Download as pdf or txt
Download as pdf or txt
You are on page 1of 40

Chapter 15

Hydrocarbons

Solutions

SECTION - A
Objective Type Questions

1. The difference in potential energy between eclipsed and staggered form of ethane is
(1) Zero kJ/mol (2) 12.5 kJ/mol
(3) 22 kJ/mol (4) 44 kJ/mol
Sol. Answer (2)
In alkanes, C–C single bond rotation is hindered by a small energy barrier of 1-20 kJ mol–1 due to torsional
strain.

2. Eclipsed form of ethane has higher energy due to


(1) Torsional strain (2) Dipole moment
(3) van der Waal’s strain (4) Hydrogen bonding
Sol. Answer (1)
Eclipsed form of ethane has maximum torsional strain and hence, highest energy.

3. The angle strain in cyclopentane is


(1) 72° (2) 1°28
(3) 44 (4) 108°
Sol. Answer (3)

sp3
(Hence, 109° 28)

10928   109.5  
Angle strain = 
2 2

⎛ 360 ⎞
Where,   180  ⎜ ⎟
⎝ 5 ⎠

3 3
Angle strain = 0.75° =  1   60  45
4 4

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
34 Hydrocarbons Solutions of Assignment

4. Which one is not aromatic compound?


(1) (2)


(3) (4)

Sol. Answer (4)


is antiaromatic compound (4e–)

5. The incorrect match is

(1) – Antiaromatic

(2) – Aromatic
N
H

(3) – Non-aromatic

(4) – Aromatic

Sol. Answer (2)

is antiaromatic compound (8e–)


N
H

6. Which one of the following statements is not correct for sigma- and pi-bonds formed between two carbon
atoms?
(1) Sigma-bond is stronger than a pi-bond
(2) Bond energies of sigma- and pi-bonds are of the order of 264 kJ/mol and 347 kJ/mol, respectively
(3) Free rotation of atoms about a sigma-bond is allowed but not in case of a pi-bond
(4) Sigma-bond determines the direction between carbon atoms but a pi-bond has no primary effect in this
regard
Sol. Answer (2)
Sigma-bond is stronger than pi-bond.
Bond energy (sigma) > Bond energy (pi)
Hence, option (2) is incorrect.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 35
CH3

7. A + NaOH CH3 – C – CH2 – CH3 ;
(CaO)
(Soda lime) H
The possible compound "A" is

CH3 CH3
(1) CH3 – C – CH2COONa (2) CH3 – C – CH2 – CH2 – COONa
H H

CH3
(3) CH3 – CH2 – CH – CH2 – COONa (4) Both (2) & (3)

Sol. Answer (4)


Soda lime, 
R – COONa R–H
NaOH + CaO

CH3 CH3
Soda lime
CH3 – C – CH2 – CH2 – COONa CH3 – C – CH2 – CH3
H H
CH3 CH3
Soda lime
CH3 – CH2 – CH – CH2 – COONa CH3 – CH2 – C – CH3
H
CH3 CH3
Soda lime
CH3 – C – CH2COONa CH3 – C – CH3
H H
8. On electrolysis of sodium succinate the alkene obtained is ______ and nature of solution after electrolysis is
______

CH2 CH2 CH CH3


(1) and acidic (2) and basic (3) and acidic (4) and basic
CH2 CH2 CH CH3
Sol. Answer (2)

CH2COONa 2H2O CH2


+ 2CO2 + 2NaOH + H2
CH2COONa Electrolysis CH2 Cathode
(Sodium Succinate) ethene
Anode

Due to NaOH formation, solution becomes basic.

9. Which one is not prepared by Wurtz reaction?


(1) C2H6 (2) n-C4H10

CH3 CH3
(3) CH4 (4) CH 3 – CH – CH – CH 3

Sol. Answer (3)


Dry ether
R  Cl  2Na  Cl  R   R  R  2NaCl
Smallest molecular weight alkane prepared by wurtz reaction is C2H6 (ethane).

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
36 Hydrocarbons Solutions of Assignment

CH3 CH3
| |
10. In CH3–C–OH, CH3–CH–OH, CH3–CH2–CH2OH
|
CH3
(I) (II) (III)
The ease of rate of dehydration is
(1) (I) > (II) > (III) (2) (II) > (I) > (III) (3) (III) > (II) > (I) (4) (I) > (III) > (II)
Sol. Answer (1)
More the stability of carbocation formed, easier will be the dehydration of Alcohol.
Stability of carbocation : 3° > 2° > 1°

CH2CH3

11. can be prepared by

(1) Wurtz reaction (2) Fittig reaction (3) Wurtz fittig reaction (4) Frankland reaction
Sol. Answer (3)
Wurtz Fittig reaction

Dry ether
Cl + 2Na + Cl – CH2 – CH3 CH2 – CH3 + 2NaCl

Na CH3Br
12. Mg2C3 + H2O A B C ;
The incorrect statement for C is
(1) Compound "C" is CH3 – C  C – CH3 (2) "C" gives positive Tollens test
(3) In compound "C" all four C are linearly present (4) Compound "C" on ozonolysis gives diketone
Sol. Answer (2)
Na
Mg2C3 + H2O CH3 – C  CH CH3 – C  C Na
Propyne B
A
CH3Br
O O
(i) O3 + CHCl3
CH3 – C – C – CH3 (ii) Zn + H2O
CH3 – C  C – CH3
diketone But-2-yne
C

13. In the following compounds, the decreasing order of B.P. is


(I) CH 3 – CH 2 – CH 2 – CH 2 – CH 2 – CH3
CH3
(II) CH3 – CH – CH2 – CH2 – CH3
CH3
(III) CH3 – C – CH2 – CH3
CH3
(1) (I) > (II) > (III) (2) (I) > (III) > (II) (3) (II) > (III) > (I) (4) (III) > (II) > (I)
Sol. Answer (1)
As the branching increases, boiling point of hexane decreases.
Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 37
CH3
Cl2
14. CH3 – CH – CH2 – CH3 UV light (A) ; The compound "A" is
Major
CH3 CH3
(1) CH3 – CH – CH – CH3 (2) CH3 – C – CH2 – CH3
Cl Cl
CH3 CH2Cl
(3) CH3 – CH – CH2 – CH2Cl (4) CH3 – C – CH2 – CH3
H
Sol. Answer (1)

CH3
Cl2
CH3 – CH – CH2 – CH3 UV light

CH3 CH3 CH3 CH2Cl


CH3 – CH – CH2 – Cl + CH3 – CH – CH – CH3 + CH3 – C – CH2 – CH3 + CH3 – CH – CH2CH3
Cl Cl

15. Octane number is zero for


(1) n-hexane (2) n-heptane (3) Iso-octane (4) Gasoline
Sol. Answer (2)
By definition, Octane number (RON) is zero for n-heptane.
Petrol with same knocking characteristics (and not, proportions) as a mixture of 90% iso-octane and 10%
n-heptane would have an octane rating of 90.

16. n-hexane on heating in presence of Cr2O3 gives


(1) Cyclohexene (2) Benzene (3) Cyclohexyne (4) None of these
Sol. Answer (2)

Cr2O3
CH3 – (CH2)4 – CH3 + 3H2

n-hexane
Benzene

17. The incorrect match is


Hydrocarbons Octane numbers
(1) 1-propanol – 118
(2) 2,5-dimethylfuran – 101
(3) Ethanol – 109
(4) Isooctane – 0
Sol. Answer (4)
Octane number is 100 for isooctane by definition.

18. A mixture of ethyl iodide and n-propyl iodide is subjected to Wurtz reaction. The hydrocarbon which will not
be formed is
(1) Butane (2) Propane (3) Pentane (4) Hexane

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
38 Hydrocarbons Solutions of Assignment

Sol. Answer (2)


Dry ether
C2H5I  2Na  I  C2H5   C2H5  C2H5  2NaI
Butane

Dry ether
C3H7  I  2Na  I  C3H7 
 C3H7  C3H7  2NaI
Hexane

Dry ether
C3H7  I  2Na  I  C2H5 
 C3H7  C2H5  2NaI
Pentane

19. Indicate the expected structure of the organic product when ethyl magnesium bromide is treated with heavy
water (D2O)
(1) C2H5–C2H5 (2) C2H5OD (3) Sodium benzoate (4) C2H5D
Sol. Answer (4)

C2H5  Mg  Br  D2O  C2H5  D  Mg(OD)Br

20. In iodination, for preparation of iodomethane compound used is


(1) HIO3 (2) HgO (3) Both (1) & (2) (4) HI
Sol. Answer (3)

CH4  I2  CH3  I  HI
Iodomethane

The purpose of HIO3 and HgO is to oxidise HI into I2.

21. In chlorination, the relative rate of abstraction of H in 3°, 2° and 1° H atom respectively is
(1) 5 : 3.8 : 2 (2) 5 : 3.8 : 1 (3) 1600 : 82 : 1 (4) 1600 : 5 : 82
Sol. Answer (2)
In chlorination 1 2 3
Relative rate 1 : 3.8 : 5

OH
H3PO4
22. In "A" ; Compound "A" is
 Major
CH2 O

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

Sol. Answer (2)


OH
H3PO4
+ H2O

(Major)
Major alkene is formed by Saytzeff rule.

23. When butyne-2 is reacted with Na in liquid ammonia in presence of C2H5OH then the major product formed
is
(1) Cis-butene-2 (2) Trans-butene-2 (3) Butene-1 (4) No reaction
Sol. Answer (2)
Na in liq. NH3 CH3 H
CH3 – C  C – CH3 C=C
butyne-2 H CH3
Trans-butene-2
(Major)

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 39

(i) (CH3COO)2 Hg Conc. H SO


24. CH3  C  CH  
 (A) 

2 4
 (B)
(ii) NaBH4 /OH

The product (B) is


(1) Mesitylene (2) Toluene
(3) 1,3,5-trimethyl benzene (4) Both (1) & (3)
Sol. Answer (4)
CH3
(i) (CH3COO)2Hg Conc. H2SO4
CH3 – C  CH (ii) NaBH /OH– CH3COCH3 
4
A CH3 CH3
B
Mesitylene
or
1,3,5-trimethyl benzene

Na/liq. NH3
25. CH3 – C  C – CH3 A ;
Pd/CaCO3
B ;
(CH3COO)2Pb

The minimum heat of hydrogenation is in


(1) (A) (2) (B) (3) Both have equal (4) Cannot predict
Sol. Answer (1)

Na/liq. NH3 CH3 H


CH3 – C  C – CH3 C=C
H CH3
(trans) (More stable)
A
CH3 CH3
Pd/CaCO3 C=C
(CH3COO)2Pb H H
(cis) (less stable)
B
More the stability of alkene, lesser will be its heat of hydrogenation.

26. In which of the following reactions, Markownikov’s rule is not observed ?

(1) CH3CH = CH2 + HCl  Organic Peroxide


(2) CH3CH = CH2 + HBr 

(3) CH3CH = CH2 + HBr  (4) CH3CH = CH2 + H2SO4 


Sol. Answer (2)

CH3  CH  CH2  HBr 


organic peroxide
 CH3  CH2  CH2  Br

Above reaction take place according to Anti-markownikov's rule.

27. CH3 – CH2 – CH3 and CH3 – C  CH can be distinguished by


(1) Baeyer's reagent (2) Tollen's Test (3) Br2/CCl4 (4) All of these
Sol. Answer (4)
All of these react with CH3 – C  CH.
None of these react with CH3 – CH2 – CH3.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
40 Hydrocarbons Solutions of Assignment

28. C6H5CH2CH2CH3 is when oxidised in the presence of alk. KMnO4, the product obtained is
(1) C6H5CHO (2) C6H5COOH (3) C6H5CH2CH2CHO (4) None of these
Sol. Answer (2)

C6H5CH2CH2CH3 
alk. KMnO 4
[O]
 C6H5  COOH
benzoic acid

29. In an attempt to prepare propane by Wurtz reaction, 1 mole of methyl bromide and 1 mole of ethyl bromide are
treated with sodium. Assuming equal probability for all possible reactions, how many grams of propane will be
obtained?

44
(1) 44 g (2) 22 g (3) 33 g (4) g
3
Sol. Answer (4)

CH3  Br  2Na  Br  C2H5  CH3  C2H5  2NaBr


1 1
mol mol (propane)
3 3

(because equal probability)


CH3 – Br + 2Na + Br – CH3  CH3 – CH3 + 2NaBr
C2H5 – Br + 2Na + Br – C2H5  C2H5 – C2H5 + 2NaBr

1 ⎛ 1 ⎞ 44
Mol of propane =  w (propane) = ⎜ 44  ⎟  g
3 ⎝ 3⎠ 3

30. Addition of HBr to 2-methyl-1-propene in the presence of hydrogen-peroxide produces


(1) 1-Bromobutane (2) 2-Bromopropane
(3) 2-Bromo-2-methylpropane (4) 1-Bromo-2-methylpropane
Sol. Answer (3)

CH3 CH3
H2O2
CH3 – C = CH2 + HBr CH3 – C – CH3
2-methyl-1-propene
Br
2-bromo-2-methylpropane

Above reaction take place according to markonikov's rule.

K2Cr2O7
31. C6H5CH3
H2SO4
Y . Here Y is

(1) Benzaldehyde (2) Toluene (3) Benzoic acid (4) Ethylbenzene


Sol. Answer (3)
K2Cr 2O7
C 6H 5 – CH 3 C6H5 – COOH
H2SO4
Benzoic acid

32. C 6H6   
Oxidation
 X . Here, X is
V2O 5 / 

(1) Maleic anhydride (2) Acetic acid (3) Propanoic acid (4) Succinic acid

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 41
Sol. Answer (1)
O
V2O5,  CH – C
O
oxidation CH – C
(C6H6)
O
(Maleic anhydride)

(1) B2H6
33. "A" . "A" is
(2) H2O2/OH (Major)
OH
OH
(1) (2) OH (3) (4)
OH
Sol. Answer (1)

(i) B2H6
(ii) H2O2/OH–
OH
(Major)
In HBO reaction, addition of H2O take place according to Antimarkonikov's rule.

CH3
C KMnO4 + H2SO4 NaOH
34. A B ; Compound B is
CH CaO

(1) C2H6 (2) CH4 (3) CH3COOH (4) CH3COONa


Sol. Answer (2)
KMnO 4 H2SO4 NaOH
CH3  C  CH  CH3  COOH 
CaO
 CH4
(A) (B)

CH2 Turns CuSO4


crystal to blue
(1) KMnO4/
35. A + B + C ;
(2) H+

Turns lime H2O milky


Compound A, B and C are respectively
O O

(1) CH2O, H2O and (2) , CO2 and H2O


O CHO

(3) , SO2 and H2O (4) , CO2 and H2O

Sol. Answer (2)


CH2 O
(i) KMnO4/
+ CO2 + H2O
(ii) H+
A B C
lime water anhy. CuSO4

Milky Blue

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
42 Hydrocarbons Solutions of Assignment

CH3
CH3 (1) O3
36. C = C – CH = CH2 A + B + C;
CH3 (2) Zn/H2O

Which one is not A, B, C?

O O
(1) CH 3 – C – CH 3 (2) CH2O (3) CH 3 – C – CHO (4) CH3CHO

Sol. Answer (4)


CH3
CH3 (1) O3 CH3
C = C – CH = CH2 C = O + CH3 – C – CHO + CH2O
CH3 (2) Zn/H2O CH3
O
A B C

CH3
CH3 (1) O3
37. A + B + C ;
(2) Zn/H2O

A, B, C is/are

O O O
CHO
(1) CH3 – C – C – CH3 (2) (3) CH 3 – C – CHO (4) All of these
CHO
Sol. Answer (4)
CH3
CH3 CH3
(1) O3 C=O CHO
2 +
(2) Zn/H2O CHO CHO
CH3
CH3 CH3
(1) O3 C=O CHO
+2
(2) Zn/H2O C=O CHO
CH3

38. Baeyer’s reagent is


(1) 1% Alkaline KMnO4 (2) Acidic KMnO4 (3) Neutral KMnO4 (4) Aq. Br2 solution
Sol. Answer (1)
1% cold dilute alkaline KMnO4 is known as Baeyer's reagent.

39. Acetylene when oxidized with chromic acid gives


(1) Ethylene glycol (2) Oxalic acid (3) Formic acid (4) Acetic acid
Sol. Answer (4)

CH  CH 
H2CrO 4
[O]
 CH3  COOH
acetic acid

40. Benzene undergoes substitution reaction more easily than addition because
(1) It has a cyclic structure (2) It has three double bonds
(3) Of delocalization of electrons (4) It has six hydrogen atoms
Sol. Answer (3)
Benzene prefers to restore aromaticity.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 43
41. Ethylene + S2Cl2  "A". The compound "A" is
(1) Lewisite (2) Mustard oil (3) Mustard gas (4) Insecticide
Sol. Answer (3)
CH2 = CH2 CH2 – CH2 – Cl
+ S2Cl2 S +S
CH2 = CH2 CH2 – CH2 – Cl
(Mustard gas)

2+ +
Hg , H
42. Ph – C  CH + H2O "A" . The reaction is an example of
(1) Electrophilic addition (2) Nucleophilic addition
(3) Free radical addition (4) Electrophilic substitution
Sol. Answer (2)
In first step, Hg2+ adds to alkyne. Second step, H2O (nucleophile) attacks and adds to intermediate. Since
Hg2+ leaves as catalyst, hence, classification of nucleophilic addition reaction is more appropriate.

+
H
43. + CH3 – CH = CH2 A . Compound "A" is

(1) Isopropyl benzene (2) Cumene


(3) An alkyl derivative of benzene (4) All of these
Sol. Answer (4)
CH3
+
CH
H CH3
+ CH3 – CH = CH2
(Isopropyl benzene)
(cumene)

44. In sulphonation of benzene; electrophilic reagent used is

O
 
(1) SO3H (2) SO3 (3) O = S = O (4) SO2OH

Sol. Answer (2)



H 2SO 4 + H 2SO 4 SO3 + HSO4 + H 3O +
(Electrophile)

45. (CH3 )2 CHCH2Cl 


Anhydrous
 P (Major) . The product 'P' is
AlCl3

CH2CH(CH3)2 C(CH3)3 CH2(CH2)2CH3

(1) (2) (3) (4) All of these

Sol. Answer (2)


anhy. AlCl3
(CH3)2CHCH2Cl (CH3)2CH – CH2 + AlCl4
H shift
C(CH3)3
(CH3)3C
t-butyl benzne
(P)

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
44 Hydrocarbons Solutions of Assignment

46. Which one is o, p-directing group for electrophilic substitution reaction?

O O
CH3
(1) – C – OH (2) – C – NH2 (3) – N (4) – NO2
CH3
Sol. Answer (3)

CH3
Due to +M effect of – N group.
CH3

UV
47. Benzene  Cl2 
500 K
 A , A is

(1) Cyclohexane (2) Gammaxane (3) Chlorobenzene (4) 1,4-dichlorobenzene


Sol. Answer (2)

Cl
Cl Cl
UV
+ 3Cl2 500 K
Cl Cl
Cl
Benzene hexachloride (BHC)
or
Gammaxane

HI
48. CH3 – CH = CH – CH2 – CH3 A ;
Major
Compound "A" is

(1) CH3 – CH2 – CH – CH2 – CH3 (2) CH3 – CH – CH2 – CH2 – CH3

I I

CH3 CH3
(3) CH3 – C – CH2 – CH3 (4) CH3 – C – CH2I

I CH3

Sol. Answer (2)

H+ I–
CH3 – CH = CH – CH2 – CH3 CH3 – CH – CH2 – CH2 – CH3 CH3 – CH – CH2 – CH2 – CH3
(More stable)
I
(Major)

49. The electrophile which attacks in Friedel-Craft acylation is

O

O O
(1) R – C

(2) R – C (3) R – C – O (4) Both (1) & (3)
+

Sol. Answer (1)

O O
anhy. AlCl3
R – C – Cl R – C + AlCl4
(Electrophile)

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 45
50. Which of the following shows geometrical isomerism?
(1) But-1-ene (2) But-2-ene
(3) Prop-1-ene (4) Pent-1-ene
Sol. Answer (2)

CH3 H CH3 H
C C
and
C C
H CH3 CH3 H
trans-but-2-ene cis-but-2-ene

SECTION - B
Previous Years Questions
1. In the following reaction,

red hot
H3C – C  CH 
iron tube
873 K
A, the

number of sigma () bonds present in the product A, is [NEET-2019 (Odisha)]


(1) 18 (2) 21
(3) 9 (4) 24
Sol. Answer (2)

HC H
CH3 C – CH3 H3C
C Red Hot CH3
Iron tube
CH 873 K
CH H H
C
CH3
CH3
Number of 
bonds = 21

2. The most suitable reagent for the following conversion, is

H3C CH3
H3C C C CH3
H H
cis-2-butene

[NEET-2019]
(1) Na/liquid NH3
(2) H2, Pd/C, quinoline
(3) Zn/HCl
(4) Hg2+/H+, H2O
Sol. Answer (2)
H3C CH3
H2, Pd/C,
H3C C C CH3 C C
quinoline
H H
cis-2-butene

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
46 Hydrocarbons Solutions of Assignment

3. Among the following, the reaction that proceeds through an electrophilic substitution, is [NEET-2019]

+ –
Cu 2Cl2
(1) N2CI CI + N2

AlCl 3
(2) + Cl2 CI + HCl

CI CI

UV light
(3) + Cl2 CI CI

CI CI

(4) heat
CH 2OH + HCl CH 2Cl + H2O

Sol. Answer (2)

Cl

AlCl 3
+ Cl2 + HCl

Generation of electrophile:

.. + –
Cl Cl
.. + AlCl3 Cl Cl AlCl3
..

.. + –
Cl
.. + AlCl4
..

Electrophile

Cl H
+
Cl +
(i) etc

Cl Cl
H
+
(ii)

4. An alkene "A" on reaction with O3 and Zn–H2O gives propanone and ethanal in equimolar ratio. Addition of
HCl to alkene "A" gives "B" as the major product. The structure of product "B" is [NEET-2019]

CH3 CH 2Cl CH3 CH3


(1) Cl–CH2–CH2–CH (2) H3C–CH2–CH–CH3 (3) H3C–CH2–C–CH3 (4) H3C–CH–CH

CH3 Cl Cl CH3

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 47
Sol. Answer (3)
CH3 CH3
O3
C CH CH3 C O+ O CH CH3
Zn/H2O
(A) Ethanal
CH3 CH3
Propanone

HCl

CH3
C CH2 CH3
CH3 Cl
(B)
5. Hydrocarbon (A) reacts with bromine by substitution to form an alkyl bromide which by Wurtz reaction is
converted to gaseous hydrocarbon containing less than four carbon atoms. (A) is [NEET-2018]
(1) CH  CH (2) CH2  CH2
(3) CH4 (4) CH3 – CH3
Sol. Answer (3)

Na/dry ether
Br2/h Wurtz reaction
CH4 CH3Br CH3 — CH3
(A)

Hence the correct option is (3)


6. The compound C7H8 undergoes the following reactions [NEET-2018]
3Cl /  Zn/HClBr /Fe
C7H8 
2
 A 
2
 B  C

The product 'C' is


(1) m-bromotoluene (2) o-bromotoluene
(3) p-bromotoluene (4) 3-bromo-2,4,6-trichlorotoluene
Sol. Answer (1)

CH3 CCl3 CCl3 CH3

3Cl2 Br2 Zn
 Fe HCl
Br Br
(C7H8) (A) (B) (C)

7. Which of the following molecules represents the order of hybridisation sp2, sp2, sp, sp from left to right atoms?
[NEET-2018]
(1) HC  C – C  CH (2) CH2 = CH – C  CH
(3) CH3 – CH = CH – CH3 (4) CH2 = CH – CH = CH2
Sol. Answer (2)

sp2 sp2 sp sp
CH2  CH – C  CH

Number of orbital require in hybridization = Number of -bonds around each carbon atom.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
48 Hydrocarbons Solutions of Assignment

8. Predict the correct intermediate and product in the following reaction

H2O, H2SO4
H 3C C CH HgSO4
intermediate product [NEET-2017]
(A) (B)

(1) A : H3C C CH2 B : H3C C CH3 (2) A : H3C C CH2 B : H3C C CH2
SO4 O OH SO4

(3) A : H3C C CH3 B : H3C C CH (4) A : H3C C CH2 B : H3C C CH3

O OH O

Sol. Answer (4)

OH O
H2O, H2SO4 Tautomerism
H3C – C  CH H3C – C = CH CH3 – C – CH3
HgSO4
(A) (B)

9. Which one is the correct order of acidity? [NEET-2017]


(1) CH2 = CH2 > CH3 – CH = CH2 > CH3 – C  CH > CH  CH
(2) CH  CH > CH3 – C  CH > CH2 = CH2 > CH3 – CH3
(3) CH  CH > CH2 = CH2 > CH3 – C  CH > CH3 – CH3
(4) CH3 – CH3 > CH2 = CH2 > CH3 – C  CH > CH  CH
Sol. Answer (2)
Correct order is

H – C  C – H  H3C – C  C – H  H2C  CH2  CH3 – CH3


(Two acidic (One acidic
hydrogens) hydrogen)

10. With respect to the conformers of ethane, which of the following statements is true? [NEET-2017]
(1) Bond angle remains same but bond length changes
(2) Bond angle changes but bond length remains same
(3) Both bond angle and bond length change
(4) Both bond angles and bond length remains same
Sol. Answer (4)
There is no change in bond angles and bond lengths in the conformations of ethane. There is only change in
dihedral angle.
11. Which of the following can be used as the halide component for Friedel Crafts reaction?
[NEET(Phase-2)-2016]
(1) Chlorobenzene (2) Bromobenzene
(3) Chloroethene (4) Isopropyl chloride
Sol. Answer (4)

Isopropyl chloride would form stable carbocation H3C — C — CH3
H
Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 49
12. Which of the following compounds shall not produce propene by reaction with HBr followed by elimination or
direct only elimination reaction? [NEET(Phase-2)-2016]

H2 H2
(1) H2C CH2 (2) H3C C CH2OH (3) H 2C C O (4) H3C C CH2Br
C
H2
Sol. Answer (3)
H 2C C O , has only two carbon atom, cannot be converted into propene as the conditions are given.

HF
13. In the given reaction + P, the product P is [NEET(Phase-2)-2016]
0°C

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

Sol. Answer (3)

HF 
–H

14. The compound that will react most readily with gaseous bromine has the formula [NEET(Phase-2)-2016]
(1) C3H6 (2) C2H2 (3) C4H10 (4) C2H4
Sol. Answer (1)
In gas phase allylic substitution takes place.
15. The correct statement regarding the comparison of staggered and eclipsed conformations of ethane is
[NEET-2016]
(1) The staggered conformation of ethane is more stable than eclipsed conformation, because staggered
conformation has no torsional strain
(2) The staggered conformation of ethane is less stable than eclipsed conformation, because staggered
conformation has torsional strain
(3) The eclipsed conformation of ethane is more stable than staggered conformation, because eclipsed
conformation has no torsional strain
(4) The eclipsed conformation of ethane is more stable than staggered conformation even though the eclipsed
conformation has torsional strain
Sol. Answer (1)
Fact.
(1) NaNH2 /liq. NH3 (1) NaNH2 /liq. NH3
16. In the reaction, H – C  CH 
(2) CH CH Br
X 
(2) CH CH Br
Y . X and Y are [NEET-2016]
3 2 3 2

(1) X = 1-Butyne; Y = 2-Hexyne (2) X = 1-Butyne; Y = 3-Hexyne


(3) X = 2-Butyne; Y = 3-Hexyne (4) X = 2-Butyne; Y = 2-Hexyne

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
50 Hydrocarbons Solutions of Assignment

Sol. Answer (2)


(1) NaNH /liq. NH (1) NaNH2 /liq. NH3
H – C  CH 2
(2) CH3 CH2Br
3
H – C  C – CH2 – CH3  CH3 – CH2 – C  C – CH2 – CH3
(2) CH CH Br
(1Butyne (X)) 3 2
(3-Hexyne (Y ))

17. Consider the nitration of benzene using mixed conc. H2SO4 and HNO3. If a large amount of KHSO4 is added
to the mixture, the rate of nitration will be [NEET-2016]
(1) Doubled (2) Faster (3) Slower (4) Unchanged
Sol. Answer (3)

  –
HNO3  H2 SO 4 
 NO2  HSO 4  H2 O
 Addition of KHSO4 will decrease the NO2+ concentration.
18. 2,3-Dimethyl-2-butene can be prepared by heating which of the following compounds with a strong acid?
[Re-AIPMT-2015]
(1) (CH3)2C = CH – CH2 – CH3 (2) (CH3)2CH – CH2 – CH = CH2

(3) (CH3)2CH – CH – CH = CH2 (4) (CH3)3C – CH = CH2


CH3

Sol. Answer (4)

CH3 CH3
+
H +
CH3 – C – CH = CH2 CH3 – C – CH = CH2 (2° carbocation)
CH3 CH3 H

1, 2 – methyl shift

CH3 CH3
+
–H +
CH3 – C = C – CH3 CH3 – C – C – CH3 (3° carbocation;
more stable)
CH3 CH3 H
(2, 3 – Dimethyl-2-butene)
19. In the reaction with HCl, an alkene reacts in accordance with the Markovnikov's rule, to give a product 1-chloro-
1-methylcyclohexane. The possible alkene is [Re-AIPMT-2015]

CH2 CH3 CH3

(1) (A) (2) (B) (3) (A) and (B) (4)

Sol. Answer (3)


Markovnikov's rule more EN part attack's on unsaturated hydrocarbon which have less number of hydrogen.

CH2 CH3
Cl
HCl
AlC to M.R.

CH3 CH3
Cl
HCl
AlC to M.R.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 51
20. A single compound of the structure

CH3 CH3

OHC C C
H
C C O
H2 H2

is obtainable from ozonolysis of which of the following cyclic compounds? [AIPMT-2015]

H3C H3C CH3


H3C
(1) CH3 (2) CH3 (3) (4)
H3C
CH3
Sol. Answer (2)
CH3
CH3 CH3 CH3 CH3 CH3
O3 /Zn O O
O CH2
O O C

H
Or
CH3 CH3 CH3 CH3
O3/Zn O CH3 CH3
O or OHC CH2 CH C O

21. The reaction of C6H5CH = CHCH3 with HBr produces [AIPMT-2015]

CH = CHCH3

(1) (2) C6H5CHCH2CH3

Br
Br

(3) C 6H5CH2CHCH 3 (4) C6H5CH2CH2CH2Br

Br
Sol. Answer (2)
HBr + –
C6H5 CH CH CH3 C6H5 CH CH CH3
HBr

C6H5 CH CH2 CH3

Br

22. Which of the following organic compounds has same hybridization as its combustion product-(CO2) ?
[AIPMT-2014]
(1) Ethane (2) Ethyne (3) Ethene (4) Ethanol
Sol. Answer (2)

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
52 Hydrocarbons Solutions of Assignment

23. Some meta-directing substituents in aromatic substitution are given. Which one is most deactivating?
[NEET-2013]
(1) –SO3H (2) –COOH (3) –NO2 (4) –CN
Sol. Answer (3)
–NO2 group is the most deactivating group in aromatic substitution among the given options. Both N and O
are electron withdrawing elements and –NO2 shows –R effect.
24. Which of the following compounds will not undergo Friedal-Craft's reaction easily? [NEET-2013]
(1) Xylene (2) Nitrobenzene (3) Toluene (4) Cumene
Sol. Answer (2)
Friedel-Craft's reaction is an example of electrophilic substitution. Electron withdrawing group present on
benzene ring decreases the electron density over benzene ring and decreases the reactivity towards electrophilic
substitution. –NO2 group is an electron withdrawing substituent and hence it will deactivate benzene ring towards
Friedel-Craft's reaction.
25. Among the following compounds the one that is most reactive towards electrophilic nitration is
[AIPMT (Prelims)-2012]
(1) Toluene (2) Benzene (3) Benzoic acid (4) Nitrobenzene
Sol. Answer (1)
In toluene –CH3 is attached with benzene ring which increases the electron density over benzene ring due to
hyper-conjugation and +I effect. This makes benzene ring more reactive towards electrophilic substitution.
(–NO2) nitro and – (COOH) carboxylic acid group are electron withdrawing group and they will deactivate
benzene ring towards electrophilic nitration.

26. Which of the following reagents will be able to distinguish between 1-butyne and 2-butyne ?
[AIPMT (Mains)-2012]
(1) NaNH2 (2) HCl (3) O2 (4) Br2
Sol. Answer (1)
Terminal alkynes are acidic in nature and reacts with base because they contain acidic hydrogen.
CH3 – C  C – CH3 + NaNH2  No reaction.
CH3 – CH2 – C  CH + NaNH2  CH3 – CH2 – C CNa + NH3
Since 2-butyne does not contain acidic hydrogen, it will not react with base (NaNH2)
27. Which one of the following is most reactive towards electrophillic reagent? [AIPMT (Prelims)-2011]

CH3 CH3 CH3 CH3


(1) (2) (3) (4)
CH2OH OCH3 OH NHCOCH3

Sol. Answer (3)


This compound is most reactive towards electrophilic reagent because both –OH and CH3 are electron donating
substituents and +R effect of OH group is more than that of –OCH3, –CH2–OH and NHCOCH3

28. Liquid hydrocarbons can be converted to a mixture of gaseous hydrocarbons by [AIPMT (Prelims)-2010]
(1) Oxidation
(2) Cracking
(3) Distillation under reduced pressure
(4) Hydrolysis

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 53
Sol. Answer (2)
Distillation is a process of purification of liquids. The mixture of two liquid hydrocarbons can be seperated by
using distillation under reduced pressure. The reduced pressure allows the mixture to boil at lower temperature
which prevent the degradation of hydrocarbon.

29. The reaction of toluene with Cl2 in presence of FeCl3 gives 'X' and reaction in presence of light gives 'Y'. Thus, 'X'
and 'Y' are [AIPMT (Prelims)-2010]
(1) X = Benzal chloride, Y = o-chlorotoluene
(2) X = m-chlorotoluene, Y = p-chlorotoluene
(3) X = o-and p-chlorotoluene, Y = Trichloromethyl benzene
(4) X = Benzyl chloride, Y = m-chlorotoluene
Sol. Answer (3)
CH3 CH3 CH3
Cl
FeCl3
(i) + Cl3 and

Cl x (O– and p-chlortoluene)


CH3 CCl3
hv
(ii) + Cl2

Y (Trichloromethyl benzene)
In reaction I, electrophilic substitution is taking place where as in reaction II, free radical substitution is taking
place. Therefore In reaction I, substitution took place in the ring whereas in

30. In the following the most stable conformation of n-butane is [AIPMT (Prelims)-2010]
CH3 CH3 CH 3
H H CH3
H CH3 H
CH3

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


H H H H H
H
H CH3 H H H H H 3C H
Sol. Answer (2)
The anti conformer of n-butane is the most stable conformation, In anti conformation, the distance between
the two –CH3 groups is maximum and repulsion between electron charge cloud is minimum stability.

31. Benzene reacts with CH3Cl in the presence of anhydrous AlCl3 to form [AIPMT (Prelims)-2009]
(1) Chlorobenzene (2) Benzylchloride (3) Xylene (4) Toluene
Sol. Answer (4)
CH3
AlCl3
+ CH3–Cl + HCl

Toluene
+
Mechanism CH3 – Cl + AlCl3  CH3 + AlCl4–
CH3 CH3
+ H –
+ AlCl4
+ CH3 + AlCl3 + HCl

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
54 Hydrocarbons Solutions of Assignment

32. Nitrobenzene can be prepared from benzene by using a mixture of conc. HNO3 and conc. H2SO4 in the mixture,
nitric acid acts as a/an [AIPMT (Prelims)-2009]
(1) Acid (2) Base (3) Catalyst (4) Reducing agent
Sol. Answer (2)
33. Which one of the following is most reactive towards electrophilic attack? [AIPMT (Prelims)-2008]
Cl
CH2OH NO2 OH
(1) (2) (3) (4)

Sol. Answer (4)


The substituent attached with benzene ring are –Cl, CH2–OH, NO2 and –OH. In these substitutents –OH group
is the most electron donating substituent and increses electron density over benzene ring due to +R effect.
therefore, phenol C6H5OH is most reactive towards electrophilic attack.

34. The order of decreasing reactivity towards an electrophilic reagent, for the following would be
a. Benzene b. Toluene c. Chlorobenzene d. Phenol
[AIPMT (Prelims)-2007]
(1) d > b > a > c (2) a > b > c > d (3) b > d > a > c (4) d > c > b > a
Sol. Answer (1)
Phenol is more reactive than toluene towards electrophilic substitution reaction because +R effect of the –OH
group dominates order +I effect of –CH3 group and also phenol and toluene are more reactive than benzene
towards electrophilic substitution reaction because –OH and –CH3 both group are electron donating group.
Chlorobenzene is least reactive because of the electron withdrawing –I effect of Cl group.
35. Predict the product C obtained in the following reaction
HΙ  C
CH3CH2 – C  CH + HCl  B  [AIPMT (Prelims)-2007]

l
(1) CH3CH2 – C – CH3 (2) CH3 – CH – CH2CH2l
Cl Cl
l l

(3) CH 3 – CH 2 – CH 2 – C – H (4) CH3 – CH2 – CH – CH2Cl


Cl
Sol. Answer (1)


Cl
+
H + Cl
CH3–CH2–C CH CH3–CH2–C=CH2 CH3–CH2–C=CH2
Vinyl carbocation
Cl Cl Cl
H
+
I

CH3–CH2–C=CH2 CH3–CH2–C–CH3
CH3–CH2–C=CH3
+
I
36. Which one of the following alkenes will react fastest with H2 under catalytic hydrogenation conditions ?
[AIPMT (Prelims)-2005]
R H R R R R R R
(1) (2) (3) (4)
R H R R H H R H
(R = Alkyl substituent)

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 55
Sol. Answer (3)
Lesser the stability of alkene, higher is rate of hydrogenation also less substituted alkenes undergo hydrogenation
faster because steric hundrance is less.

R R R R
and are highly substituted, so they will undergo hydrogenation slowly.
R H R R

R R R H
will undergo hydrogenation faster than because one end of R2C = CH2 contains
H H R H
two alkyl group and it will hinder the approach of hydrogen involved in the hydrogenation.
37. Which is maximum stable?
(1) But-1-ene (2) cis-but-2-ene (3) trans-but-2-ene (4) All have equal
Sol. Answer (3)
More substituted alkene are more stable among as and trans isomer, trans isomer is more stable due to less
steric hindrance. Hence trans-but-2ene is more stable than cis-but-2ene and but-1-ene which is less substituted.

38. Geometrical isomers differ in


(1) Position of functional group (2) Position of atoms
(3) Spatial arrangement of atoms (4) Length of carbon chain
Sol. Answer (3)
Geometrical isomer have same molecular formula but different spatial arrangement by atoms/groups.
a a a b
C=C C=C
b b b a
cis trans

39. The correct order of reactivity towards the electrophilic substitution of the compounds aniline (I), benzene (II)
and nitrobenzene (III) is
(1) III > II > I (2) II > III I (3) I < II > III (4) I > II > III
Sol. Answer (4)
Presence of electron donating group increases the reactivity of benzene towards electrophilic substitution while
electron withdrawing groups decreases the reactivity of benzene towards electrophilic substitution.
Among aniline (I), benzene (II) and nitrobenzene, aniline is most reactive because of the presence of electron
releasing –NH2 group while nitrobenzene is least reactive due to the presence of electron withdrawing –NO2 group.
NH2 NO2

> >
Aniline Benzene Nitrobenzene

40. The reactive species in the nitration of benzene is

(1) NO3 (2) NO3 (3) NO2+ (4) NO2–

Sol. Answer (3)



HNO3 + H2SO4 HSO4 + NO2 + H2O
This NO2 ion acts as electrophile during the nitration of benzene.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
56 Hydrocarbons Solutions of Assignment

41. H3C CH CH CH2 + HBr  A

CH3

A (predominantly) is
(1) CH3 CH CH CH3 (2) CH3 CH CH2 CH2Br
CH3 Br CH3
Br

(3) CH3 C CH2CH3 (4) CH3 CH CH CH3


CH3 Br CH3
Sol. Answer (3)

H Br
H
  1, 2 hydride
 Br
CH3–CH–CH=CH2 CH3 C CH–CH3 CH3 C CH2–CH3 CH3 C CH2 CH3 A
Shift
CH3 CH3 CH3 CH3

42. The alkene R–CH = CH2 reacts readily with B2H6 and the product on oxidation with alkaline hydrogen peroxides
produces

(1) R C O (2) R CH CH2 (3) R–CH2–CHO (4) R–CH2–CH2–OH


CH3 OH OH
Sol. Answer (4)

B2H6 H2O2,OH
R–CH=CH2 THF
R–CH2–CH2–BH2 R–CH 2–CH2–OH

This is hydroboration of alkene which results in anti Markovnikov's additon of water to the alkene.

43. Electrophile in the case of chlorination of benzene in the presence of FeCl3 is


(1) Cl (2) FeCl3 (3) Cl+ (4) Cl–
Sol. Answer (3)
+ – + –
Cl2+FeCl2 Cl–ClFeCl3 Cl + FeCl4
The Cl+ generated acts as electrophile during chlorination.

44. The bond length between central carbon atom and other carbon atom is minimum in
(1) Propene (2) Propyne (3) Propane (4) Pentane
Sol. Answer (2)
The C–C bond length is strotest when both carbon atoms are bonded with a triple bond. Since propyne contains
a triple bond, it has minimum C–C bond length.

45. Which of the following is used as an anti-knocking material?


(1) Glyoxal (2) Freon
(3) T.E.L. (4) Ethyl alcohol
Sol. Answer (3)
T.E.L. is tetraethyl lead which is used as anti knocking additive for petrol (C2H5)4Pb - T.E.L.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 57
46. Which of the following reaction is expected to readily give a hydrocarbon product in good yields?
Cl C H OH
(1) CH3CH3 
2
 (2) (CH3 )3 CCl 2 
5

h

I2
(3) RCOOK   
Electrolys is
(4) RCOOAg 
Oxidation h

Sol. Answer (3)


Electrolysis of sodium or pottasium salt of carboxylic acid gives hydrocarbon in good yield. This method is
known as kolbe's electrolytic method
Electrolysis
2 R-COOK + 2H2O   R-R + 2CO2 + H2 + 2KOH

CH2OH
47. In a reaction : CH2  CH2    M 
Hypochloro us R
, where M = Molecule and R = Reagent. M and R
acid
CH2OH
are
(1) CH3CH2OH and HCl (2) CH3–CH3 and heat
(3) CH3CH2Cl and NaOH (4) CH2Cl–CH2OH and aq. NaHCO3
Sol. Answer (4)
Cl OH OH
Hypochlorous acid Aq. Na2CO3
CH2 = CH2 CH2–CH2–OH CH2–CH2
HOCl
M R

48. The cylindrical shape of alkyne is due to


(1) Two sigma C–C and one  C–C bonds (2) One sigma C–C and two  C–C bonds
(3) Three sigma C–C bonds (4) Three  C–C bonds
Sol. Answer (2)
R – C  C – R (Alkyne)
The cylindrical shape of the alkyne is due to triple bond which consist of one sigma and two  bonds. The
electron cloud between two carbon atoms is cylindrically symmetrical about the internuclear axis.
49. In the commercial gasolines, the type of hydrocarbons which are more desirable is
(1) Linear unsaturated hydrocarbon (2) Toluene
(3) Branched hydrocarbon (4) Straight-chain hydrocarbon
Sol. Answer (3)
For commercial gasolines branched hydrocarbons are more desirable because they react more rapidly with
oxygen and undergo combustion easily.
50. The most stable conformation of n-butane is
(1) Gauche (2) Staggered (3) Skew boat (4) Eclipsed
Sol. Answer (2)

CH3 CH3 H
CH3
H

H
H H H H
H CH3
Eclipsed form of n-butane staggered form of n-butane

Staggered form of n-butane is more stable because of minimum repulsion between the electron charge clouds
of C–H bond due to maximum distance between the groups.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
58 Hydrocarbons Solutions of Assignment

51. Which one of these is not compatible with arenes?


(1) Electrophilic additions (2) Delocalisation of -electrons
(3) Greater stability (4) Resonance
Sol. Answer (1)
Arenes are aromatic compound which are very stable due to their aromaticity. In arenes electrophilic substitution
is possible because substitution does not affect their aromaticity but addition will lead to disturbance of
aromaticity. Arenes show delocalization of -electron and are stable because of resonance but they will not
undergo electrophilic additions.

52. When acetylene is passed through dil. H2SO4 in the presence of HgSO4, the compound formed is
(1) Acetic acid (2) Ketone (3) Ether (4) Acetaldehyde
Sol. Answer (4)

2+
H
Hg tautomerise
HC CH + H2O H2SO4
CH2 = C – OH CH3 – CHO

53. In Friedel-Craft’s alkylation, besides AlCl3 the other reactants are


(1) C6H6 + CH3Cl (2) C6H6 + CH4 (3) C6H6 + NH2 – NH2 (4) C6H6 + CH3COCl
Sol. Answer (1)

CH3
AlCl3
+ CH3Cl + AlCl3 + HCl
(C6H6)
Friedel craft's alkylation

54. Gammexane is
(1) Bromobenzene (2) Benzyl Chloride
(3) Chlorobenzene (4) Benzene hexachloride
Sol. Answer (4)
Cl
Cl Cl

Cl Cl
Cl
Benzene hexachloride (gammexane)
55. In Friedel-Crafts reaction, toluene can be prepared by
(1) C6H6 + CH3Cl (2) C6H5Cl + CH4 (3) C6H6 + CH2Cl2 (4) C6H6 + CH3COCl
Sol. Answer (1)
+ –
CH3–Cl + AlCl3 CH3 + AlCl4

+ CH3 CH3
AlCl4
+ CH3 + + AlCl3 + HCl
H
Toluene
56. 2-butene shows geometrical isomerism due to
(1) Restricted rotation about double bond (2) Free rotation about double bond
(3) Free rotation about single bond (4) Chiral carbon

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 59
Sol. Answer (1)
CH3 CH3 H CH3
C=C C=C
H H CH3 H
cis-but-2-ene trans-but-2-ene
In alkene geometrical isomerism is possible due to restricted rotation about the double bond. Due to this restricted
rotation, cis and trans form are not readily convertible into other and exist as pair of geometrical isomers.
57. Dihedral angle in staggered form of ethane is
(1) 0° (2) 120° (3) 60° (4) 180°
Sol. Answer (3)
H Dihedral angle (60°)

H H

H H
H
Staggered form of ethane

58. Which alkene on ozonolysis gives 'CH3CH2CHO and CH3CCH3 ?


||
O

CH3
(1) CH3CH2CH C
||

(2) CH3CH2CH = CHCH2CH3


CH3

(4) CH3 – C CHCH3


||
(3) CH3CH2CH = CHCH3
|
CH3

Sol. Answer (1)


CH3 O CH3
O3 Zn/H2O
CH3–CH2–CH=C CH3–CH2–CH C
CH3 CH3CH2CHO + CH3COCH3
CH3
O O

59. In preparation of alkene from alcohol using Al2O3 which is the effective factor?
(1) Porosity of Al2O3 (2) Temperature
(3) Concentration (4) Surface area of Al2O3
Sol. Answer (2)
Dehydration of alcohol in presence of Al2O3 gives alkene. Al2O3 acts as a catalyst and rate of the reaction of
affected by the temperature.

CH3
60. The compound CH3 C CH CH3 on reaction with NaIO4 in the presence of KMnO4 gives
(1) CH3COCH3 (2) CH3COCH3 + CH3COOH
(3) CH3COCH3 + CH3CHO (4) CH3CHO + CO2
Sol. Answer (2)
CH3
NaIO4 [O]
CH3 C CH CH3 CH3COCH3 + CH3CHO CH3COOH
KMnO4
Initially CH3CHO is formed but since KMnO4 is a strong oxidizing agent, it oxidizes CH3CHO to CH3COOH.
Therefore products are CH3COCH3 and CH3COOH.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
60 Hydrocarbons Solutions of Assignment

(i) O / ether
61. Products of the following reaction CH3 C  CCH2 CH3  
3
  are
(ii) H2 O / Zn

O O

(1) CH3 – C – C – CH2 – CH3 (2) CH3COOH + HOOC.CH2CH3


(3) CH3CHO + CH3CH2CHO (4) CH3COOH + CH3COCH3
Sol. Answer (1)
O O O
(i) O3/ether (ii) Zn/H2O
CH3–CC–CH2–CH3 CH3–C – C–CH2–CH3 CH3–C–C–CH2–CH3
O O

62. Which of the compounds with molecular formula C5H10 yields acetone on ozonolysis?
(1) 3-methylbut-1-ene (2) Cyclopentane (3) 2-methylbut-1-ene (4) 2-methylbut-2-ene
Sol. Answer (4)
CH3 CH3 O O
O3 Zn
CH3–C=CH–CH3 CH3–C – CH–CH3 H2 O
CH3–C–CH3 + CH3–CHO
O O

Hence 2-methyl but-2-ene will give acetone on ozonolysis


63. One of the following which does not observe the anti-Markownikoff’s addition of HBr, is
(1) Pent-2-ene (2) Propene (3) But-2-ene (4) But-1-ene
Sol. Answer (3)
Br
CH 3–CH =CH–CH3 + HBr CH 3–CH 2–CH–CH 3
Symmetrical alkenes do not show anti-markovnikov's addition
64. Given
Br Br H Br
H H
CH3
and
CH3 CH3 CH3
H
Br
I II
I and II are
(1) A pair of optical isomers (2) Identical
(3) A pair of conformers (4) A pair of geometrical isomers
Sol. Answer (3)
Compound I and II are a pair of conformers. They are not geometrical isomers because they do not contain
double bond also not optical isomers because carbon-2 and 3 contain same groups. These are a pair of
conformers because they are redaily interconvertible into one another just by the rotation about C–C bond.
65. Which of the following conformers for ethylene glycol is most stable?

OH OH OH
OH H
H H
(1) (2) (3) (4)
H H H HO
H H H H
OH H H
Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 61
Sol. Answer (4)
The gauche conformers of ethylene glycol is the most stable conformation because of intramolecular H-bonding

H
–H–bond

Gauche conformer

This type of hydogen bonding is possible only in gauche conformer. Therefore it is the most stable conformation
of ethylene glycol.

66. Reaction of HBr with propene in the presence of peroxide gives


(1) Isopropyl bromide (2) 3-bromo propane
(3) Allyl bromide (4) n-propyl bromide
Sol. Answer (4)
peroxide
CH3 – CH = CH2 + HBr   CH3 – CH2 – CH2 – Br (n-propyl bromide)

In the presence of peroxide, addition of HBr to unsymmetrical alkene follows anti markovnikov's rule. Due to
the free radical addition. In presence of peroxide HBr dissociates into radicals.

67. Which one of the following is a free-radical substitution reaction?

CH3 Boiling CH2Cl Anh. AlCl3 CH3


(1) + Cl2 (2) + CH3Cl

CH2Cl CH2NO2
(3) + AgNO2 (4) CH3CHO + HCN  CH3CH(OH)CN

Sol. Answer (1)

Cl2 2Cl
CH3 CH2 CH2 CH2Cl
+ Cl + HCl + Cl2
Benzyl radical

68. Using anhydrous AlCl3 as catalyst, which one of the following reactions produces ethylbenzene (PhEt)?
(1) H3C – CH2OH + C6H6 (2) CH3 – CH = CH2 + C6H6
(3) H2C = CH2 + C6H6 (4) H3C – CH3 + C6H6
Sol. Answer (3)

AlCl3 
CH2 = CH2 + H+   CH2 – CH3

CH2–CH3 CH2–CH3
 –H
+
+ CH2 – CH3 
H
Ethyl benzene

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
62 Hydrocarbons Solutions of Assignment

ether HCl
69. Given reaction Br Mg X H2O Y(main product) Y in the reaction is

(1) Hexane (2) Cyclohexane


(3) Cyclohexylcyclohexane (4) Cyclohexylether
Sol. Answer (2)
– +
ether HCl
Br Mg
MgBr H2O H + Mg(OH)Br

X Y(cyclohexane)

70. Monobromination of 2-methylbutane gives how many distinct isomers?


(1) One (2) Two (3) Three (4) Four
Sol. Answer (4)
Four isomers of 2-methyl butane is formed on monobromination. These are
CH3 CH3 CH3 CH3

CH3 C CH2 — CH2 — Br CH3 C CH — CH3 CH3 C CH2 — CH3 CH2 C CH2 — CH3

H H Br Br Br H
(I) (II) (III) (IV)

71. When CH3CH2CHCl2 is treated with NaNH2, the product formed is


(1) CH3 – CH = CH2 (2) CH3 – C  CH

NH2 Cl
(3) CH 3CH 2CH (4) CH3CH2CH
NH2 NH2

Sol. Answer (2)


NaNH2
CH3 – CH2 – CHCl2  CH3 – C  CH
Vicinal dihalides undergo elimination in the presence of a strong base to give alkyne.

72. 2-Bromopentane is heated with potassium ethoxide in ethanol. The major product obtained is
(1) trans-pent-2-ene (2) Pent-1-ene (3) 2-ethoxypentane (4) cis-pent-2-ene
Sol. Answer (1)

Br Br
E2 CH3 H
CH3–CH–CH–CH2–CH3 CH3–CH – CH–CH2–CH3 Elimination C=C
H CH2– CH3
H H OC2H5 Trans-pent-2-ene
OC2H5

Anti elimination leads to the formation of trans product

73. An organic compound A(C 4 H 9 Cl) on reaction with Na/diethyl ether gives a hydrocarbon which on
monochlorination gives only one chloro derivative then, A is
(1) t-butly chloride (2) Secondary butyl chloride
(3) Iso butyl chloride (4) n-butyl chloride
Sol. Answer (1)

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 63
74. In the following reaction
1. Mg, Ether
C6H5 CH2Br  
 X,
2. H3O

the product ‘X’ is


(1) C6H5CH2OCH2C6H5 (2) C6H5CH2OH
(3) C6H5CH3 (4) C6H5CH2CH2C6H5
Sol. Answer (3)

– +
CH2Br CH2 Mg Br CH3

Mg/Ether H3O
+ Mg(OH)Br

In the presence of acid, grignards reagent gives the corresponding alkane by abstraction proton from the acid.

75. When 3, 3-dimethyl 2-butanol is heated with H2SO4, the major product obtained is
(1) 2, 3-dimethyl 2-butene (2) cis and trans isomers of 2, 3-dimethyl 2-butene
(3) 2, 3-dimethyl 1-butene (4) 3, 3-dimethyl 1-butene
Sol. Answer (1)

CH3 CH3 CH3


H2SO4 –H2O  1, 2-methyl
CH3 C CH — CH3 CH3 C CH — CH3 CH3 C CH — CH3
shift

CH3 OH CH3 OH2 CH3
2º carbocation

CH3
 
–H
CH3 C C — CH3 CH3 C C — CH3

CH3 CH3 CH3


3°-carbocation 2,3-dimethyl 2-butene

This reaction is dehydration of alcohol which involves rearrangement.

76. Identify Z in the sequence of reaction


HBr
CH3 – CH2 – CH  CH2 
H O /h
Z
2 2

(1) CH3 CH2 CH CH3 (2) CH3 – CH2 – CH2 – CH2 – Br


Br

(3) CH3 CH CH CH2 (4) None of these


Br
Sol. Answer (2)
HBr
CH3 –CH2 – CH = CH2 
H O /hv
 CH – CH – CH – CH – Br
3 2 2 2
2 2

Addition of HBr to unsymmetrical alkene follow free radical mechanism and the addition is anti markovnikov's
addition.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
64 Hydrocarbons Solutions of Assignment

CH3
H2O/H
77. In the following reaction : H3C–C–CH = CH2 A + B
(Major (Minor
CH3 Product) Product)

The major product is


CH3 CH3

(1) H3C–C – CH–CH3 (2) H3C–C – CH2–CH2


CH3 OH CH3 OH
CH3 CH3

(3) H3C–C – CH–CH3 (4) CH2–C–CH2–CH3

OH CH3 OH CH3
Sol. Answer (3)
CH3 CH3 CH3

H  1,2-methyl 
CH3–C – CH=CH2 CH3–C – CH – CH3 shift CH3–C – CH – CH3

CH3 CH3 CH3


2° carbocation 3° carbocation
H2O H2O
CH3 CH3
CH3–C – CH–CH3 CH3–C – CH–CH3

CH3 OH2 OH2 CH3
 
–H –H

CH3 CH3

CH3–C – CH–CH3 CH3–C – CH–CH3

CH3 OH OH CH3

Tertiary (3°) carbocations are more stable than a secondary (2°) carbocation. Therefore rearrangement takes
place to give 3° carbocation and major product is formed from it.

78. What products are formed when the following compound is treated with Br2 in the presence of FeBr3?
CH3

CH3
CH3 CH3 CH3 CH3
Br Br Br
(1) and (2) and
CH3 CH3 CH3 CH3
Br
CH3 CH3 CH3 CH3
Br
(3) and (4) and

CH3 CH3 CH3 Br CH3


Br Br
Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 65
Sol. Answer (3)
CH3 CH3 CH3
Br
Br2/FeBr3
+
Ortho and para directing
CH3 CH3 CH3
Br

79. Which of the following chemical system is non-aromatic?

(1) (2)

(3) (4)
S
Sol. Answer (1) 3
sp
Cyclopentane-1, 3-diene is a non aromatic compound since cyclic delocalization of 2 2
sp sp
electron is not possible because of the presence of sp3 hybridized carbon atom. sp
2 2
sp

80. Which one of the following compounds will be most easily attacked by an electrophile?

CH3
(1) (2)

Cl OH
(3) (4)

Sol. Answer (4)


Among the substituent attached with benzene ring, –OH is the most electron donating substituent. Therefore,
phenol C6H5OH will be most reactive towards electrophilic substitution reaction. +R effect of –OH is stronger
than that of –CH3 and –Cl
81. Increasing order of electrophilic substitution for following compounds

CH3

I. II.

OCH3 CF3

III. IV.

(1) IV < I < II < III (2) III < II < I < IV
(3) I < IV < III < II (4) II < III < I < IV
Sol. Answer (1)
Rate of electrophilic substitution depends on the electron density present over benzene ring. Among the
substituent present on benzene ring, their electron donating ability (+R effect) is in the order –OCH3>–CH3–
>–CF3. –CF3 is an electron withdrawing substituent. It will deactivate the benzene ring towards electrophilic
substitution. Therefore, correct order of electrophilic substitution
IV < I < II < III

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
66 Hydrocarbons Solutions of Assignment

82. Among the following compounds (I-III) the correct order of rate of electrophillic substitution is

OCH3 NO2

I II III

(1) I > II > III (2) I = II > III


(3) II > III > I (4) III < I < II
Sol. Answer (1)
Electron donating substituent attached with benzene ring increases the reactivity of benzene towards
electrophilic substitution while electron withdrawing substituent attached to benzene ring decreases the reactivity
of benzene ring towards electrophilic substitution reaction. –OCH3 is an electron donating substituent while –
NO2 is an electron withdrawing substituent hence, the correct order is I > II > III

SECTION - C

Assertion-Reason Type Questions

1. A : CHC–CH2–CH=CH2 adds up HBr to give CHC–CH2–CH–CH3 while CHC–CH=CH2 adds up HBr to give
|
Br
CH2=C–CH=CH2
|
Br

R : Double bond is always more reactive than triple bond towards electrophillic addition reaction.
Sol. Answer (3)
Alkenes are more reactive than alkynes and addition of electrophilic reagent takes place preferably at double
bond when both double and triple bond are present in the substrate. When electrophile add to alkyne, vinylic
cation is formed which is highly unstable on the other hand addition of electrophile to alkene forms alkyl radicals
which are more stable vinyl cations. Therefore alkenes are more reaction.
Hence assertion is true but reason is false.

2. A : In alkene, hydroboration oxidation process is an example of pericyclic reaction.


R : BH3 forms the cyclic transition state with double bond.
Sol. Answer (1)
The hydroboration of alkene is an example of pericyclic reaction. Pericyclic reactions are concerted reaction
wich proceeds through cyclic transition state.
Therefore both assertion and reason are true.

CH3
|
3. A : When isobutane is reacted with Cl2 in presence of sunlight then CH3–CH–CH2Cl is formed in high
percentage.
R : The reactivity of 1°, 2° & 3° H-atoms towards chlorine are 1 : 3.8 : 5 respectively.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 67
Sol. Answer (2)
Assertion is true because ratio of selectivity for 3° carbon to 1° carbon is 5:1
Total selectivity for 1° carbon for 1° carbon = 9 × 1 = 9
Total selectivity for 3° carbon = 5 × 1 = 5
Hence reason is also true but not the correct explanation of assertion.

4. A : On dehydration with concentrated H2SO4, neopentyl alcohol gives 2-methyl butene-2.


R : 3° carbocation is more stable than 2° carbocation.
Sol. Answer (2)

CH3 CH3 CH3


H

 –H2O 
1,2-methyl
CH3–C – CH2–OH CH3–C – CH2 – OH2 CH3–C – CH2
shift
CH3 CH3 CH3


 –H
CH3–C – CH2 – CH3 CH3–C = CH – CH3

CH3 CH3

Assertion is true because neopentyl alcohol gives 2-methyl but-2ene on dehydration and reason is also true
that 3°carbocation is more than 2° carbocation but is is not the correct explanation of assertion.

5. A : Generally, n-hexane and onwards can be sulphonated but isobutane and isopentane can also be
sulphonated.
R : Isobutane and isopentane can produce tertiary free radical.
Sol. Answer (1)
n-hexane, isobutane and isopentane can be sulphonated. Isobutane and isopentane forms tertiary radicals and
tertiary radicals are stable. Since these compound gives stable inter mediate they can undergo sulphonation.
Hence both assertion and reason are true and reson is the correct explanation of assertion.

6. A : When 2-fluorobutane is reacted with alcoholic KOH then butene-1 is formed as major product.
R : Butene-2 is more stable than butene-1.
Sol. Answer (2)
When 2-fluorobutane is reacted with alcoholic KOH 1-butane is formed as major product because presence
of fluorine stabilizes the intermediate which lead to formation of less substituted alkene

F F
– –
CH3 – CH2 – CH – CH2 CH3 – CH – CH – CH3
– –
(I) H H OC2H5
OC2H5
(II)

7. A : When butyne-2 is reacted with Na/liq. NH3 then trans-butene-2 is formed.


R : This reaction proceeds through free radical intermediate.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
68 Hydrocarbons Solutions of Assignment

Sol. Answer (2)


Assertion is true that reduction of 2-butyne with Na/Liq. NH3 gives trans-2-butene as reduction of alkyne with
Na/liq NH3 gives trans alkene.
Reason is also that reduction with Na/liq NH3 follows free radical mechanism but reason is not the correct
explanation of assertion.

8. A: has 12  electrons i.e. 4n  electrons.

R : It is an antiaromatic compound.
Sol. Answer (3)
Assertion is true because the two benzene ring totally contains 12 electrons but the compound is not anti
aromatic because both ring are joined by a double bond and aromaticity is maintained individually by each
ring having 6 electron (4n + 2) electrons. So reason is false

9. A : Propene reacts with HBr in presence of H2O2 gives 2-bromopropane as a major product.
R : This reaction proceeds always through 2° free radical as intermediate.
Sol. Answer (3)
The addition of HBr to propene in presence of H2O2 gives 2-bromopropane as major product. Hence assertion
is true. This addition takes place through the formation of 1° radical, so reason is false.

CH3 – CH = CH2 + Br CH3 – CH – CH2


Br 1º radical

CH3 – CH – CH2 + HBr CH 3 – CH – CH 3 + Br


Br Br

10. A : Boiling point of n-pentane is more than neopentane but the melting point of neopentane is more than n-
pentane.
R : Branching decreases the boiling point but increases the melting point.
Sol. Answer (3)
Boiling point of a hydrocarbon depend on the magnitude of van der Waals forces which is maximum for linear
hydrocarbons so n-pentane has higher B.P. than neopentane but melting point depend on the packing of the
constituent molecules and more spherical molecules are more tightly packed. Since neopentane is spherical
shaped due to branching, it has higher melting point then n-pentane.

11. A : Alkynes is more reactive than alkene towards electrophilic addition reaction.
R : Alkynes form stable carbocation than alkene.
Sol. Answer (4)
Alkynes are less reactive than alkenes because addition of electrophile to alkyne gives vinyl cation which is
unstable while additon of electrophile to alkene give alkyl carbocation which is more stable than vinylcation.
So assertion is false reason is also false because alkene gives alkyl carbocation which is more stable than
vinylcation.
Hence reason is also false.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 69

12. A : on reaction with Na/NH3 gives as major product.

R : This reaction occurs through the formation of carbocation intermediate.


Sol. Answer (3)
The product of the reaction of benzene with Na/liq. NH3 gives 1,4-cyclohexadiene.

Na/liqNH3

This reaction does not involve the formation of carbocation, as this reaction follows free radical mechanism.
Therefore assertion is true, reason is false.
13. A : But-1-yne has acidic hydrogen but but-2-yne does not.
R : In but-1-yne hydrogen atom is attached with sp hybridised carbon but no hydrogen is attached with sp
hybridised carbon in but-2-yne.
Sol. Answer (1)
In but-2-yne both the sp hybridized carbon which are electronegative, they are attached to methyl group while
in but-1-yne the terminal sp hybridized carbon is attached to a hydrogen which can be released due to the
high electronegativity of sp hybridized carbon.

– +
CH3 – C  C – CH3 CH3 – CH2 – C  C – H
But-2-yne But-1-yne

Therefore both assertion and reason are true and reason is correct explanation of assertion.

14. A : CH3 CH2 CH CH3 on reaction with KNH2 gives but-1-ene as major product.

F
R : It follows E1CB mechanism.
Sol. Answer (1)
When a highly electron withdrawing group is attached with alkyl group, elimination reaction proceeds through
the formation of stable carbanion as intermediate.

F F F
Na/NH2
CH3 – CH2 – CH – CH3 CH3 – CH – CH – CH3 and CH3 – CH2 – CH – CH2
(I) (II)

Since II is more stable carbanion,elimination from II will give but 1-ene. This reaction gollows E1CB mechanism
because it involves formation of carbanion as intermediate. Hence both assertion and reason are true.

15. A : Methane cannot be prepared by kolbe electrolytic reaction.


R : In this reaction alkane is liberated at anode.
Sol. Answer (2)
Methane cannot be prepared by kolbe's electrolytic method because the alkane formed in kolbe's electrolytic
method contains even number of carbon atom due to combination of alkyl radicals. The alkane formed is
liberated at anode during the reaction.
Hence assertion and reason are true but reason is not the correct explanation of assertion.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
70 Hydrocarbons Solutions of Assignment

16. A : Benzene on reaction with V2O5 gives maleic anhydride at high temperature.
R : V2O5 act as reducing agent.
Sol. Answer (3)
Benzene on oxidation with V2O5 gives maleic anhydride at high temperature
O
V2O5 CH C
O
CH C
O
maleic anhydride

V2O5 acts as oxidizing agent. Assertion is true but reason is false.

17. A : The rate of sulphonation of benzene and deutrobenzene is different in the presence of oleum.
R : The slow step is the breaking of C—H or C—D bond.
Sol. Answer (1)
In sulphonation of benzene and deuterobenzene, C–H and C–D bond are broken respectively. The rate of a
reaction depend on the slowest step and in sulphonation of benzene and deuterobenzene, breaking of C–H
and –C–D bond is the slow step and hence rate of reaction is different for both benzene and deuterobenzene.

18. A : Friedel-crafts alkylation of benzene occurs in the presence of Lewis acid.


R : The function of Lewis acid to generate electrophile.
Sol. Answer (1)
During the alkylation of benzene through friedel craft's reaction the lewis acid reacts with the alkyl halide and
generates electrophile CH3 – Cl + AlCl3  CH3 + AlCl4–
AlCl3 is a lewis acid and CH3 is the electrophile.

19. A : The reaction between benzene and (CH3)3C  COCl in the presence of anhyd AlCl3 gives ter-butyl benzene
as major product.
+ +
R : (CH3)3C  CO is formed first which converted into more stable (CH3)3C by liberating CO.

Sol. Answer (1)

O O
(CH3)3C – C – Cl + AlCl3 (CH3)3C – C + AlCl4

O CH3
(CH3)3C – C CH3– C + CO
CH3

CH3
CH3
C – CH3
+ CH3 – C
CH3
CH3
ber-butylbenzene

O O
(CH3)3C – C carbocation is not as stable as ter-carbocation therefore (CH3)3C – C eliminates CO to form
more stable 3° carbocation.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Solutions of Assignment Hydrocarbons 71
20. A : Addition of Br2 in trans-but-2-ene in the presence of CCl4 gives meso form.
R : The reaction occurs through anti addition.
Sol. Answer (1)
Trans-but-2-ene on undergoes anti addition of bromine to gives meso compound. Addition of bromine to alkene
first form cyclic bromonium ion and then backside attack of Br takes place and thus anti addition results
in the formation of meso product

Br
C–C

– C – Br
Br Br – C –
Meso product

21. A : Cyclohexane is more stable than cyclopentane.


R : According to Baeyer strain theory angle strain in cyclohexane is more than cyclopentane.
Sol. Answer (2)
According to baeyer strain theory angle strain is more in cyclohexane than cyclopentane but cyclohexane
is more stable than cyclopentane because cyclohexane ring is puckered in which all the angles are tetrahedral
hence stable.

22. A : Addition of HBr in buta-1, 3-diene gives 3-bromo-but-1-ene as major product at low temperature.
R : Addition of HBr in buta-1, 3-diene gives 1-bromo-but-2-ene as major product at high temperature.
Sol. Answer (2)
Addition of HBr to 1, 3-butadiene gives 3-bromo-but-1-ene as major product at low temperature because at low
temperature this reaction follows electrophilic additon but higher temperature HBr dissociates to form free radical
and 1-bromo-but-2-ene is formed as major product due to allylic delocalization.

23. A : Gauch conformer of ethylene glycol is most stable.


R : It is due to the formation of intramolecular hydrogen bonding.
Sol. Answer (1)
Gauch conformers of ethylene glycol is mor stable than other conformations due to intramolecular hydrogen
bonding

24. A : But-2-ene is more stable than propene.


R : Heat of hydrogenation of but-2-ene is lesser than that of propene.
Sol. Answer (1)
Lesser the heat of hydrogenation of an alkene, more is the stability heat of hydrogenation of but-2-ene is lesser
than that of propane. Hence but-2-ene is more stable.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
72 Hydrocarbons Solutions of Assignment

25. A : Grignard reagent on reaction with alcohol form alkane.


R : Alcohol has acidic (active) hydrogen.
Sol. Answer (1)
Grignards reagent acts as a base and abstracts a proton from a species containing acidic hydrogen to give
– +
alkane CH3CH2MgBr + C2H5OH CH3CH2–H + MgBr (OC2H5) . The alcohol can acts as an acid due to
the polarity of O–H bond.
26. A : Phenol is more reactive than toluene towards SE reaction.
..
R : OH
.. group shows +R and +I both effects.
Sol. Answer (3)
Phenol is more reactive than toluene towards electrophilic substitution reaction because of the +R effect of
the –OH group. –OH shows +R effect and –I effect but –CH3 has +I effect and +R effect of –OH dominates
over +I effect of –CH3 group. Therefore, assertion is true but reason is false.

  

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456

You might also like