CPP - Hydrocarbon

NAME: _______________________ BATCH: _______________ DATE: ______________
CHAPTER PRACTICE PROBLEM

Subject: Chemistry Topic: Hydrocarbon
SECTION – A [+3, –1]

(Objective. Only one correct option)
1. Product of the following reaction will be:

H + H 2 
Pd

CH2
CH3
(a) Racemic mixture (b) Diastereomers
(c) Meso (d) Constitutional isomers
2. CH3
Br + Br2  
o
300 C
H
CH2
H2 C CH3
Which of the following compounds will not be obtained as a product in the above
reaction?
CH3
CH3 CH3 CH3
H Br
H Br H Br Br H
(a) (b) (c) CH2 (d)
Br H H Br H Br
H Br
H2C CH3 H2C CH3 H2C CH3
CH3
3. Which of the following compounds can be best prepared by Wurtz-reaction?
(a) Iso-butane (b) n-butane (c) n-pentane (d) Iso-pentane
4. Pure methane can be prepared by

(a) Wurtz reaction (b) Kolbe electrolysis method
(c) Soda-lime de-carboxylation (d) Reduction with H2
5. An alkane (mol. wt. = 86) on bromination gives only two monobromo derivatives
(excluding stereoisomers). The alkane is
CH3
H3C CH CH2 CH2 CH3
(a) (b) H3C C CH2 CH3
CH3
CH3
CH3
H3C CH CH CH3
(c) (d) H3C C CH3
CH3 CH3
CH3
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6. Among the following free radical bromination reactions, select those in which 2o
halide is the major product?
CH3
(P) 
Br2 / hv
 (Q)

Br2 / hv

H2C CH3
H3C CH3
(R) (S) 
Br2 / hv

Br2 / hv
CH3
(T) 
Br2 / hv
 (U) H3C CH3 
2
 Br / hv
(a) P, Q, R, S (b) P, R, U (c) P, R, S, T (d) P, Q, R, S, T
7. Product obtained in the following Wurtz reaction is

CH2 Cl

Na / (Dry ether)

H3C
H2 C Cl
CH3
(a) (b)
H3C CH3 H3C
(c) (d) Both (a) and (b)

H3C CH3
8. Which of the following bromides is the major product of the reaction shown below,
assuming that there are no carbocation rearrangement?
+ HBr (1 equivalent) 
 C13 H17 Br
Br
Br
(a) (b)
(c) (d)
Br
Br
9. Product of which of the following reactions, is racemic mixture?

CH3

H2
 
Br2

(a) Pt (b) CCl4
H3C CH3
CH3
CH3
H3C CH3
(c) 
H2
 (d) 
Br2

Pd CCl4
CH3
10. (R)-3-bromocyclopentene (shown below) reacts with Br2 / CCl4 to form two products,
Y and Z, Y is not optically active (does not rotate plane-polarized light). What is the
structure of Y?

Br2 / CCl4
 Y+Z
Br
Br Br Br
(a) (b) (c)
Br Br Br Br Br Br
Br
(d) (e)
Br Br Br
11. Product obtained in the following reactions (1), (2) and (3) is
O
Br
alc. KOH
Reaction (1) (A) (major)
alc. KOH
Reaction (2) (B) (major)
Br
O
alc. KOH
Reaction (3) (C) (major)
Br
(a) A = B but C is different (b) A = C, but B is different
(c) B = C, but A is different (d) A = B = C all products are identical
12. The product(s) of the following reaction can best be described as:
CH3
CH3
 
HBr

(a) a racemic mixture (b) a single enantiomer

(c) a pair of diasteriomers (d) an achiral molecule
13. Product obtained in given reactions (1), (2) and (3) is

Cl
Cl Cl
3 mole alc.KOH
Reaction (1) (A)
Cl Cl
Cl
Cl
Cl Cl
3 mole alc.KOH
Reaction (2) (B)
Cl Cl
Cl
Cl
Cl Cl
3 mole alc.KOH
Reaction (3) (C)
Cl Cl
Cl
(a) A = B, C is different (b) A = C, B is different
(c) B = C, A is different (d) A = B = C is same
14. 2,4-hexadiyne (C6H6) is allowed to react with Li in NH3 (liq). The product obtained
is treated with 1 equivalent of Cl2 in CCl4. Which of the following constitutional
isomers are possible products?
Cl Cl Cl
CH3 CH3 CH3
H3C H3C
Cl Cl Cl
(I) (II) (III)
Cl
Cl Cl CH3
H3C Cl
(IV) (V)
(a) I and II (b) II and III (c) I and V (d) I and III
15. In the following reactions, difference in reagents results in the different product
mixtures. Find relation between a and b.
H3C H3C
Case A + CH2N2 Heat (a) (major)

CH3
H3C
H3C H3C
Heat (b) (major)

Case B + CH2I2
Zn
CH3
H3C
(a) a  b (b) a  b (c) b  a (d) Cannot predict
16. Predict the product of the following reaction:

H3C CH3
H
A

CH3 CH3
(a) CH3 (b)

CH3
CH2 CH3
(c) (d)
CH3 CH3
17. In the following reaction, the product (A) is:
CH2
CH3 
HBr

 A (Major)
CCl 4
Br
Br CH3
CH3
CH3
(a) (b)
CH3 Br
CH3
CH3
(c) (d) CH3
CH3
Br
18. Find the product (A).

CH3
+ CBrCl3 
hv
 (A) (no ring substitution)
(a) Ph––CH2––Cl (b) Ph––CH2––Br

(c) Ph––CH2––CCl3 (d) Ph––CH2––CBrCl2
19. Trans – cyclohexane-1, 2-diol can be obtained by the reaction of cyclohexene with
(a) KMnO4 (b) OsO4
+
(c) Peroxy formic acid / H3O (d) SeO2
20. Which series of reactions will achieve the following transformation?

Br
H3C CH2 
1
 
2
 Cl
Cl
1 2 1 2
(a) Cl2 / CCl4 Br2 (b) HBr Cl2 / CCl4
(c) Cl2 / CCl4 NBS/hv (d) NBS / hv Cl2 / CCl4
21. The strongest electrophile of the following is:

(A) (B)
H3C CH2 NO2 CH2
(C) (D)
CH3O CH2 Cl CH2
22. Rank the following reactions A, B and C in order of increasing rate:
Me Me
(A) 
SO3 / H 2SO4

SO3H
Me Me
SO3H
(B) 
SO3 / H 2SO4

NO2 NO2
(C) 
SO3 / H 2SO4

SO3H
(a) B > A > C (b) B > C > A (c) A > B > C (d) A > C > B
23. Rank in order of increasing rate of reaction towards EAS with bromine in the
presence of FeBr2.
O O
O
(A) (B) (C)
O O O
(a) B < A < C (b) B < C < A (c) A < B < C (d) A < C < B
24. Product (B) in the given reaction is:


H
 (A) 
HNO3
 (B)
 
NO2
(a) (b) NO2
(c) (d)
NO2 NO2
25. In the following reaction, reactant A is
H3C CH3
+ A 
H 2SO4

H3C CH3
O CH3 H3C CH3 CH3
CO2H
(a) O (b) O (c) O (d)
CO2H
O CH3 H3C CH3 CH3
26. Which position will be attacked most rapidly by the nitronium ion (–NO2)+ when the
compound undergoes nitration with HNO3 / H2SO4?
A B C D
O
CH3
H3C
(a) A (b) B (c) C (d) D
27. All the hydrocarbons shown are very weak acids. One, however, is far more acidic
than the others. Which one is the strongest acid?
(a) (b) (c) (d)
28. Nitration takes place at the which position of the given compound?
CMe 3
D A
C
CHMe2
B
(a) A (b) B (c) C (d) D
29. In nitration of benzene by mixed acid the rate of reaction will be:
(a) C6H6 = C6D6 = C6T6 (b) C6H6 > C6D6 > C6T6
(c) C6H6 = C6D6 > C6T6 (d) C6H6 < C6D6 < C6T6
30. The product of the reaction

Cl
H D

Br2 / Fe

SiMe 3
is
Cl Cl
H Br H D
(a) (b)
Br
SiMe 3 SiMe 3
Cl Cl
Br D H D
(c) (d)
SiMe 3 Br
31. The major product of the reaction

O
C O

HNO3 + H 2SO 4

OMe
is
O O
C O C O
(a) (b)
O 2N
OMe NO2 OMe
O O
C O C O
NO2
(c) (d)
NO2
OMe OMe
32. There are three tribromobenzenes having M.P. 44oC, 87oC and 120oC. Which
statement is incorrect about these compounds?
(a) The highest melting isomer has most symmetrical structure
(b) The highest melting isomer has closest packing in solid state
(c) The highest melting isomer gives only one mononitration product
(d) 1,2,4-tribromobenzene should have melting point 120oC
SECTION – B [+4, –1]
(Objective. One or more than one correct option(s))
Cl2 / H2O
33. CH3  CH  CH2   Pr oducts
The product(s) (major as well as minor) of above reaction is/are (Do not consider
substitution products)
(A) CH3  CH  CH2 (B) CH3  CH  CH2
OH Cl Cl Cl
(C) CH3  CH  CH2 (D) CH3  CH  CH2
OH OH Cl OH
34.
Anhy.AlCl3
 ClCH 2 CH 2 Cl       
 Pr oducts
The product (s) (major as well as minor) of above reaction is/are
(A) (B)
CH2 CH2 CH2CH2Cl
(C) CH3 (D)

CH2Cl
CH
Cl
SECTION – D [+4, 0]
(Numerical / Integer type)
1. A polyene, on reductive ozonolysis, forms two moles of CH3CHO, two moles of

HCHO and one mole of the following compound.
OHC  CH  CHO
O  C  CHO
How many allylic hydrogen atoms are present in one molecule of the polyene?
2. CH3
BF3
CH3  CH  CH2  CH2  OH   Pr oducts
Heat
How many monochloro product(s) is/are formed, if Cl2 reacts with the major product
of above reaction in presence of sunlight? (Consider stereoisomerism)
MnO 
3.
Anhy.AlCl3 4 / OH
+ CH2Cl    X  
  Y
Heat
How many carbon atom(s) is/are present in one molecule of (Y)?
4. Compound (A), C7H15Cl, on treatment with alcoholic KOH forms three alkenes
(without considering stereoisomerism) having same molecular formula C7H14. On
reductive ozonolysis the alkenes produce the following compounds:
CH3CHO,CH3COCH3 ,CH3COCH2CH3, CH3COCH  CH3 ,HCHO and CH3CH2COCH  CH3
CH3 CH3
How many tertiary carbon atoms are present in one molecule of (A)?
5. One mole of hydrocarbon (A) reacts with 1 mole of bromine giving a dibromo
compound C5H10Br2. (A) on treatment with cold dilute alkaline KMnO4 solution forms
compound C5H12O2. On ozonolysis, (A) gives equimolar amounts of propanone and
ethanal. (A) on reduction gives alkane (B). Calculate the number of monochloro
derivatives possible for compound B.
6. Cl
CH CH2 CCl3
NaOH  excess  Sodalim e

  X    Y
 
How many oxygen atoms are present in one molecule of (Y)?
7. Cl
Anhy.AlCl3 KMnO 4 / KOH

+    X  
 Y

How many oxygen atoms are present in one molecule of the organic compound (Y)?
SECTION – E [+8, 0]
(Matrix Matching)
1. Match the compounds mentioned in Column – I with their properties mentioned in

Column – II
Column – I Column – II
(A)
(P) Decolorizes bromine water
(B)
Forms a 3o-chloride when reacts

(Q)
with HCl
(C)
Forms HOOC – COOH along with
(R) other products when reacts with
hot acidified KMnO4 solution
(D)
Undergoes aromatic electrophilic

(S)
substitution reactions
2. Match Column I with Column II:

Column I Column II
(A) (p) Aromatic
N
O
(B) (q) Non-aromatic
N S
(C) (r) Anti-aromatic
N
H
(D) NH2 (s) Satisfy the Huckel rule
N O
H
ANSWERS [Quiz: Hydrocarbon]
1. B 2. D 3. B 4. C
5. C 6. B 7. D 8. D
9. B 10. C 11. D 12. C
13. D 14. D 15. C 16. D
17. C 18. B 19. C 20. D
21. B 22. A 23. A 24. B
25. C 26. B 27. C 28. B
29. A 30. D 31. C 32. D
33. A, B, D 34. A, B, C
1. 7 2. 5 3. 7 4. 2
5. 4 6. 1 7. 2
1. (A) – (p, q, t); (B) – (p, q, s); (C) – (p, q, r, t); (D) – (s)
2. (A) – (p, s); (B) – (p, s); (C) – (q); (D) – (p, s)

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NAME: _______________________ BATCH: _______________ DATE: ______________

CHAPTER PRACTICE PROBLEM

SECTION – A [+3, –1]

1. Product of the following reaction will be:

4. Pure methane can be prepared by

(a) P, Q, R, S (b) P, R, U (c) P, R, S, T (d) P, Q, R, S, T

7. Product obtained in the following Wurtz reaction is

(c) (d) Both (a) and (b)

9. Product of which of the following reactions, is racemic mixture?

(a) a racemic mixture (b) a single enantiomer

13. Product obtained in given reactions (1), (2) and (3) is

Case A + CH2N2 Heat (a) (major)

Heat (b) (major)

16. Predict the product of the following reaction:

(a) CH3 (b)

18. Find the product (A).

(a) Ph––CH2––Cl (b) Ph––CH2––Br

20. Which series of reactions will achieve the following transformation?

21. The strongest electrophile of the following is:

24. Product (B) in the given reaction is:

(a) (b) NO2

O CH3 H3C CH3 CH3

(a) (b) (c) (d)

(a) A (b) B (c) C (d) D

30. The product of the reaction

31. The major product of the reaction

The product (s) (major as well as minor) of above reaction is/are

(C) CH3 (D)

1. A polyene, on reductive ozonolysis, forms two moles of CH3CHO, two moles of

CH3CHO,CH3COCH3 ,CH3COCH2CH3, CH3COCH  CH3 ,HCHO and CH3CH2COCH  CH3

NaOH  excess  Sodalim e

Anhy.AlCl3 KMnO 4 / KOH

1. Match the compounds mentioned in Column – I with their properties mentioned in

(P) Decolorizes bromine water

Forms a 3o-chloride when reacts

Undergoes aromatic electrophilic

2. Match Column I with Column II:

(C) (r) Anti-aromatic

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NAME: _______________ BATCH: _ DATE: ________