Hydrocarbon

Solution
Exercise Type Specific No. of Questions
Ex-O1 SOT 15
Ex-O2 MAT 10
Ex-S1 Subjective 28
Ex-03 JEE-Mains Objective 40
Ex-03 JEE ADV Objective 35

Total Que. 128

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ALLEN Hydrocarbon 1

HYDROCARBON
SOLUTIONS
EXERCISE # O-1
1. (A)
In Kolbe's electrolytic method at cathode NaOH is form so pH of solution increases as electrolysis
process.
2. (C)
Br — CH2 — CH2 — CH2 — Br Na
ether

Intramolecular
Na ® Na + e
+ –

free radical mech. CH2 — CH2 — CH2

3. (B)

NBS

Br
Br Br
Br

4. (C)
Br Br
Br Br
Br2
+
* *
2 2
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5. (C)
1
It is pyrolysis of ester rate µ
Steric Crowding

H H H H
b
Ph CH3 Ph CH3 Ph CH3– Ph CH3
D Br2 NaI
CH3 CCl4 CH2 Acetone
Ph CH2 Br CH2
b H O—C—R Ph b Ph Ph
O

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2 JEE-Chemistry ALLEN
6. (B)
Anti Markownikoff's addition not observed in symmetrical alkene

HBr
H3C — CH = CH — CH3 ¾¾ ¾
HBr
® H3C — CH = CH — CH3

Br

HBr
Peroxide No effect
Br
7. (A)
Br
H
alc. KOH
D

E2 mech. no possibility of rearrangement

8. (D)
Reaction of Bromine with unsaturated compound is example of electrophilic addition reaction.
The unsymmetrical alkenes are more reactive than symmetrical alkene towards electrophilic addition.
So, Ans. [D] H3C — C = CH2
H
Br2
H3C — C = CH2 H3C — C — CH2 + Br
+
H H Br

Br
H3C — C — CH2
Br
9. (D)
In the ionic reaction of HCl with alkene carbocation is formed as intermediate [Electrophilic addition]
so order of reactivity depends of stability of respective carbocation
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10. (C)
d-block metal containing reagant give system addition.

CH3
H3 C CH3 Cold alkaline
C=C KMnO4 H — C — OH
H H
[Baeyar’s H — C — OH
reagent]
CH3

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ALLEN Hydrocarbon 3
11. (D)
[Kucheror reaction] [Non resolrable]
OH O
HgSO4(aq) Tautomerisation
H2SO4die
OH

12. (C)
+
CH2OH CH2
H+/D
–H2O

ring expansion

Br
+
NBS D
–H+
major
13. (C)

14. (B)
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15. (C)

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ALLEN Hydrocarbon 1

EXERCISE # O-II
1. (B)

2. (A,B,C,D)

So, Ans. (A), (B), (C), (D)

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3. (A,B)

Selective Bromination at allylic carbon.

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2 JEE-Chemistry ALLEN
4. (B,C)

So, Ans: (B), (C)

5. (B,C,D)

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6. (A,C)
Symmetrical alkene given similar product
H H
HBr HBr
(A) with peroxide In alkene of peroxide
Br Br

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ALLEN Hydrocarbon 3

H H
HBr HBr
(B) with peroxide In absence of peroxide
Br Br
So, Ans: (A), (C)

7. (A,B,D)

(B)

(D)

8. (A,C)
When both are symmetrical
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(A)

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4 JEE-Chemistry ALLEN

H3C — C º C — CH3

F
TH
HgSO4(aq)

H
H2SO4(dil)

2 /O
—
HO
3
BH

2
(C) H3C — C = C — CH3 H3C — C = C — CH3
H OH H OH
Tautomerisation Tautomerisation
O O
H3C — C — C — CH3 H3C — CH2 — C — CH3

H2

9. (A)®P ; (B)®R ; (C)®S ; (D)®Q

Br
(A) CH3 — C = CH2 HBr H3C — C — CH3
H H
HBr
(B) H3C — C = CH2 Peroxide H3C — C — CH2 — Br
H H2
Br
(C) H3C — C = CH2 NBS H2C — C = CH2
H H2

H Cl
Br2
(D) H3C — C = CH2 CCl4
H2C — C — C
H Cl H2
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So, Ans: (A)®P ; (B)®R ; (C)®S ; (D)®Q

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10.

So,
(C)
(B)
ALLEN

(D)
(A)
®

(A)®R ; (B)®S ; (C)®Q ; (D)®P

Ans: (A)®R ; (B)®S ; (C)®Q ; (D)®P

Hydrocarbon
5
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ALLEN Hydrocarbon 1

EXERCISE # S-1
1. (D)
2. (B)

OH
HÅ
–H2O

1,2-shift

1,2-shift Ring
Expansion

O3/Zn
(B) Option
H2O
(Ozonolysis)
(A)

3. (A)

OH
CH3
(i) CH3MgBr
O +
(ii) H3O H2SO4 / D
Dehydration
(A) of
Alcohol
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O O
OZonolysis (B)
O3/Zn, H2O

(C)

4. (C)
HOH µ unstability of alkene

5. (B)
R1 : Bayer's reagent (Cold alkaline KMnO4); do syn addition of –OH group.
R2: Peroxy acid (HCO3H) followed by hydrolysis do anti addition of –OH group.

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2 JEE-Chemistry ALLEN
6. (A)
– Peroxy acid do anti addition of OH ; after hydrolysis.

7. (B)

KMnO4/OH
CH3 – C = CH2 CH3 – C = CH2

CH3 CH3
Isobutylene ­
(Terminal alkene)
+ CO2(g)
Line
water

Milky
8. (A)
CH3

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*
Cold dil KMnO4 H OH
Syn addition
H * OH
Cis
CH3
Erythro
Pos
Meso

9. (B)
CH2 = CH2
Na Metal
×
Na Metal 1
__
CH3 – C º CH CH3 – C º CNa + H (g)­
(acid- base) 2 2
Terminal alkyne 1 mole
__
1 mole
2

11.2 L gas

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ALLEN Hydrocarbon 3

10. (A)
R
Na / NH3
R–CºC–R Trans
Birch reduction
R
Lindlar's Catalyst R R
Cis

11. (C)
Alkene and Alkane comes out after first bottle (having ammonical CO2Cl2).
ammonical
HC º CH CuC º CCu ¯
Cu2Cl2
Terminal Alkyne Red ppt
12. (A)

O3/H2O
CH3– CH2 – C º CH
Terminal + Release CO2(g)
Alkyne KMnO4/H

NH4OH / Cu2Cl2
Red ppt
Br2 / CCl4
Product
with No ppt, No. Colour
change, No gas release.

While above 3 reagent neither release gas nor gives ppt respectively with non-terminal alkyne. So
First 3 reagent can be used to detect non-terminal of terminal alkyne (position of triple bond).
13. (C)
Alc. KOH
CH3– CH2 – C º CH CH3– C º C – CH3
Terminal Non-terminal
NaNH2
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Process happen via removal & re-addition of HÅ.

14. (A)
Alc. KOH
CH3– CH2 – C º CH CH3– C º C – CH3
Terminal Non-terminal
NaNH2

Process happen via removal & re-addition of HÅ.

15. (B)
% of iso-octane is called octane number Fuel with higher octane number / rating ; are considered
good for high performance of Engine.
16. (B)
17. (D)

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4 JEE-Chemistry ALLEN
By wurtz & kolbe's Electrolysis alkane (Open chain) having even N of carbon are prepared in better
yield.
18. (B)
C3H 8 + 5O 2 ¾¾
® 3CO2 + 4H 2O
1 Mole 5 Mole

19. (C)
7
C2H6 + O2 ¾® 2CO2 + 3H2O
2
7
1 mole mole
2
7
1 Lt. Lit
2
70
10 Lt. = 35 Lit O2 required.
2
ß
\ 35 × 5 Lt. (as only 20% O2 is in air)
Air needed = 175 Lit.
20. (B)
Add two –OH in syn addition way ; on less crowded side.
21. (A,B,C,D)
Wolf kishner, clemenson, Mozingo & red P + Hl Can do this reduction.
22. (A,B)
H2/Pt
CH2 = CH – CH = CH2 CH3 – CH = CH – CH3
(1 eq.)
Du = 2 (B)
(A)
(C4H6)
* Correction in Q. During A to B write '1 Equivalent' below arrow.

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23. (A,B,C)

Let : (A) is in Cis form.

A: But-2-ene (Cis)
Possible isomer of A.
O
P1 : Ozonolysis
2 CH3–C–H
O3 / Zn
(Trans) Ethanol
But-2-ene
[GI of A]

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ALLEN Hydrocarbon 5

P2 :

O
P3 : O3 / Zn
O + H–C–H
[C.I. of A] Propanone Methanol

24. (A,B,C,D)
3 4–
(A) Al + C Al (OH)3 + CH4
+ –
2+ H OH
(B) Ca (C º C ) Ca(OH)2 + CHºCH
+ –
2+ 3– – H OH
(C) Mg (C –C º C ) Mg(OH)2 + CH3CºCH
+
H
(D) Me3 C – H + KMnO4 Me3C – OH
D
25. (D)
Ammoniacal AgNO3
CH3CH2C º CH White ppt
Terminal Alkynes (Tollen's Test)

26. (A)®S ; (B)®R ; (C)®P ; (D)®R,S

O
C – CH3 CH2 – CH3
Zn(Hg), HCl
(A)
Cl Cl
Clemmensen reduction

Ans. (S)
O
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C – CH3 CH2 – CH3

(B) (1) NH2NH2
(2) OH–, D
HO HO

Wolf-Kishner reduction

Ans. (R)

Na, NH3
(C)

Birch Reduction
Ans. (P)

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6 JEE-Chemistry ALLEN

O
Zn(Hg), HCl
(D)

(i) NH2 NH2

–
(ii) OH , D

Ans. (R, S)

27. (A)®Q ; (B)®R ; (C)®S ; (D)®P

H2O
(A) RCOONa R–R
Electrolysis
Kolbe electrolysis (Q)
NaOH, CaO
(B) R–CH2–COOH R – CH3
D
Oakwood degradation / Sodaline process (R)
(i) AgNO3
(C) RCOOH (ii) Cl2D
R – Cl
Hundieker reaction (S)

(D) R¢ – X + R2Culi R–R

Correy – House Reaction (P)

28. (A)®Q ; (B)®P ; (C)®S ; (D)®R

CH3 CH3
H2, Pd-BaSO4
(A) CH3 – C º C – CH3 C=C
H H
Na / NH3(l)
CH3 H
(B) CH3 – C º C – CH3 C=C
H CH3
NaNH2, D
(C) CH3 – C º C – CH3 CH3CH2 – C º CH
Removal & readdition of Problems in Presence strong bases

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alc. KOH
(D) CH3– CH3–C º CH 2-Butyne
D

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ALLEN Hydrocarbon 1

EXERCISE # J-MAINS
1. (1)
H Br
Br2, hn
CH3 – CH – C – CH3 CH3 – C – CH2 – CH3
CH3 H CH3
Intermediate Þ Most stable carbon free radical

1° : 2° : 3° CH3 – C – CH2 – CH3

1 82 1600 CH3
2. (4)
R ¢ - X + R 2CuLi ¾¾
® R ¢ - R + RCu + LiX
Alkanes

3. (1)

KC Product Br
CH2 = C – CH – CH3 CH2 = CH – CH – CH3
Br
T.C. Product (40°C) CH2 – C = CH – CH3 Br
CH2 – CH = CH – CH3
H Br
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Thermodynamically
controlled conditions

4. (1)

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9.
8.
7.
6.
5.

(4)
(1)
(2)
(4)
(2)
JEE-Chemistry

H(1) is anti to Br.

(1)O
3

2 (2) ZnH O
CH3CH = CHCH3 ¾¾¾ ® 2CH3CHO
ALLEN
®

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ALLEN Hydrocarbon 3

10. (2)
Terminal alkynes can react with sodium in liquid ammonia.

So Ans is (2)
11. (4)

So Ans is (4)
12. (2)
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Trans (Major) (Ans. 2)

13. (4)
O
(1) O3
CH3–C=C–CH3 2 CH3–C–H
(2) Zn/H2O
H H
Molecular mass = 44 V
So Ans. is (4)

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4 JEE-Chemistry ALLEN
14. (4)
O O
ozonolysis
–CH=CH2 –C–H + H–C–H
vinyl group to meldehyde

So Ans is (4)
15. (4)

H
(1) O3
CH3–C = C – C – CH3 CH3–C=O
(2) Zn–H2O
CH3 H H CH3
Acetone
+
O
H3C
H
Propionaldehyde

16. (3)
CH3 H
Li/NH3
CH3–CºC–CH2–CH2–CH3 C=C
H CH2–CH2–CH3
So Ans. is (3)
17. (2)

O
CH=CH–C–CH3 NH NH CH=CH–CH2–CH3
2 2

OH–, D

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HO HO
Acid
sensitive

So we connect wolf-kishner reduction use Zn(Hg), HCl.

So Ans. is (2)
18. (1)

Cl Cl
D
CH3–C–Cl + 6Ag + Cl–C–CH 3 CH3–CºC–CH3
Cl Powder
Cl But-2-yne

19. (3)
Ca [C ºC]–2
+2

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ALLEN Hydrocarbon 5
20. (1)
B2H 6/THF
CH3–CH=CH 2 – CH3–CH2–CH2
H2O 2/OH
OH
Anti-Markowni kov addition of H2O
21. (2)
Polymerisation
nHCºCH —CH=CH— n
yne poly-yne
Poly-yne is obtained by polymerization of alkyne such as acetylene.

22. (2)

Dipotassium succinate
Anode

23. (4)
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24. (1)

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6 JEE-Chemistry ALLEN
25. (1)

CH3 CH3
Br2/hv
CH3–CH–CH 2–CH3 CH3–C–CH2–CH3
Br (Major product)
2-Bromo-2-methyl butane
CH3
Br-CH2–CH–CH2–CH3
CH3 Minor
CH3–CH–CH–CH3 products

Br
CH3
CH3–CH–CH2–CH2–Br

Relectivity ratio for bromination is

1° : 2° : 3° : : 1 : 82 : 1600
Hence 3° product will be major product.

26. (2)
One of the steps in endothermic in HCl & HI.

27. (4)

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28. (3)

a – b elimination (Renovel of HBr) Þ Resonance stabilized alkene

29. (2)

Intermediate – resonance stabilized carbon free radical

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34.
33.
32.
31.
30.

(2)
(4)
(1)
(1)
(1)
ALLEN
®

So Ans. is (4)
a-b elimination-2 times
Hydrocarbon
7
 8

37.
36.
35.

(1)
(2)
(3)

(ii)H 2O 2 ,OH - úû
(i)B2 H 6 ù
JEE-Chemistry

Þ Anti-Markovnikor addition of H2O without rearrangement

ALLEN
®

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ALLEN Hydrocarbon 9
38. (3)

39. (4)
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40. (3)

O O
Ozonolysis
HC º C – CH2 – CH3 H–C–C–CH2–CH3
Ammonical
Silver Nitrate
Silver Mirror
Due to aldehyde group

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ALLEN Hydrocarbon 1

EXERCISE # J-ADVANCED
1. (D)
CH3–CºCH ¾¾¾®
Tollen 's
Test
white ppt

CH3–CH=CH2 ¾¾
"
® No result
2. (A)
Let R : –CH3
® More Energy release faster & better product obtained.

ROR µ HOH Release

and we know HOH µ Unstability.

3. (C)
Because one of the step is endothermic in both case.
4. (B)
5. (B)

H2/Pd
BaSO4
POS
Optically Inactive

6. (B)
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7. (A)

p
H H
C C Molecular Plane is
Nodal Plane in ethene
H H
p

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2 JEE-Chemistry ALLEN
8. (D)

"
CH3 – C º C – CH3 No result
9. (A)

10. (B)

OH
+
H
–H2O + +
H H Trans Cis Butene

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Use Br2
TAE x
Trans Anti Enthro CAT
(Cis Anti Threo)
H Br
H Br
* Br
H Br
Br H Br
(1)
(2) (2)
Meso
Optically Optically
Active Active

11. (B)
Li NH3 react same as birch reduction.

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ALLEN Hydrocarbon 3
12. (A)

OH

Conc. H3PO4

Conc. H3PO4 Best for dehydration Reaction, Because with (HCl, ZnCl2), (Conc HCl), (Conc. HBr)
Substitution Reaction Take Place.
13. (B)

14. (D)

Br
2Na (eg.)
Wurtz Reaction

Cl

15. (A)
NOCl
CH3 – CH = CH2 CH3 – CH – CH 2
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Cl NO

Cl

NOCl NO+ + Cl– NO

+
NO
CH3–CH = CH 2 CH3–CH – CH2

Cl
NO
CH3–CH – CH2
Cl

16. (A) Correct option is A.

Addition of halogens on alkenes is predominantly anti-addition Anti addition of Br 2 on trans alkene
produces meso compound

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4 JEE-Chemistry ALLEN
17. (C)
CH 3 - CH 2 - CH 2 - CH 2 - CH 2 - CH 3
Hexane

CH3 CH 3
H3C–CH–CH2–CH2–CH3 H3C–C–CH2–CH3
2-Methyl Pentane 2, 2-dimethyl butane

H3C–CH2–CH–CH2–CH3 H 3C–CH–CH–CH 3
CH3 CH 3 CH3
3-Methyl Pentane 2,3-Dimethyl butane

18. (B)
Br alc. KOH NaNH2
CH2=CH–Br CHºCH
Br
19. (D)

NaNH2
CH3CH2CºC–H CH3CH2CºC Na

CH2–CH2–CH2–CH3
Br

CH3CH2CºC–CH2–CH2–CH2–CH3
3-Octyne

20 (B)

1
B.P. µ
Branching

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21. (A)
NaNH2
H (Base) C
Excess
HO O
CH2–CH2–I

C–CH2–CH3
O
CH3–I
H3CO
H2(Lindlar's Catalyst) CH2–CH3
H H H 3C–O
Cis alkene

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ALLEN Hydrocarbon 5
22. (C)

23. (B,D)

H Br H2, catalyst H Br
H2 C CH3

Optically inactive

Br H Br H
H2 C CH3 H2, catalyst

Optically inactive

24. (C)
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25. (D)

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6 JEE-Chemistry ALLEN

26. (D)

27. (4)

28. (A,B,D)

Sol. (A) ¾¾¾¾

ConcH 2SO 4
D
®

(B) ¾¾®
FeD

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(C) ¾¾¾¾®
(1)Br2 NaOH
(2)H OÅ ¾¾¾¾ ¾
(3)Soda lim e
®
3 D

(D) ¾¾¾¾
ZnHg,HCl
®

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ALLEN Hydrocarbon 7

29. (B,C)

(A) COONa + H2O

Electrolysis
Hexane

NaOH, CaCl
(B) COONa
Propane

Cl Zn, dil HCl

(C) (Reduction)
Propane

Br
(D) Br Zn
H3C Propane

30. (B,D)

Cl
Cl Cl
UU, 500K
(A) + Cl2(Excess)
Cl Cl
Cl

CH3 Br (i) Alc. KOH Red

(B) Br (ii) NaNH2 Hot
Iron tube
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Aromatic

Br O–Et
(C) OEt

H H
Na+
(D) Na OMe
Aromatic

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8 JEE-Chemistry ALLEN
31. (1.62)
Mg2C3 + 4H2O 2 Mg(OH)2 + CH3CºCH
NaNH2
CH3CºCH CH3–CºC Na
Å

(P)
Me – I
4 = .1 Mol.
__
40 CH3–CºC–CH3
(.075 m mol)

Red Hot
3 CH3–CºC–CH3 1 rum tube
873 K
1
__
.075 × .4 ×
3
= .01 Mol.
The value of x = 162 × 0.1 = 1.62 gm
32. (3.2)
O
2+ +
Hg H
(P) CH3–C–CH3 (.01 mol)
Kucherov
.1 mol Reaction
(Ba)OH2 &
aldol condensation
CH3
C = CH – C – CH3
CH3 O
NaOCl
80%
CH3

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C = CH – C – OH + CHCl3
CH3 O
80
.04 × ___ .032 mol
100
The value of Y = .032 × Mw = .032 × 100 = 3.2

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ALLEN Hydrocarbon 9
33. (12 or 8)

8 When oxygen is not considered

Or as sp2 hybridized

12 when oxygen in considered as sp2 hybridized.

34. (A) Most stability of radical, less is the bond Energy

H
(P) + H° 2° Carbon
Free Radical
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°
(Q) Ph - CH 2 - H ¾¾
® Ph - CH 2 + H °
Most Stable due toresoname

(R) CH 2 = CH - H ¾¾
® CH 2 = CH + H °
Less Stable

(S) CH º C – H ¾¾
® CH º C ° – H °
|
(SP )
More % S Character
decreases stability

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10 JEE-Chemistry ALLEN

35. (D)

Initiation step is endothermic hence option (A) is Wrong.

Propagation step involving °CH3 formation is endothermic hence option (B) is wrong.

Propagation step involving CH3Cl formation is exothermic hence option C is wrong.

Reaction

CH4 + Cl2 ¾® CH3–Cl + HCl

CH4 ¾® CH3° + H° DH = 105 KCal/mol

Cl2 ¾® Cl° + Cl° DH = 58 KCal/mol

Cl° + CH3° ¾® CH3–Cl DH = –85 KCal/mol

Cl° + H° ¾® HCl DH = –103 KCal/mol

CH4 + Cl2 ¾® CH3Cl + HCl DH = –25 Kcal/mol

Overall reaction is exothermic with DH° = – 25 Kcal/mol

Hence Option D is correct.

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