CPP FIITJEE HYDROCARBON

Part – A

1. O

O Cl2  excess 
  Disubstituted product
Fe

The major disubstituted product formed in the above reaction is

Cl O
Cl O
O
(A) O (B)

Cl
Cl
O
O
Cl
Cl O
(C) O (D)

Cl
Cl

2.
Hg  OAC 2 ,H2O
  Product
NaBH4
The product formed in the above reaction is
OH
(A) (B)
OH

(C) OH (D) Both A and B

3. How many chain isomers of C4H9 Cl can form only one type of alkene when undergoes
dehydrohalogenation reaction with alcoholic KOH?
(A) 2 (B) 3
(C) 4 (D) 5

4. HOOC CH2 CH2 CH2 CH2 CH2 COOH

KOH  excess  Electrolysis

   X   Pr oducts
 excess 
How many cyclic products are obtained in the above reaction?
(A) 1 (B) 2
(C) 3 (D) 4
5. H 4

H H
1 H 3
2
What is the decreasing order of reactivity of the above mentioned hydrogen atoms towards a
strong base which forms carbanions after removal of the hydrogen atoms?
(A) 1 > 2 > 3 > 4 (B) 2 > 1 > 3 > 4
(C) 1 > 3 > 2 > 4 (D) 2 > 3 > 1 > 4

6. Which of the following compounds exhibits three geometrical isomers?

(A) CH3  CH  CH  CH2  CH2  CH  CH  C2H5
(B) C2H5  CH  CH  CH2  CH2  CH  CH  C2H5
(C) CH2  CH  CH2  CH2  CH2  CH2  CH  CH2
(D) C2H5  CH2  CH  CH  CH2  CH  CH  CH2  CH3

7. t  BuOK CH3OK
Y   CH3 CH2 CHCH3    X
Major product  
Major product
Cl
Product [X] and [Y] formed in the above reaction are respectively
(A) CH3CH2CH  CH2 and CH3CH  CHCH3
(B) CH3CH  CHCH3 and CH3CH2CH  CH2
(C) CH2  CH  CH  CH2 and CH3CH2CH  CH2
(D) CH3CH  CHCH3 and CH2  CH  CH  CH2

8. Which of the following free radicals is stabilized by resonance?

(A) (B)

(C) (D)

9. Cl
1 eq.Mg/ether CH3C CD
[A] ; identify [A]:
Br
Cl D
(A)
(B)
D Br
D
(C) (D) none

D
10. Which of the following shows maximum enol content
 (A)
(B)
O O

(C)
O (D) O

11. Which of the following is most reactive towards electrophile attack:

(A) CH3CH = CH2 (B) CH2 = CH2
H3C
(C) (D) CH3CH2CH CH2
C CH2

H3C

dil.H2SO4
12. CH3 – CH = CH2
This reaction gives
(A) 1-propanol as a major product
(B) 2 propanol as a major product
(C) poly Isopropylene a major product
(D) isopropyl hydrogen sulphate as a major product

13. Which of the following reaction will yield 2, 2-dibromopropone ?

CCl 4
(A) HC  CH + 2HBr  (B) CH3 – CH = CH2 + Br2  
(C) CH3 – C  CH + 2HBr  (D) CH3 – CH = CH2 + HBr 

14. Which of the following does not exhibit tautomerism

(A) (B)
O O

(C) (D) none of these

O

15. How many number of optically active isomers are possible for 2, 3-dibromo butandioic acid
(A) 2 (B) 3
(C) 4 (D) 1

16.
OH MgBr
[X]; X is :
+
Br
(A). (B).

OH

(C). (D).
17. A hydrocarbon with formula C8H18 gives one monochloroderivative. The hydrocarbon is
(A) n- octane (B) 2- Methylheptane
(C) 2,2,4- Trimethylpentane (D) 2,2,3,3 – Tetramethylbutane

18. Which among the following compounds will undergo dehydration rapidly?
CH3
OH

(A) H3C OH (B)

CH3

CH3
(D)
CH3 OH
(C) H3C OH
H

19. HCl
CH3CH CH CH2 CH3 [A]
peroxide

HCl
[B]
Which of the following true for [A] and [B]:
(A) [A] and [B] are same (B) [A] and [B] are functional group isomer
(C) [A] and [B] are positional isomers (D) none

20. Consider the acid-catalyzed dehydration of the following compound.

CH3 OH
2 4 H SO
CH3CH CHCH2CHO  
heat
The major product obtained in the reaction is
CH3 CH3
(A) (B)
CH3 C CHCH2CHO CH3 CHCH CHCHO
CH3 CH3
(C) (D)
CH2 CCH2CH2CHO CH3CH CCH2CHO

21. meso-2, 3-dibromobutane on reaction with zinc produces mainly

(A) cis-2-butene (B) 1-butene
(C) trans-2-butene (D) 1, 3-butadiene

22. (CH3)3CMgCl on reaction with D2O produces

(A) (CH3)3 CD (B) (CH3)3COD
(C) (CD3)3 CD (D) (CD3)3COD
23. Propane can be best prepared by the reaction
2 Et O
(A) CH3CH2I  CH3I  Na 
2 H O
(B) CH3CH2COONa  CH3 COONa 

electrolysis
2 Et O
(C) CH3CH2Br   CH3 2 CuLi 
(D) None of the above

24. The number of possible structural isomers of an alkane containing six carbon atoms is
(A) 3 (B) 4 (C) 5 (D) 6
25. The reaction of 1-bromo-3-chlorocyclobutane with metallic sodium in dioxane gives
(A) Cl Cl (B) Cl Br

(C) Br Br (D)

26. Monochlorination of monodeuterioethane (CH3CH2D) yields

(A) chloroethane only
(B) monodeuteriochloroethane
(C) equal amounts of (A) and (B)
(D) a large amount of (B) and a small amount of (A)

27. The order of stability of the following alkenes is

(A) CH3 CH3 CH3 CH3 CH3 H
CH3CH CH < C C < C C < C C
H H CH3 CH3 H CH3
(B) CH3 CH3 CH3 H CH 3 CH3
CH3CH CH 2 < C C < C C < C C
H H H CH3 CH 3 CH3
(C) CH3 CH3 CH3 H CH3 CH3
C C < C C < C C < CH3CH CH2
CH3 CH3 H CH3 H H
(D) CH3 CH3 CH3 CH3 CH3 H
C C < CH3CH CH2 < C C < C C
H H CH3 CH3 H CH3

28. Which of the following reactions will lead to the creation of two chiral centres in the product?
4 CCl 4 CCl
(A) CH3CH  CHCH3  Br2   (B) CH3CH2CH  CH2  Br2  
(C) CH3CH  CHCH3  HBr  (D) CH3CH2CH  CH2  HBr 

29. trans-2-Butene on reaction with Br2 in CCl4 forms

(A) ()–2, 3-dibromobutane (B) meso–2, 3-dibromobutane
(C) an equimolar mixture of (A) and (B) (D) 1, 4-dibromo-2-butene

30. 1-Methylcyclohexene is allowed to react with B2H6. The product is then treated with H2O2
and NaOH. The reaction is
1.B 2H6
 

2.H2O2 / OH

CH3
The product formed is
(A) 1-methylcyclohexanol (B) 2-methylcycloheanol
(C) () trans-2-methylcyclohexanol (D) () cis-2-methylcyclohexanol

31. Anti-Markownikov’s addition of HBr is not observed in

(A) Propene (B) But-1-ene (C) But-2-ene (D) Pent-2-ene

32. The highest boiling point is expected for

(A) Isooctane (B) n-octane
(C) 2,2,3,3 – Tetramethylbutane (D) n-Butane

33. The reaction condition leading to the best yield of C2H5Cl are
 UV light dark
(A) C2H6(excess) + Cl2   (B) C2H6 + Cl2  
room temperatur e
UV light UV light
(C) C2H6 + Cl2(excess)   (D) C2H6 + Cl2  

34. The intermediate during the addition of HCl to propene in the presence of peroxide is
 
(A) CH3 CHCH2Cl (B) CH3 C HCH3
 
(C) CH3CH2 CH2 (D) CH3CH2 C H2

35. Complete the reaction :

CH3
(i) B 2H6
CH3 CH CH2 ?
(ii) H2O 2/OH
CH3
(A) Me3C.CH2CH2OH (B) Me3C.CH2(OH)CH3
CH3

(C) CH3 CH CH3 (D) None

OH CH3

36. State the major product of the following reaction

Br

CH 2 C CH3 OH

CH3

(A) OH (B) OH

CH 2 C CH3 CH CH CH3

CH3 CH 3

(C) (D)
CH 2 C CH 2 CH C CH3
CH 3 CH3

37. Which of the following elimination reactions follow the saytzev rule regarding regioselection
of the alkene products?
heat CH3CH2 Et3N
CH CH3 
CH3CH2CHCH3   
(A) (B)
NMe 3OH Me2SO
C2H5ONa H2SO4
CH3CH2CHCH3   CH3 CH CH3  
(C) EtOH (D) heat
Br OH

38. Consider the acid-catalyzed dehydration of the following compound.

CH3 OH
2 4 H SO
CH3CH CHCH2CHO  
heat
The major product obtained in the reaction is
CH3 CH3
(A) (B)
CH3 C CHCH2CHO CH3 CHCH CHCHO
CH3 CH3
(C) (D)
CH2 CCH2CH2CHO CH3CH CCH2CHO

Part – B
1. Saturated hydrocarbons generally undergo
(A) electrophilic addition reactions (B) nucleophilic substitution reactions
(C) nucleophilic addition reactions (D) free radical substitution reactions

ether
2. CH3Cl  Na  CH3Cl  Product
Which of the following is not a property of the organic product of above reaction?
(A) It is a saturated hydrocarbon
(B) It is formed by hydrogenation reaction of ethyne
(C) On combustion it produces CO2 and H2O
(D) It reacts with HCl in presence of CCl4

3.
COONa
Kolbe's electrolysis
COONa  Product

The major product of above reaction is:

(A) (B)

(C) (D)

4. Which of the following substance cannot decolourize bromine water?

(A) CH3CH2CH3 (B) CH3CH = CH2
(C) CH3 – C  CH (D) CH2 = CH2

5. CH3CH2CHCH3
AlC.KOH
  Product


Cl
Which of the following is not a product of above reaction?
(A) 1 – butene (B) Cis – 2 – butene
(C) Trans – 2 – butene (D) 1 – butyne

6. Which of the following reagent can be used to distinguish between CH3C  CCH3 and
CH3CH2C  CH?
(A) Br2/H2O (B) KMnO4/H+/
(C) KMnO4/OH–/Cold (D) AgNO3/NH4OH

7. Which of the following reagent can convert the following optically active compound to
optically inactive compound?
CH3

CH2  CH  C  CH2CH2Br
H
(A) HBr (B) HBr/peroxide
(C) NBS/h (D) Br2/h

8. Which of the following compound on reductive ozonolysis forms only CH3CHO?

(A) CH3CH2CH = CH2 (B) CH3CH = CHCH3
(C) CH3CH2CH = CHCH3 (D) CH3CH2CH = CHCH2CH3

9. Which of the following alkene is most reactive towards H2 gas in presence of metal catalysts?
 (A) CH2 = CH – CH = CH2 (B) CH3CH = CH2
(C) CH3CH = CHCH3 (D) (CH3)2C = C(CH3)2

10. Which of the following cyclic hydrocarbon can form maximum number of monosubstituted
products?

(A) (B)

(C) (D)

3  Na/NH 
11. CH3  C  C  CH3  Product
The organic product of above reaction is:
H CH3 CH3 CH3
(A) C C (B) C C
CH3 H H H
(C) CH3CH2CH2CH3 (D) CH2 = CH – CH = CH2

KMnO4 /H NaOH NaOH/ CaO
12. CH3CH  CHCH3 
 P  
   Q  

 R 
Product(R) in the above reaction is:
(A) C2H6 (B) CH4
(C) C2H4 (D) C2H2

13. Which of the following alkyne on acidified hydrolysis in presence of HgSO4 forms an
aldehyde?
(A) HC  CH (B) CH3C  CH
(C) CH3C  CCH3 (D) CH3CH2C  CH

14.

Hg CH COO  ,H O
3

NaBH4
2 2
 Product

The product of above reaction is/are

OH
OH
(A) (B)

OH
O
(C) (D)

15. Which of the following alkene is most reactive towards HCl?

 CH3
CH3 CH2 CHCH2 CH  CHCH3
(A) CH3  CCH2CH  CH2 (B)
CH3
CH3

CH3C  CHCH2CH3
(C) (D) CH3CH2CH2CH2CH = CH2
CH3
NaNH2
16. CH3 C  CCH2 CH2 CH3   CH3 CH2 CH2 CH2 C  CNa
How many moles of NaNH2 is/are needed in the above reaction?
(A) 3 (B) 7
(C) 4 (D) 5

17. H2 O
CH3  C  CH2   Product
H

CH3
The major product of above reaction is:
OH
CH3  CH  CH2OH
(A) (B) CH3  C  CH3
CH3
CH3
CH3  CH  CHO CH3  CH  O  CH3
(C) (D)
CH3 CH3

18. Which of the following alkene forms a meso product when reacts with Br2 in presence of
CCl4?

H CH3 CH3 CH3

(A) C C (B) C C
H3C H H H

CH3 CH3 CH3 CH3

(C) C C (D) C C
H CH3 CH3 CH3

19.

How many maximum number of product(s) is/are formed when the above compound
undergoes reductive ozonolysis at room temperature?
(A) 6 (B) 3
(C) 4 (D) 5

20. CH3

CH3  CH  CH  C  CH  CH  CH2  CH3

CH2  CH  CH  CH3
How many allylic hydrogen atom(s) is/are present in the above compound?
 (A) 12 (B) 8
(C) 10 (D) 9

21. The compound with highest boiling point is

(A) n-hexane (B) n-pentane
(C) 2, 2-dimethyl propane (D) 2-methylbutane

22. The treatment of C2H5MgI with water produces

(A) Methane (B) Ethane
(C) Ethanal (D) Ethanol

23. The order of reactivity of halogens towards halogenation of alkanes is

(A) F2 > Br2 > Cl2 (B) F2 > Cl2 > Br2
(C) Cl2 > F2 > Br2 (D) Cl2 > Br2 > F2

24. The chlorination of alkane involves

(A) Cl free radicals (B) Cl+ species
(C) Cl– species (D) CH3 free radicals

25. The reactivity of hydrogen atom in an alkane towards substitution by bromine atom is
(A) 1°H > 2°H > 3°H (B) 1°H < 2°H < 3°H
(C) 1°H > 2°H < 3°H (D) 1°H < 2°H > 3°H
light Na /ether
26. C5 H12  Cl2   C5 H11Cl   C
A  B

Only one structure of B is possible (A), (B) and (C) are

CH3 CH3 CH3 CH3
| | | |
(A) CH3 – C – CH3 CH3 – C – CH2Cl CH2 – C – CH2 – CH2 – C – CH3
| | | |
CH3 CH3 CH3 CH3
CH3 CH3 CH3 CH3
| | | |
(B) CH3 – CH – CH2CH3 CH3 – C – CH2CH3 CH3 – CH2 – C – C – CH2CH3
| | |
Cl CH3 CH3
(C) both are correct
(D) none is correct
H 2 / Pt O3 / H 2 O
27. CH2 = CH – CH = CH2   A  B
1 equiv.

A and B are
(A) CH3 – CH2 – CH = CH2, (CH3CH2COOH + CO2)
(B) CH3 – CH = CH – CH3, CH3COOH (2 mol)
(C) CH3 – CH = CH – CH3, CH3CHO (2 mol)
(D) CH3 – CH2 – CH = CH2, (CH3CH2CHO + HCHO)

28. CH3 – CH – CH = CH2 + HBr  A (predominant), A is

|
CH3
(A) CH3 – CH – CH – CH3 (B) CH3 – CH – CH2 – CH2Br
| | |
CH3 Br CH3
 (C) Br (D) None is correct
|
CH3 – C – CH2 – CH3
|
CH3

29. Stability of CH3 – CH = CH2 CH3 – C = C – CH3

(I) | |
CH3 CH3
(II)
CH3 – C = CH2 CH3 – C = CH—CH3
| |
CH3 CH3
(III)
(IV)
In the increasing order is
(A) I  III  IV  II (B) I  II  III  IV
(C) IV  III  II  I (D) II  III  IV = I

30. CH3
|
H–C
alkaline KMnO 4
||     A
H–C
|
CH3
Which is true about this reaction?
(A) A is meso 1, 2-butan-di-ol formed by syn addition
(B) A is meso 1, 2-butan-di-ol fomred by anti addition
(C) A is a racemic mixture of d and l, 1, 2-butan-di-ol formed by anti addition
(D) A is a racemic mixture of d and l 1, 2-butan-di-ol formed by syn addition.

Part – C

1. 1-Butene will exhibit

(A) geometrical isomerism (B) optical isomerism
(C) both (D) none of these

2. Ethylene can be prepared by electrolysis of an aqueous solution of

(A) Sodium acetate (B) Sodium succinate
(C) Sodium fumarate (D) Sodium propionate

3. 10 ml of a certain hydrocarbon require 25 ml of oxygen for complete combustion and the

volume of CO2 produced is 20 ml. What is the formula of hydrocarbon
(A) C2H2 (B) C2H4
(C) CH4 (D) C2H4

4. Highest boiling point is expected for

(A) Iso-octane (B) n-octane
(C) 2,2,3,3-tetramethylbutane (D) n-butane

5. Which hydrocarbon will react with NaNH2 to form sodium salt

(A) Benzene (B) Ethane
(C) Ethene (D) Acetylene
light
6. C3H8 +Cl2   C3H7Cl + HCl is an example of
(A) Substitution (B) Elimination
(C) Addition (D) Rearrangement reaction
7. The main product of dehydrohalogenation of 2-iodobutane
(A) 1-butene (B) 2-butene
(C) n-butane (D) a and b equally

8. A metallic carbide on treatment with water gives a colourless gas, which burns readily
in air and which gives a precipitate with ammonical silver nitrate solution. The
gas evolved is:
(A) methane (B) ethane
(C) ethene (D) acetylene

9. Incorrect equation(s)
(A) CH3CH = CH2 + HCl   CH3CHClCH3
(B) CH3CH = CH2 + HBr   CH3CH2CH2Br
Peroxide
(C) CH3CH = CH2 + HBr   CH3CH2CH2Br
Peroxide
(D) CH3CH = CH2 + HI   CH3CHICH3

10. Halogenation of an alkane is not possible in the presence of

(A) (C6H5CO)2O (B) heat
(C) sunlight (D) (C6H5)2NH

11. Anti Markownikoff addition takes place in following

(C 2 H 5CO)2 O
(A) CH3CH = CH2 + HBr  
Peroxide
(B) CH2 = CH –CH2Cl + HCl  
Peroxide
(C) CH2 = CH - CH2OH + HCl  
Peroxide
(D) CH2 = CH - CH2CH2CH2CH2OH + HCl  

12. The number of structural and configurational isomers of a bromo compound, C5H9Br,
formed by the addition of HBr to 2-pentyne respectively are
(A) 1 and 2 (B) 2 and 4
(C) 4 and 2 (D) 2 and 1

13. The number of sigma and pi bonds in but-1-en-3-yne are

(A) 5 sigma and 5 pi (B) 7 sigma and 3 pi
(C) 8 sigma and 2 pi (D) 6 sigma and 4 pi

14. An organic compound (X) decolorizes bromine water without evolution of HBr.
(X) can be
(A) An alkene (B) An alkane
(C) Cycloalkane (D) Benzene

15. Which of the following statements is/are not correct for alkanes
(A) All C – H and C – C bonds have a length of 1.112Å and 1.54Å respectively.
(B) All bond angles are tetrahedral, having a value of 109.5Å
(C) The C – C chain is linear and not zigzag.
(D) All the above.

16. In the hydrohalogenation of ethene, which intermediate formation takes place;

+ +
(A). H2C CH (B). H3C CH2

-
CH2 -
(C). (D). H2C CH
Cl

17. Choose the reagent for the following process

 H H

C C

C C

(A) sodamide (B) liquid ammonia

(C) LiAlH4 (D) Lindlars catalyst

18. Propyne is prepared by dissolving Mg2 C3 in water. The pH of the resulting solution of the
reaction mixture is
(A) less than 7 (B) greater than 7
(C) equal to 7 (D) can’t be predicted

19. Which one cannot be prepared by Kolbe’s electrolytic process?

(A) C2H2 (B) CH4
(C) C2H4 (D) C2H6

20. Which of the following does not yield alkane:

(A). HC CH + CH3MgCl
(B). H O + CH3MgCl
2

(C). H2C CH2 + CH3MgCl

(D). NH3 + CH3MgCl

21. Identify A:

H3C H
Peroxide
+ DCl [A];

H3C H

CH3 H3C CH3

H3C
(A). (B).
D Cl
Cl D
Cl H3C
Cl
(C). D (D).
H3C H3C
D

22
HgSO4 Zn - Hg Cl2
C CH [A] [B] [C]
dil. H2SO4 HCl AlCl3

Compound [C] can be:

Cl Cl
(A)
(B)
CH CH3 CH2CH3

(C)
CH2CH3 (D) CH2CH2Cl

Cl
23. Cl
1 eq.Mg/ether CH3C CD
[A] ; identify [A]:
Br

Cl D
(A)
(B)
D Br

D
(D) none
(C)

D
24.
H2O/H+
CH CH2 1 equivalent
CH3CO 3H [A]

Compounds [A] can be

HO
OH
(A)
CH CH2 (B) CH CH2
OH HO
HO
HO
(C) (D) OH
CH CH2
CH CH2
HO HO OH

25.
NaNH2 CH3Br H2O H+
H3CO C C H [X] ; What is [X]

O O
(A) CH2CH3
H3CO C (B) H3CO CH2 C CH3

O
(D) H3CO C CH2CH2CH3
(C) H3CO CH2CH2CH2CHO

26. Br
HCl
[X]; Compound [X] is:
peroxide
CH3

(A) Cl – CH = CH – CH3 (B) Br – CH = CH – CH3

Cl
|
(C) Br – CH – CH2 – CH3 (D) Br – CH2 – CH – CH3
|
Cl
27. Br
alc. KOH
H [A] ; compound [A] can be:
CH3

(A) CH3 (B) CH3

(C) CH2
(D) none
28. H
CH3 Br2 (i) alc. KOH
[X] [Y]
H2O (ii) H2O/H+
H3C
CH3
Compound [Y] in the above sequence of reaction:
H3C
CH3
(A) (B) H2C CH3
HO CH3
O
CH2
(C) (D)
H2C H2C
CH3 CH2
CH3

29. HCl
CH3CH CH CH2 CH3 [A]
peroxide

HCl
[B]
Which of the following true for [A] and [B]:
(A) [A] and [B] are same (B) [A] and [B] are functional group isomer
(C) [A] and [B] are positional isomers (D) none

30. How many mono bromo derivative will be formed by neohexane:

(A) 4 (B) 5
(C) 6 (D) none
 ANSWERS
Part – A

1. D 2. B 3. B 4. A
5. C 6. B 7. B 8. C
9. A 10. B 11. B 12. B
13. B 14. B 15. C 16. B
17. D 18 A 19. A 20. B
21. A 22. A 23. C 24. C
25. D 26. D 27. B 28. A
29. B 30. C 31. C 32. D
33. A 34. B 35. A 36. D
36. D 37. C 38. D
Part – B

1. D 2. D 3. B 4. A
5. D 6. D 7. B 8. B
9. B 10. C 11. A 12. B
13. A 14. A 15. C 16. A
17. B 18. A 19. B 20. C
21. A 22. B 23. B 24. A
25. B 26. A 27. B 28. C
29. A 30. A
Part – C

1. D 2. B 3. A 4. B
5. D 6. A 7. B 8. D
9. B 10. D 11. A 12. B
13. B 14. A 15. D 16. B
17. D 18. B 19. B 20. C
21. A 22. B 23. A 24. B
25. A 26. C 27. A 28. B
29. A 30. D