH 3 OH OH CH3 CH 3
| | | | | |
(A) CH 3  C  C  CH 2  CH  CH 2 (B) CH 3  C — C  CH 2  CH  CH 2
| |
OH OH
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CH 3 CH 3
| |
(C) CH 3  CH — C  CH 2  CH  CH 3 (D) Reaction will not occur
| |
OH OH

Prepared By:
Er. Vineet Loomba (IIT Roorkee)
 4

Q.16 1-Penten-4-yne reacts with bromine at – 80°C to produce:

(A) 4,4,5,5-Tetrabromopentene (B) 1,2-Dibromo-1,4-pentadiene
(C) 1,1,2,2,4,5-hexabromopentane (D) 4,5-dibromopentyne

Q.17 Compound (A) on oxidation with hot KMnO4 / OH gives two compound
O
||
CH 3  CH  COOH & CH 3  C  CH 2CH 2CH 3
|
CH 3
compound A will have structure.
(A) CH 3CH 2  C  C  CH 2CH 3 (B) CH 3  CH  CH  C  CH 2CH 2CH 3
| | | |
CH 3 CH 3 CH 3 CH 3

m
(C) CH 3CH  C  C  CH 3 (D) CH 3  CH  C  C  CH  CH 3
| | |
CH 3 CH 3 CH3

o
Q.18 Consider the following reaction
KMnO / OH  / 
(A) C6H12  4   C5H10O
In the above reaction (A) will be .c
ba
(A) CH3–CH2–CH2–CH2–CH=CH2 (B) CH 3  CH  CH 2  CH  CH 2
|
CH 3
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(C) CH 3  CH 2  CH  CH  CH 2 (D) CH 3CH 2CH 2  C  CH 2

| |
CH 3 CH 3
lo

Q.19 alcoholic KOH

 product
   

Major product is:

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

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Q.20 Number of required O2 mole for complete combustion of one mole of propane –
(A) 7 (B) 5 (C) 16 (D) 10

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vi

Q.21 How much volume of air will be needed for complete combustion of 10 lit. of ethane –
(A) 135 lit. (B) 35 lit. (C) 175 lit. (D) 205 lit.

Q.22 When n-butane is heated in the presence of AlCl3/HCl it will be converted into –
(A) Ethane (B) Propane (C) Butene (D) Isobutane

Q.23 The reacting species of alc. KOH is –

(A) OH– (B) OR+ (C) OK+ (D) RO–

Prepared By:
Er. Vineet Loomba (IIT Roorkee)
 6
Q.36 Which of the following reagents cannot be used to locate the position of triple bond in CH3–CC–CH3
2
(A) Br2 (B) O3 (C) Cu 2 (D) KMnO4

Q.37 CH3–CH2–CCH CH3CC–CH3

A and B are –
(A) alcoholic KOH and NaNH2 (B) NaNH2 and alcoholic KOH
(C) NaNH2 and Lindlar (D) Lindlar and NaNH2

3 BH / THF H O
Q.38 B    3
  A
H 2 O 2 / OH
A and B are –

(A) Both (B) Both

m
(C) (D)

o
3 BH THF
Q.39 B    CH3–CCH HgSO / H SO
 4 24  A

H 2O 2, OH

A and B are –
O
.c O
ba
|| ||
(A) CH 3CH 2 CHO, CH 3  C  CH 3 (B) CH 3  C  CH 3 CH 3CH 2 CHO

(C) CH3CH2CHO (both) (D) CH 3  C  CH 3 (both)

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||
O

2 6 B D
Q.40 CH3CH=CH2   product X
H 2O 2 / OH
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X is –
(A) CH 3  CH  CH 2 D (B) CH 3  CH  CH 2 OH
| |
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OH D

(C) CH 3  CH  CH 3 (D) none is correct

|
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OD
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Q.41 CH2=CH–CH=CH2 CCl
 3Br
 product. The major product is –
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(A) Br–CH2–CH=CH–CH2–CCl3 (B) CH 2  CH  CH  CH 2  CCl 3

|
Br

(C) CH 2  CH  CH  CH 2  Br (D) None is correct

|
CCl 3

Prepared By:
Er. Vineet Loomba (IIT Roorkee)
 7

Q.42 Mixture of one mole each of ethene and propyne on reaction with Na will form H2 gas at S.T.P. –
(A) 22.4 L (B) 11.2 L (C) 33.6 L (D) 44.8 L

Q.43 Dehydration of 2, 2, 3, 4, 4–pentamethyl–3–pentanol gave two alkenes A and B. The ozonolysis products of A and B are -
O
||
(A) A gives (CH 3 ) 3 C  C  C(CH 3 ) 3 and HCHO

O
||
B gives CH  C  CH  C( CH ) and HCHO
3 2 3 3

O
||
(B) A gives (CH 3 ) 3 C  C  C(CH 3 ) 3 and HCHO

O CH 3

m
|| |
B gives CH  C  C  C(CH ) and HCHO
3 3 3
|

o
CH3

(C)
O
||
.c
A gives (CH ) C  C  CH (CH ) and HCHO
3 3 3 2
ba
O
||
B gives (CH 3 )  CH 2  C  C(CH 3 ) 3 and CH3CH2CHO
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(D) None of these

NH Cl
Q.44  4 product
CHCH Cu Cl 2 2
Product is –
lo

(A) Cu–CC–Cu (B) CH2=CH–CCH (C) CHC–Cu (D) Cu–CC–NH4

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et

O
||
Q.45 Alkene A O 3 / H2O
  CH  C  CH 3 + CH3COOH + CH 3  C  COOH
ne

3
||
O
A can be –

C(CH 3 ) 2
vi

||
(A) (B) CH 3  C  CH  HC  CH 3
(C) Both correct (D) None is correct

Prepared By:
Er. Vineet Loomba (IIT Roorkee)
 8

Q.46 reagent R reagent R

  2  1 

R1 and R2 are –
(A) Cold alkaline KMnO4, OsO4/H2O2 (B) Cold alkaline KMnO4, HCO3H
(C) Cold alkaline KMnO4, CH3–O–O–CH3 (D) C6H5CO3H, HCO3H

CH 3
|
HC
Q.47 || alkaline KMnO
HC
   4  A, which is true about this reaction?
|
CH 3

m
(A) A is meso 2, 3–butan–di–ol formed by syn addition
(B) A is meso 2, 3–butan–di–ol formed by anti addition
(C) A is a racemic mixture of d and l, 2, 3–butan–di–ol formed by anti addition
(D) A is a racemic mixture of d and l 2,3–butan–di–ol formed by syn addition

o

Con . H SO O 3 / H 2O / Zn
Q.48 + CH3MgBr H
 3O
 A  24  B    C
A, B and C are –
A B
.c C
ba
(A)
om

(B)
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(C)
et
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(D)

A

vi

Q.49

A can be –
(A) Conc. H2SO4 (B) alcoholic KOH (C) Et3N (D) t-BuOK

Q.50 BrCH2–CH2–CH2Br reacts with Na in the presence of ether at 100 °C to produce –

(A) BrCH2–CH=CH2 (B) CH2=C=CH2 (C) (D) All of these

Prepared By:
Er. Vineet Loomba (IIT Roorkee)
 9

Q.51 Which has least heat of hydrogenation –

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

(1) Hg ( OAc ) / H O / THF

2
Q.52     2  
 A. A is –
( 2 ) NaBH 4 / NaOH / H 2O

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

Q.53 An organic compound of molecular formula C4H6, (A), forms precipitates with ammoniacal silver nitrate and ammoniacal
cuprous chloride. ‘A’ has an isomer ‘B’, one mol of which reacts with one mol of Br2 to form 1, 4-dibromo-2-butene. Another
isomer of A is ‘C’, one mole of C reacts with only 1 mol. of Br2 to give vicinal dibromide. A, B & C are

(A) CH3–CH2–CCH and CH2=CH–CH=CH2 ;

m
(B) CH3–CC–CH3 and CH3–CH=C=CH2 ; CH3–CC–CH3

CH 2  CH

o
(C) C=CH2 and | | | ; CH2 = CH–CH=CH2
CH 2  CH

(D) CH3–CC–CH3 and

.c ; CH2 = CH–CH = CH2
ba
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x
Q.54 CH3–CH=CH–CH3   product is Y (non–resolvable) then X can be –
om

cis
(A) Br2 water (B) HCO3H
(C) Cold alkaline KMnO4 (D) all of the above

Q.55 Electrophilic addition reaction is not shown by

(A) CH 2  C  CH 3 and Br2 (B) CHCH2 and HO–Cl
lo

|
CH 3
et

(C) CH3–CCH and CH3MgBr (D) CH2=CH2and dil. H2SO4 solution

Q.56 A mixture of CH4, C2H4 and C2H2 gaseous are passed through a Wolf bottle containing ammonical cuprous chloride. The gas
coming out is
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(A) Methane (B) Acetylene

(C) Mixture of methane and ethylene (D) original mixture

Q.57 In the presence of strong bases, triple bonds will migrate within carbon skeletons by the
(A) removal of protons (B) addition of protons
vi

(C) removal and readdition of protons (D) addition and removal of protons.
CHCOOH
Q.58 CH2=CH–CH=CH2 + || 
 product X by reaction R. X and R are
CHCOOH

(A) Diels Alder (B) Friedel-Crafts

Prepared By:
Er. Vineet Loomba (IIT Roorkee)
 10

(C) Diels Alder (D) Friedel-Crafts

Q.59 For the ionic reaction of hydrochloric acid with the following alkenes, predict the correct sequence of reactivity as measured
by reaction rates:
(I) ClCH=CH2 (II) (CH3)2.C=CH2 (III) OHC.CH=CH2 (IV) (NC)2C=C(CN)2
(A) IV > I > III > II (B) I > IV > II > III (C) III > II > IV > I (D) II > I > III > IV

Q.60 The addition of bromine to 2-cyclohexenyl benzoate in 1,2-dichloroethane produces ____ dibromo derivatives:
(A) 2 (B) 3 (C) 4 (D) 6

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et
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ANSWER KEY (vineetloomba.com)

Q.1 D Q.2 B Q.3 A Q.4 B Q.5 A Q.6 D Q.7 C

Q.8 C Q.9 A Q.10 C Q.11 D Q.12 A Q.13 B Q.14 A

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Q.15 B Q.16 D Q.17 B Q.18 D Q.19 A Q.20 B Q.21 C

Q.22 D Q.23 A Q.24 A Q.25 B Q.26 A Q.27 C Q.28 B
Q.29 B Q.30 C Q.31 A Q.32 D Q.33 A Q.34 B Q.35 B
Q.36 A Q.37 A Q.38 D Q.39 B Q.40 B Q.41 A Q.42 B
Q.43 B Q.44 B Q.45 C Q.46 B Q.47 A Q.48 A Q.49 A
Q.50 C Q.51 C Q.52 C Q.53 A Q.54 C Q.55 C Q.56 C
Q.57 C Q.58 A Q.59 D Q.60 A

Prepared By:
Er. Vineet Loomba (IIT Roorkee)