LPP - Hydrocarbon: Fiitjee

LPP - Hydrocarbon FIITJEE
Single Correct
Br
alc. KOH
 ( A)
H
1. D
(A) (B) No-reaction (C) H (D) None of these
Br Cl

 , OH HCl
 (A)   (B), B is
NMe3
2. +
Cl
Br Cl
(A) (B)
Cl Br Cl
Cl
Br Cl
(C) (D)
Br Cl OCl
CH3
Me3N 
OH
  Olefinic product

3. CH3
Et Et
(A) (B) (C) (D) None of these
C6H5
H3C H alcoholic KOH
 A
E2
Br H
4. C6H5
H3C C6H5 H3C C6H5

C C
(A) (B)
C C
H C6H5 H5C6 H
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H CH3
C
(C) (D) None is correct
C
H5C6 C6H5
Cl
H H
alc . KOH
D   A. The structure of 'A' is
D
5.
H D H D H H H D
(A) (B) (C) (D)
D D D D
6. What is/are the product(s) from the following reaction?
 Br2 / CCl4 
?
Br
(A) (B) (C) (D)

Br
Br Br Br Br Br
Br
7. Which of the following product is not formed in the following reaction?
 HBr 

Br
Br
Br
(A) (B) (C) (D) Br
8. What are the major organic products when following molecule is treated with ozone, and then with Zn/H2O?
CH2
O O
O
(A) (B)
,H C H , CO 2, H2O
COOH O
O
(C) (D)
, CH2O ,H C OH

O OH
KMnO4 H3C
Alkene (X) 

+ X is :
9. CH3 O
(A) (B)
(C) (D)
10. The major product of the following reaction is:
OH
( i ) H 3 PO4 , 200 C

( ii ) C6 H 5CO3 H

O OH
CHO
(A) O (B) (C) (D)
CHO
Multi Correct
Br2

CCl4
 Identify product's:
11.
Br Et
Br
Br
Et Br
(A) (B) (C) (D)
Et Br
Br
Br H
12. In which of the following reaction formation of racemic mixture occur/s?

Br2
(A) 
CCl4
 (B) Cold . KMnO4
 
CH3
H H
H  CH3
(C)  (D) H 
 

OH
OH
13. Which two of the following are most reactive toward bromination?
H3C
(A) (B) (C) (D)

Cold KMnO 4 (dil)
  Identify products:
14.
HO OH
(A) (B)
OH OH
OH OH
(C) (D)
OH OH
15. In which of the following reaction Diastereomer isomer will formed?

Cl
Cl

(A) O Et (B) 
E2 , t  BuO K





 
Cl
(C) (D) alc . KOH

NaNH 2  

 Cl 
Comprehension – 1
The halogens, Br2 and Cl2, add to alkenes. When the  electrons of the alkene approach a molecule of Br2 or
Cl2, one of the halogen atoms accepts them and releases the shared electrons to the other halogen atom. Therefore,
in an electrophilic addition reaction, Br2 behaves as if it were Br+ and Br–, and Cl2 behaves as if it were Cl+ and Cl–.
+
Br
H2C CH2 + Br Br  H2C

 CH2 + Br 
 BrCH2CH2Br
1,2-dibromoethane
a bromonium ion
a vicinal dibromide
Br2
16. cis  2  butene 
CCl4

How many products will obtain in this reaction?
(A) 1 (B) 2 (C) 3 (D) 4
I-Br
17. CH3  CH = CH 2   Product (A) is
Br I I Br
(A) (B) (C) (D)
I I Br Br
Br2
18.  x 
CCl4
( y ) products (including stereoisomer). Report sum of x + y (where x is the total number of
Isomer of
C4 H 8
alkene isomers and y is the total number of products produced).
(A) 8 (B) 9 (C) 10 (D) 11

Comprehension – 2
E2 reaction  Elimination bimolecular
In the general mechanism of the E2 reaction a strong base abstract a proton on a carbon atom adjacent to the one of
the leaving group. As the base abstracts a proton, a double bond forms and the leaving group leaves.
H CH3
H3C CH2 CH CH3  CH 3 ONa
 + +
CH 3OH
Br H3C H
(major)
Mechanism:

H CH3O H
CH3ONa + H3C CH CH CH3 

 H3C CH HC CH3 

Br Br   (trans-2-butene)
anti-coplanar transition state
(staggered conformation lower energy)
19. How many isomer of C4H9Br when reacts with NaNH2, diastereomers will form? (excluding stereoisomer of
alkyl halide)
(A) 0 (B) 1 (C) 2 (D) 3
20. Considering that

O Cl Cl
PCl5
  + POCl 3
C C
O Cl
PCl5 y NaNH 2 CH 3 I
     
O C C CH3
Report the value of y (in moles)
(A) 4 (B) 5 (C) 3 (D) 2
Integer Type
21.
O
Reaction-1: Ph C CH3 PCl5
 x NaNH 2
  CH 3 I
   Ph  C  C  CH 3
Br
Reaction-2: 2y NaNH
  CH 3  C  C  CH 3
Br
Reaction-3: Ph z NaNH 2
CH CH2  Et  I
   Ph  C  C  Et
Cl Cl
x, y, z are moles used
Sum of [x + y + z = ?]
O Cl Cl
PCl5
Note:   + POCl 3
C C
22. Why is the alkyl halide below not capable of undergoing an E2 reaction upon treatment with sodium ethoxide?
CH3
Br
CH3
–
(1) Br is too poor a leaving group
(2) the substance is too hindered
(3) too much angle strain would be present in the alkene product
(4) sodium ethoxide is a poor base to use in E2 reactions
(5) the C–H and C–Br bonds which need to break cannot achieve an anti-periplanar orientation
23.
Br
xNaNH 2 CH 3 I
Ph C CH3  ( A)   Ph  C  C  CH 3
Br
Br
y NaNH 2
 
Br
Sum of (x + y = ? )
24.
NaNH 2
Ph CH2 CH CH2 CH3  ( A)
Br
Total number of elimination product are (include stereoisomer and minor organic product also): ______
25. Identify the set of reagents / reaction conditions ‘X’ and ‘Y’ in the following set of transformation:
X Y
CH 3  CH 2  CH 2 Br   Product   H3C CH CH3
Br
(1) X = dilute aqueous NaOH, 20° ; Y = HBr / CH3COOH
(2) X = conc. alcoholic NaOH, 80° ; Y = HBr / CH3COOH
(3) X = dilute aqueous NaOH, 20° ; Y = Br2 / CHCl3
(4) X = conc. alcoholic NaOH, 80° ; Y = Br2 / CHCl3

Matrix
26.
Column-I (Compound) Column-II (No. of structural isomers

produced in  - E2 elimination )
(A) H3C P. Three
Br
H3C CH3 CH3

(B) Br Q. Zero
H3C CH3
CH3
(C) Br R. One
H3C
H3C CH3
CH3
(D) CH3 S. Two
H3C
Br
CH3

ANSWERS
LPP - Hydrocarbon
1. A
2. C
3. A
4. A
5. C
6. A
7. A
8. A
9. A
10. A
11. B,D
12. C
13. A,D
14. A,B
15. A,D
16. B
17. A
18. C
19. B
20. A
21. 8
22. 5
23. 5
24. 4
25. 2
26. A–S; B–R; C–P; D–Q


LPP - Hydrocarbon: Fiitjee

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(A) (B) No-reaction (C) H (D) None of these

H3C C6H5 H3C C6H5

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6. What is/are the product(s) from the following reaction?

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

7. Which of the following product is not formed in the following reaction?

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10. The major product of the following reaction is:

12. In which of the following reaction formation of racemic mixture occur/s?

FIITJEE Tower, C-56A/26, Institutional Area,Sec-62, Noida-201307. Ph: 0120-4754800/ 9599596524

15. In which of the following reaction Diastereomer isomer will formed?

(C) (D) alc . KOH

H2C CH2 + Br Br  H2C

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

alkene isomers and y is the total number of products produced).

(A) 8 (B) 9 (C) 10 (D) 11

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CH3ONa + H3C CH CH CH3 

anti-coplanar transition state

(staggered conformation lower energy)

20. Considering that

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Column-I (Compound) Column-II (No. of structural isomers

H3C CH3 CH3

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