Sri Chaitanya IIT Academy., India.

A.P, TELANGANA, KARNATAKA, TAMILNADU, MAHARASHTRA, DELHI, RANCHI

A right Choice for the Real Aspirant

ICON Central Office – Madhapur – Hyderabad
10. HYDROCARBONS
1. Given below are two statements: [22-01-2025, S-I]
Statement - I : One mole of propyne reacts with excess of sodium to liberate half a mole
of H 2 gas
Statement - II : four gm of propyne reacts with NaNH 2 to liberate NH 3 gas which
occupies 224mL at STP
In the light of the above statements, choose the most appropriate answer from the
options given below
1) Both Statement – I and Statement – II are correct.
2) Statement – I is incorrect but Statement – II is correct.
3) Statement – I is correct but Statement – II is incorrect.
4) Both Statement – I and Statement – II are incorrect.
Key: 3
1
CH 3  C  C  H  Na  H 3C  CNa   H 2
Sol: 2
CH 3  C  C  H  NaNH 2  CH 3  C  CNa   NH 3
Mwt:- 40g
1 mole  1 mole NH 3
0.1 mole  0.1 mole NH 3
0.1 mole NH 3  240 mL NH 3
Statement – I:- correct Statement – II:- NH 3
1( A) Given below are two statements.
Statement I: One mole of Ethyne reacts with excess of sodium to liberate half a mole
of H2 gas.
Statement –II : Four grams of propyne reacts with NaNH2 to liberate NH3 gas which
occupies 2240ml at STP.
In the light of the above statements, choose the most appropriate answer from the options
given below.
1) Both Statement-I and Statement-II are correct
2) Statement-I is incorrect but statement-II is correct
3) Statement-I is correct but Statement-II is incorrect
4) Both Statement-I and statement –II are in correct.
KEY: 2

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SOL:
  

H  C  C  H  2 Na  Na C  CNa  H 2

1mole 1mole

H 3 C  C  C  H  N aN H 2  H 3 C  C  C N a  N H 3

Pr opyne 1mole
40 g 22400 ml ( STP )

4g ?

 2240 ml  at STP 
1(B).
Given below are two statements.
Statement I: One mole of 1, 2-Dibromopropane on treatment with 3 moles of
NaNH2 followed by treatment with ethyl bromide gave 2 –pentyne.
Statement II: One mole of 1, 2-Dibromo ethane on treatment with ‘4’ moles of
NaNH2 followed by treatment with methyl bromide gave a 2-butyne.
1) Both Statement-I and Statement-II are correct
2) Statement-I is incorrect but statement-II is correct
3) Statement-I is correct but Statement-II is incorrect
4) Both Statement-I and statement –II are in correct.
KEY: 1
SOL :
Br Br
| |
3NaNH 2   C2 H 5 Br
H  C  C  CH 3 Na C  C  CH 3 C2 H 5  C  C  CH 3
| |
H H 2  Pent y ne

Br Br
| | 4 N aN H 2     2CH 3 Br
H  C C H Na C  C Na CH 3  C  C  CH 3
| |
H H 2  butyne

Both Statement-I and Statement-II are correct

2. The alkane from below having two secondary hydrogens is : [22-01-2025, S-II]
1) 2,2,4,4 –Tetramethylhexane 2) 2,2,4,5 –Tetramethylheptane
3) 4 –Ethyl -3,4 –dimethylocatane 4) 2,2,3,3 – Tetramethylpentane
Ans: 4
Sol:
Alkane
20 H

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1 10
20
20

2 4

20
20

3 2

20
20
20 20
20
4 4
20

2(a) In the following molecules how many carbon atoms arrange linearly:

CH 2  CH  C  C  CH 2  CH  CH 3

CH 3

1) 2 2) 3 3) 4 4) 5
Ans: 3
Sol: The carbon atoms which are directly attached with sp hybridised carbon atoms arrange
linearly.

H C  C  C  CH 2
1 2 3 4

2(b) Propargylic alcohol has sum of no of  ,  bonds & l.p:

CH  C- CH2 - OH

1) 10 2) 12 3) 11 4) 13
Ans: 3
Sol: No of   bonds  7
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No. of   bonds  2
No. of l. p  2
Total sum: 11

3. Match the LIST-I with LIST-I [23-01-2025 S-1]

List-I (Name of the Reaction) List-II (Product obtainable)

A) Swarts reaction I. Ethyl benzene

B) Sandmeyer’s reaction II. Ethyl iodide

C) Wurtz fitting reaction III. Cyanobenzene

D) Finkelstein reaction IV. Ethyl fluoride

Choose the correct answer from the options given below:

1) A-IV,B-I,C-III,D-II 2) A-IV,B-III,C-I,D-II

3) A-II,B-I,C-III,D-IV 4) A-II,B-III,C-I,D-IV

Key:2

Sol : Conceptual

3A. Match the List-I with List-II.

List-I (Name of the Reaction) List-II (Reagent used)

A) Finkelstein reaction I. Hg 2 F2

B) Sandmeyer’s reaction II. NaI / Acetone

C) Swarts reaction III. Cu2 X 2 / Hx

D) Wurtz fitting reaction IV. Na – dry ether

1) A- II, B-I,C-III,D-IV 2) A-II,B-III, C-I,D-IV

3) A-I,B-II,C-III, D-IV 4) A-III,B-II,C-I, D-IV
Key : (2)
Sol: Conceptual

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4. The product (A) formed in the following reaction sequence is [24-01-2025 S-I]

Key: 4
Solution:

2 
4. (a). ph  C  CH 
Hg , H 2 SO4
 A 
HCN
 B 
H 3O

 C , correct about product ‘C is
14
1)gives +ve test with NaH C O3 and liberates CO2 gas
2)gives an addition reaction with HBr
3)undergoes E1 elimination with concentrated H 2 SO4
4) Gives a diol with LiAl H 4
Key:2
Solution:
O OH
2 
ph  C  CH  Hg
 
, H 2 SO 4
 ph  C  CH 3  HCN
  ph  C  CH 3  H
3O


 ph  C  CH 2

CN COOH
5. Following are the four molecules P, Q, R and S. Which one among the four molecules will
react with H  Br aq at the fastest rate? [24-01-2025 S-I]

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Stable. Carbocation due to + M (electrophilic additional mechanism)

5 (a).Correct order of reactivity of the following P,Q,R,S with HBr is

H H
H
H
O N N O

(P) (Q) (R) (S)

1)P > S > Q > R 2) Q > R > P > S 3) Q > P > R > S 4) P > Q > S > R
Key:3
Solution:
H H H
H

N O N O

> > >

more Less + m less-I more-I
+ m power power power power
6. Identify product [A], [B] and [C] in the following reaction sequence.
CH 3  C CH   A 
 ii  Zn , H 2O   B   C 
 3
Pd / c i O
H2
[28-01-25 S-2]
1)  A : CH3CH2CH3 ,  B : CH3CHO, C  : HCHO

2)
 A : CH3  CH CH 2 ,  B : CH 3CHO, C  : HCHO

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o
2CH CH 2,  B  : H C  C  CH , C  : HCHO
3 3
3)
4) CH3-CH=CH2, [B] : CH3CHO, [C] : CH3CH2OH
ANS: 2
SOL:

6(i) The end product in the following sequence of reaction is

O 
CH   A  B 
1% HgSO CH MgX
HC 4
20% H 2 SO4
3

1) Acetone 2) Isopropyl alcohol

3) Acetic acid 4) Ethanol
ANS: 1
6(ii) Product of the following reaction,
 3
Me2C  CHCH 3 
ii CH3  S 
i O
2

1) Me2CO  CH 3CHO 2) CH3CHO  CH3COOH

3) Me2CO  CH 3COOH 4) 2Me2CO
ANS: 1
6(iii) End product in the following sequence of reaction is
Ca  OH 
 NH 2  NH 2

O3 / H 2O

2
   
OH  / glycol


1) 2) 3) 4)

ANS: 2
7. The product B formed in the following reaction sequence is: [28-01-25, S-2]

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ANS: 2
SOL:

7 (i)

Br KOH  alc 

 major product “P” product P is

ANS: 4
7(ii)
Cl
CH 3
 NaOH 
H 2O


Major product “A” consider the above chemical reaction. Product “A” is:

ANS: 4
7(iii) Identify the major product in the following reaction.

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Br
OH
C2 H 5OH
 major product
CH 3

ANS: 2
8. The major product of the following reaction is: [28-01-2025 , S-2]

1) 2-Phenylhepta-2,4-diene 2) 2-Phenylhepta-2,5-diene
3) 6-Phenylhepta-3,5-diene 4) 6-Phenylhepta-2,4-diene
ANS: 1
SOL:

It’s an E2 reaction and more stable conjugated alkane will be major product.
8(i) Identify the major product A and B respectively in the following set of reactions

ANS: 3

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9. In the following substitution reaction: [29-01-2025 S- I]

Product ’P’ formed is :

Key: 3

Sol: In SnAr , Leaving group para to electron withdrawing group is more prone for substitution

9(a). In the following substitution reaction:

Product ’P’ formed is :

Key: 3

Sol: In Aryl halides leaving group present at para position to the electron with drawing group
like - NO2 more favour for nucleophilic substitution

9(b). In the following substitution reaction:

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Key: 2

Sol: In Aryl halides leaving group present at para position to the electron with drawing group
like - NO2 more favour for nucleophilic substitution.

10. Which one of the following reaction sequences will give an azo dye ?
[29-01-2025 S-2]

Ans. (1)

10a) Which one of the following reaction sequences will give an azodye with 12 degree of
unsaturation.

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NO2 NO2
i ) Sn / HCl i ) Fe / HCl

 ii ) NaNO2 / HCl
iii ) Phenol , NaOH

ii ) NaNO2 / HCl
iii ) Aniline , HCl

1) 2)

NO2 NO2
i ) Sn / HCl i ) Sn / HCl

 ii ) NaNO2 / HCl

iii ) p Toluidine , HCl
ii ) NaNO2 / HCl /0  50 C


iii )   Napthol , NaOH
3) 4)

Key : 4
Sol :
N 2 Cl 
NO2 NH 2
 Sn / HCl

NaNO2 / HCl
0 50 C

NN +
OH   Napthol NaOH

 azodye 
Degree of unsaturation = 12

10b) Which one of the following reaction sequence will give orange colour azodye
NO2 NO2
 
i ) Sn / HCl i ) Sn / HCl
ii ) NaNO2  HCl , 0  50 C


iii )   Napthol , NaOH
ii ) NaNO  HCl , 0 50 C
2
iii ) Aniline
1) 2)
SO3 H
CN
 i ) H 2O

 i ) LiAlH 4
ii ) NaNO2  HCl
 ii ) HNO3  H 2 SO4
iii ) Sn  HCl
iii ) Aniline iv ) LAH
3) 4)
Key : 1
Sol :
NO2 NH 2
 Sn / HCl

NaNO2 / HCl

OH
N 2 Cl 

Orange colour
azo-dye 
NaOH


11. Given below are two statements :

Statement (I) : On nitration of m-xylene with HNO3, H2SO4 followed by oxidation,

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4-nitrobenzene-1, 3-dicarboxylic acid is obtained as the major product.

Statement (II) : CH3 group is o/p-directing while-

NO2 group is m-directing group.
In the light of the above statements, choose the correct answer from the options given
below : [29-01-2025 S-2]
(1) Both Statement I and Statement II are false
(2) Statement I is false but Statement II is true
(3) Both Statement I and Statement II are true
(4) Statement I is true but Statement II is false
Ans. (3)
Sol. Statement-I

Statement-II
–CH3 group is o/p directing while –NO2 group is meta directing.
11a) Given below are two statements :
Statement (I) : On di nitration of m – xylene with HNO3 and H 2 SO4 followed by oxidation
and followed by decarboxylation with soda lime, m – dinitro benzene is obtained as
major product.
Statement (II) : CH 3 group is meta directing group and ring activating group while NO2
group is O / P directing group and ring deactivating group.
(1) Both Statement I and Statement II are false
(2) Statement I is false but Statement II is true
(3) Both Statement I and Statement II are true
(4) Statement I is true but Statement II is false
Key : 4
Sol :

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CH 3 CH 3 CH 3 COOH
NO2 NO2
3  H 2 SO 4
 HNO
   HNO3  H 2 SO4
  
oxidation

CH 3 CH 3 CH 3 COOH
NO2 NO2 NO2
M - xylene

NaOH  Cao

NO2

NO2
Meta - dinitro benzene

11b) Given below are two statements :

Statement (I) : On nitration of toluene with HNO3 and H 2 SO4 followed by reduction with
m – toluidine will be formed as major product.
Sn / HCl ,
Statement (II) : m – toluidine is prepared by gabriel phthalamide synthesis from P –
chloro toluidine.
(1) Both Statement I and Statement II are false
(2) Statement I is false but Statement II is true
(3) Statement I is true but Statement II is false
(4) Both Statement I and Statement II are true
Key : 2
Sol :
CH 3 CH 3 CH 3

3  H 2 SO 4
 HNO
    
 Sn HCl
 P  Toluidine
Gabriel phthalamide
NO2 NH 2

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O O

CH 3 Cl + N-K N CH 3

O O
NaOH

ONa + H N CH 3
2
ONa

O P  Toluidine

12. Which among the following halides will generate the most stable carbocation in
Nucleophillic substitution reaction ? [29-01-2025 S-2]

12a) Which among the following halides will generate the most stable carbocation in
nucleophilic substitution reaction ?
Br
Br Br
Br
OCH 3
1) 2) 3) 4)

Key : 2
Sol : Carbocation is better stabilized by OCH 3 by mesomeric effect, in which all atoms posses
octet configuration.
12b) Which among the following halides will generate the most stable carbocation in
nucleophilic substitution reaction ?
Br Cl I I
1) 2) 3) 4)

Key : 3
Sol : Iodide is a better leaving group. Order of leaving groups is I  Br  Cl  F

13. Isomeric hydrocarbons negative Baeyer’s test (Molecular formula C9H12)

The total number of isomers from above with four different non-aliphatic substitution
sites is - [29-01-2025 S-2]
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Ans. (2)

13a) A mono substituted alkyl hydrocarbon ( X ) of the formula C10 H14

i) Does not decolourlise, cold dilute alkaline potassium permanganate solution
ii) It resists vigorous oxidation to give an aryl carboxylic acid
The total number of isomers possible for (X) with the above conditions is ________
Key : 1
Sol :
R C  CH 3 3
; R is C4 H 9 

13b) The total number of isomers of ‘X’ which give negative Baeyer’s test but undergo
oxidation to give
an aromatic acid is_______ ( Including stereo isomers)
Key : 4

Sol : i) ii) iii)

Above two isomers of C9H12 have four different sites for aromatic electrophilic
substitution reaction.

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