Page # 96 HYDROCARBON

Answers
Exercise-I

1. B 2. A 3. B 4. C 5. B 6.B 7. A

8.A 9. C 10. C 11. D 12. D 13. C 14. C

15. B 16. D 17. C 18. D 19. A 20. B 21. B

22. C 23. A 24. D 25. A 26. A 27. A 28. A

29. B 30. C 31. C 32. A 33. B 34. C 35. B

36. C D 37. ABCD 38. C D 39. ACD 40. ABD 41. T 42. F

Exercise-II

1. D 2. D 3. A 4. D 5. B 6. B 7. B

8. A 9. D 10. A 11. C 12. C 13. C 14. D

15. D 16. D 17. B 18. D 19. C 20. D 21. C

22. C 23. A 24. D 25. D 26. D 27. B 28. B

29. D 30. A 31. C 32. A 33. C 34. D 35. A

36. B 37. B 38. A 39. C 40. B 41. C 42. B

43. B 44. D 45. A 46. A 47. A 48. A 49. C

50. B 51. C 52. C 53. B 54. ACD 55. AC 56. AC

57. AB 58. AC 59. B 60. 44 + 2 = 46

Br

CH – CH2Br
61. (A) 3NaNH2(liq.) CH3I
(B)

62. (a) 2 (b) 2 (c) 2

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 HYDROCARBON Page # 97

Exercise-III
1. D 2. A 3. D 4. A 5. A 6. B 7. C
8. D 9. C 10. A 11. C 12. A 13. C 14. B

15. B 16. A

Exercise-IV

1. B 2. D 3. D 4. C 5. A 6. A 7. B

8. B 9. D 10. C 11. C 12. AD 13. D 14. C

15. D 16. A 17. D 18. AC 19. B 20. A 21. D

22. A 23. D 24. C 25. C 26. B 27. B 28. B

29. B 30. D 31. B 32. A 33. B 34. B 35.A

36. B 37. D 38. A

O
39. (x) = , (Y) = CH 3 – C – (CH2) 4 – CH = O
CH3

40. A 41. B 42. C 43. A 44. B 45. D 46. D

47. B

Exercise-V

1. With Tolen's reagnet (ammoncial AgNO3), C2H2 gives white ppt but CH4 does not
HC CH + AgNO3 + NH4NO3 AgC CAg+ NH4NO3 + H2O
silver acetylide
(white ppt.)

2. Ethyne 3. CH2 = CH2 + Br2 H2C – CH2 Alc. KOH

–2HBr
ethene ethyne
Br Br
H3C H3C CH3
C = O + O = C – CH3 C=C
ozonolysis
4. H3C H3C H
H
propanone ethanal hydrocarbon(A)

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 Page # 98 HYDROCARBON

H3C CH3 Br CH3

C=C + Br2 H3C – C – C – H
H3C H
CH3 Br
'A' (C5H10Br2)

H3C CH3 CH3 CH3

C=C Alk. KMnO4
H3C – C – C – CH3
H3C H
OH OH

Aq. KMnO4
5. CH3 – CH = CH2 + H2O + [O] CH 3 – CH – CH2
propene
OH OH
(propane-1,2-diol)

6. 2-butyne
7. (i) Methane does not react with chlorine in the dark because chlorine atoms are required for this
reaction and chlorine atoms are obtained only in the presence of light.
(ii) It is accordance with Markownikoff's rule which predicts the stability of secondary carbonium ion
over primary carbonium ion.
8. (i) If reaction is carried out in presence of organic peroxide (anti-Markownikoff's rule)
Br
CH3
Organic
CH2 = C – CH3 + HBr H 2C – CH
peroxide
CH3
CH3
2-methyl propene isobutyl bromide
(ii) If they have terminal hydrogen atom,
i.e., R – C C – H
9. sp 3

H3C H3C H3C

KOH (alc)
10. CH – CH – CH2 – CH3 C = CH – CH2 – CH3 + CH – CH = CH2 – CH3
H3C Cl H3C H3C
A
3-chloro-2-methyl pentane 2-methyl pentene-2 4-methyl pentene-2

11. Cyclohexene decolourise the pink colour of Baeyer's reagent while cyclohexane does not give this test.

OH
1% alk. KMnO4
+ [H2O + O]

OH
cyclohexene

12. CH2 KMnO4 CH2OH

+ [H2O + O]
CH2 CH2OH
CH2 CH 2OH
2KMnO4 + 3 + 4H2O  3 + MnO2 + 2KOH
CH2 CH 2OH
13. Ethylene 14. H2SO4, HgSO4

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 HYDROCARBON Page # 99

* Pt
15. CH3 – CH2 – CH – CH = CH2 CH3CH 2 – CH – CH2CH 3
H2
CH3 CH3
(C6H12) (C6H 14)
Optically active Optically active
16. (i) A(C4H8) adds on HBr in the presence and in the absence of peroxide to give same product, C4H9Br,
hence C4H8 must be symmetrical alkene.
 A CH3 – CH = CH – CH3
OH
H2SO4
(CH3)2C = CH 2 CH3 – C = CH2 + H 2O CH 3 – C – CH 3
(ii) B  isobutene (2-methyl propene)
CH3 CH 3
optically inactive

R R
17. C=C
H H

18. (i) Gas A

CH3 – CH = CH – CH3 2CH3CHO
(ii) Zn/H2O
butene-2
Hence, gas A is ozone because in above reaction, ozonolysis of butene-2 takes place.
Low
Gas A + KOH (dry) B + C
temp.
(deep red coloured) (gas)
Thus, compound A= Ozone (O3)
Compound C = Oxygen (O2)

Me Me
H Br Br H
19. +
Br H H Br

Me Me

H2
20. (C5H8) C5H 12
compound E (hydrogenation) compound F

Ozonolysis
HCHO + H 3C – C – CHO
formaldehyde
O
2-ketopropanal

Hence, compound E must be diene.

CH2 = C – CH = CH2
CH3
Compound F = CH3 – CH – CH2 – CH3

CH3

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Page # 100 HYDROCARBON

Br OH

21. (a) (CH3 – CH2)CH – CH – CH 3 (b) (CH3 – CH2)2C – CH – CH3 (c) (C2H5)3C – OH

Br
22. 3, 4-dibromo-1-butene (at low temperature)
H2/Pt
23. Compound A one mole
n-hexane.
Hence, in compound A six C-atoms are present in straight chain and it is alkene. Compound A on
vigorous oxidation gives single carboxylic acid i.e., it is symmetric alkene i.e., alkene is hexene-3.
CH3 – CH2 – CH = CH – CH2 – CH3
H2
CH 3 – CH 2 – CH 2 – CH2 – CH 2 – CH 3
Pt
n-hexane
Hence, A is hexene-3 [CH3 – CH2 – CH = CH – CH2 – CH3]

24. (A) (B)

25. (A) CH3 – CH2 – CH = CH – CH2 – CH3 (B) CH3CH2COOK

26. Resonance is present in 1, 3-butadiene that's why every bond acquire the character of partial double
bond.
27. In allene CH2 = C = CH2

sp2 sp sp2 – hybrid state

The -bonds between C1 and C2 are perpendicular to that of C2 and C3 by p – p overlapping.
Therefore, the hydrogen attached to C1 and those attached to C2 are in different planes (i.e., perpendicular).
-bonds between C1 – C2 and C2 – C3 are sp2 – sp and sp – sp2 overlapping on their axes.
28. 1 ozonolysis; 2 LiAlH4 or H2/Ni ; 3 conc. H2SO4
29. (1) NaNH2, (2) Me – I (3) HgSO4 dil H2SO4
30. higher electronegativity of sp carbon
31. In presence of Lindlar's catalyst (Pd and CaCO3 in quinoline) partial hydrogenation takes place and cis
isomer is obtained.

H2 CH3
CH3 Lindlar catalyst

32. (X)
CH3

O
(Y) CH3 – C – (CH2)4 – CH = O

33. 5

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