HYDROCARBION - JEE Page 84

6. HYDROCARBON
EXERCISE - I
1. Petroleum mainly contains 8. Isobutylene react with HOCl gives
(1) Mixture of alkanes
(2) Mixture of esters OH

(3) Mixture of aromatic compounds (1) CH3 C CH2Cl

(4) Mixture of olefines CH3
Ni
2. The reaction CH 2 CH 2 +H 2 
250  300 C

CH3
CH 3 —CH 3 is called
(1) Wurtz reaction (2) CH3 C CH2OH

(2) Kolbe's reaction Cl

(3) Sabatier - Senderens reaction

(3) CH3 CH CH2OH
(4) Cabylamine reaction
CH2 Cl
3. A compound responds to Baeyer's test but does not
give white precipitation when treated with ammonical
silver nitrate solution the compound should be (4) CH3 C O + CH3Cl
(1) C2H6 (2) C3H4 CH3
(3) C2H2 (4) C2H4
9. On heating sodium propionate with sodalime the
4. Pyrolysis of ethyl acetate gives hydrocarbon obtained is
(1) CH3COCH3 (2) CH2 CH2 (1) Butane (2) Ethane
(3) CH2 C O (4) CH3—CHO (3) Propane (4) Ethene
10. If the products of ozonolysis are acetone and
5. When CH3—CH CHBr reacts with HBr in presence
of peroxide the product will be formaldehyde, what is the initial compound?
(1) CH3—CH2—CHBr2 (1) CH3 C C CH3 (2) CH3 C C H
Br Br CH3 CH3 CH3 CH3
(2) CH3 CH CH2
(3) CH3 C C H (4) CH3 C CHC2H5
(3) CH2 CH2 CH2
CH3 H CH3
Br Br
11. What is the product of the reaction -
(4) CH3—CBr2—CH3
peroxide
CH 2 CH(CH 2) 6 —CH 3 
HBr
?
6. In the formation of alkene when alcoholic KOH reacts
with CH3CH2Cl what is the attacking species in the
reaction. (1) CH3 CH (CH2)6 CH3
(1) C2H5O (2) OH Br
 
(3) H 3 O (4) K (2) CH2 CH2 (CH2)6CH3
Br
7. What is the weight of bromine needed for the reaction
with 21 gm of C3H6
(3) CH3 CH2 CH(CH2)6CH3
(atomic weight of Br 80)
(1) 40 g (2) 80 g Br
(3) 160 g (4) 120 g (4) None of above

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12. Review the following reactions and choose those 18. Tollen's reagent is
reactions which are completed by free radical mechanism (1) Ammonical cuprous chloride
(2) Ammonical cuprous oxide
Br
(3) Ammonical silver bromide
HBr
(a) CH3 C CH2   CH3 C CH3 (4) Ammonical silver nitrate
CH3 CH3 19. Compounds capable of reacting with ammonical
HBr
(b) CH 3—CH CH 2 
Peroxide  CH 3 CH 2 CH 2 Br AgNO3 solution are
CH 2 N 2
(c) CH3—CH CH2 
 CH3 CH CH3 (1) CH3 CH C CH (2) HC CH
CH2 CH3
h
(d) CH 4+Cl 2   CH 3Cl +HCl
(1) b, c, d (2) a, b (3) a, c (4) a, d (3) 1- Butyne (4) all the above
13. The correct order of bond strength is 20. In the reaction sequence
(1) C—C < C C < C C
Hg 2
Ni
(2) C C < C C < C—C H2 O
CaC2    A 
dil H2 SO 4
 B 
H2
C
(3) C C < C C < C—C
the product C is
(4) C C < C—C < C C
(1) CH 3—OH (2) CH3CHO
14. Lindlar's catalyst is (3) C2H5OH (4)C 2 H 4
(1) Pt in ethanol (2) Pd + CaCO 3
21. In the reaction
(3) Ni in ethanol (4) Na in liquid NH 3
(i) X
CH 3 —C C—CH 3 
( ii ) H 2 O / Zn

2 CO  H O
15. The reaction : CH3—CH CH 2 
H

CH3 C C CH3 ; X is
CH3 CH CH3 is known as O O
COOH (1) HNO3 (2) O2
(1) Wurtz reaction (2) Koch reaction (3) O3 (4) KMnO4
(3) Clemensen reduction (4) Kolbe's reaction 22. HC CH + 2HOCl  compound A
16. In the reaction is
(1) Glyoxal (2) Chlorohydrin
KMnO 4
CH 3 CH CH 2 + H 2O + [O] 
Acid
 (3) Dichloro acetaldehyde (4) Formic acid

[O ] 23. Lewisite a war gas is obtained by the action of acety-

CH3 CH CH2  X + HCOOH X is:-
lene on
OH OH (1) COCl2 (2) SOCl2 (3) AsCl3 (4) AlCl3
24. Olefin, which gives CH3CHO and CH3CH 2CHO
(1) CH3CH2COOH (2) CH3COOH
on ozonization and hydrolysis is:
(3) CH3CH2CHO (4) CH3CH2OH (1) 1–butene (2) 2–butene
17. Addition of two molecules of HBr to CH3—C CH (3) 1–pentene (4) 2–pentene
2
gives 25. CH
Hg
CH 
CH 3 MgX / H 2 O
 B  [O ]
 C  D
H SO 2 4

(1) CH 3—CBr 2 —CH 3 (2) CH3 CH CH2 End product D will be

Br Br (1) Acetaldehyde
(2) Isopropyl alcohol
(3) CH 3 —CH 2—CHBr 2 (4) CH3 CH2 CH2 (3) Ethyl alcohol
Br Br (4) Acetone

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HYDROCARBION - JEE Page 86
26. Which of the following molecule shows dipole moment 32. What is the product formed when 1-butene is heated
with Al 2(SO 4)3 at 500K
(1) 2, 2–dimethyl propane (1) CH 3CH 2CH 2CH 3
(2) Trans -2 - pentene (2) CH 2 CH—CH CH 2
(3) Trans 3– Hexene
(3) (CH3) 2C CH 2
(4) 2, 2, 3, 3– Tetra methyl butane
(4) (C4H8) n
27. According to Markownikoff rule product formed by 33. n-hexane when under pressure passed over heated
reaction on 1–butene with water catalyst (Chromic oxide supported over alumina)
at 750K gives
(1) Primary alcohol (2) Secondary alcohol
(1) Cyclohexene (2) 1,3 hexadiene
(3) Tertiary alcohol (4) None of these
(3) 1,5 hexadiene (4) benzene
28. Acetone formed by following ozonolysis
34. Acetylene on reaction with Alkaline KMnO 4 forms
(1) 1-butene (2) 2-butene
(1) CH 2 CH 2 (2) Oxalic acid
(3) Iso butene (4) Butyne
(3) CH3COOH (4) CO 2 + H 2 O
29. Which of the following give H 2 gas with Na
35. The compound on ozonolysis and followed by
(1) CH4 (2) C2H 6
reduction gives two mole of acetaldehyde. The ‘X’
(3) C2H 4 (4) C2H 2
is
30. What is the main product of the reaction between (1) 2–butene (2) 1,3–butadiene
2-methyl propene with HBr (3) 1–butene (4) Isobutene
(1) 1-bromo butane
36. Which one of the following is reduced with Zn–Hg
(2) 1-bromo-2-methyl propane
and hydrochloric acid to give the corresponding
(3) 2-bromo butane
hydrocarbon ?
(4) 2-bromo-2-methyl propane
(1) Acetamide (2) Acetic acid
31. What product of the following reaction is (3) Ethyl acetate (4) Butan-2-one
CH3 CH C CH3 +HCl  37. Addition of HI on double bond of propene yields
CH3 isopropyl iodide and not n-propyl iodide, because
addition proceeds through
CH3 (1) A more stable carbanion
(1) CH3 CH2 C CH3 (2) A more stable carbonium ion
Cl (3) A more stable free radical
(4) None
CH3
38. Propane can be distinguished from propylene with
(2) CH3 CH C CH3
(1) Sodium (2) Bromine water
Cl H (3) ammonical AgNO 3 (4) NaHSO 3
CH3 39. Compound 'A' on chlorination gives compound 'B'
compound 'B' reacts with alc. KOH gives gas 'C',
(3) CH3 CH2 CH CH2 Cl
which decolourise Baeyer reagent. ozonolysis of
CH3 compound 'C' gives only HCHO compound. 'A' is:
(4) Cl CH2 CH2 CH CH3 (1) C 2H 6 (2) C 2H 4
(3) C 4H 10 (4) C 2H 5Cl

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40. Which reagent converts propene to 1–propanol 47. The treatment of benzene with isobutene in the presence
(1) H2O, H2SO4 of sulphuric acid gives
(2) B 2H6, H2O2, OH– (1) Isobutyl benzene. (2) t–butyl benzene.
(3) Hg(OAc)2,NaBH4/H 2O
(3) n–Butyl benzene (4) No reaction.
(4) Aq. KOH
41. Correct order of stability is 48. The major product obtained on treatment of
–
(1) 1–butene > Trans– 2–butene > Cis– 2–butene CH3CH2CH(F)CH3 with CH3O /CH3OH is
(2) Trans– 2–butene > 1–butene > Cis– 2–butene (1) CH 3CH 2CH(OCH 3)CH 3
(3) Trans– 2–butene > Cis– 2–butene > 1–butene
(2) CH3CH CHCH 3
(4) Cis–2 butene > Trans– 2–butene > 1–butene
(3) CH 3CH 2CH CH 2
42. CH3 CH2 CH CH3 obtained by chlorination of (4) CH 3CH 2CH 2 CH 2OCH 3
Cl
49. 3–Phenyl propene on reaction with HBr gives (as
n–butane, will be
a major product)
(1) Meso form (2) Racemic mixture
(3) d–form (4) –form (1) C 6H 5CH 2CH(Br)CH 3
43. Which alkene on ozonolysis gives CH3CH2CHO (2) C 6H 5CH(Br)CH 2CH 3
(3) C 6H 5CH 2CH 2CH 2Br
and CH3CCH3
(4) C6H5CH(Br)CH CH 2
O
CH3
(1) CH3CH2CH
C 50. Products of the following reaction
CH3
3(1) O
(2) CH3CH2CH CHCH2CH3 CH3C C.CH2CH3   
(2) H ydrolysis are
(3) CH3 CH2 CH CHCH3
(1) CH3COOH + CH3COCH 3
(4) CH3 C CHCH3
(2) CH3COOH + HOOC.CH2CH 3
CH3
(3) CH3CHO + CH3CH 2CHO
44. An organic compound A(C4H9Cl) on reaction with (4) CH3COOH + CO2
Na/diethyl ether gives a hydrocarbon which on
51. Reduction of aldehydes and ketones into
monochlorination gives only one chloro derivative
hydrocarbons using zinc amalgam and conc. HCl
then, A is
(1) t–butyl chloride (2) Sec. butyl chloride is called
(3) Iso butyl chloride (4) n–butyl chloride (1) Cope reduction
(2) Dow reduction
45. When CH3CH 2CHCl2 is treated with NaNH2, the
(3) Wolf-kishner reduction
product formed is :
(1) CH 3 —CH CH 2 (2) CH 3—C CH (4) Clemmensen reduction

NH2 Cl 52. C.N.G. is -

(3) CH3CH2CH (4) CH3CH2CH
NH2 NH2 (1) CH4 + Propane + Butane + Higher Alkane

46. The compound CH3 C (84%)

CH CH3 on reaction
(2) CH4 + Ethane + Butane
CH3
(33%) (33%) (33%)
with NaIO4 in the presence of KMnO4 gives:
(3) Benzene + petrol
(1) CH3COCH3
(1 1)
(2) CH3COCH 3 + CH3COOH
(3) CH3COCH 3 + CH 3CHO (4) CH4 + LPG
(4) CH 3CHO + CO 2 (10%) (90%)
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HYDROCARBION - JEE Page 88

53. 2-Bromopentane is heated with potassium ethoxide in 54. Which of the following acidity order is correct -
ethanol. The major product obtained is - (1) 1-Alkyne > Alkene > Alkane
(1) 1-Pentene (2) cis-2-pentene (2) Alkene > Alkane > 1-Alkyne
(3) trans-2-pentene (4) 2-Ethoxypentane (3) Alkane > Alkene > 1-Alkyne
(4) None of these

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EXERCISE - II
1. The smalle st alkane which can show optical 8. Consider the following reaction-
1.BH
isomerism possesses - CH3CH=CH 3
2 2.C H 3 COOH

(1) 5 carbons (2) 6 carbons The product formed is

(3) 7 carbons (4) 8 carbons (1) CH3CH2CH2OH (2) CH3CH(OH)CH3

2. The appropriate reagent for the transformation (3) CH3CH2CH3 (4) CH2–CH2
O CH2
9. The major component of LPG is -
CH3
is- (1) methane (2) ethane
HO HO (3) propane (4) isobutane
(1) Zn(Hg)/HCl (2) NH2NH2,OH–
10. The following conversion
(3) H2/Ni (4) NaBH4
R R H
3. Ethylmagnesium bromide reacts with methanol to
C=O C
produce - R R H
(1) methane (2) methoxyethane cannot be effected by
(3) ethane (4) propane (1) Clemmensen reduction
(2) Wolff-Kishner reduction
4. An aqueous mixture of sodium ethanoate and (3) Wurtz reaction
sodium propanoate is electrolyzed. The product (4) Red P and HI at 200ºC
of the reaction is-
11. Which of the following halogen reacts with alkanes
(1) CH3 CH 2 CH 3 (2) CH 3 CH 2 CH 2 CH 3
with explosive violence -
(3) CH3 CH 3 (4) all of these
(1) F2 (2) Cl2

5. Monochlorination of ethylbenzene (PhCH2CH3) with (3) Br2 (4) I2

Cl2 under heat produces -

12. The major product formed in the dehydration of 1–
(1) PhCH2CH2Cl (2) PhCHClCH3
butanol by heating with concentrated H2SO4 is -
(3) both (1) and (2) in equal amounts
(1) trans–2–butene
(4) more of (2) and less of (1)
(2) cis–2–butene
6. The least reactive alkane towards free-radical (3) 1–butene
substitution reactions is- (4) 1, 3–butadiene
(1) CH4 (2) (CH3) 3CH
(3) CH3CH3 (4) CH3CH2CH3 13. For the reaction
7. Raney nickel, which is used as a catalyst, is obtained H2SO4
by- CH2OH

(1) grinding solid nickel the major product is

(2) by treating nickel–aluminium alloy with dilute
NaOH (1) CH2 (2) CH3

(3) by treating nickel–aluminium alloy with dilute

HCl (3) (4)
(4) by heating nickel tetracarbonyl

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HYDROCARBION - JEE Page 90

14. Propene is allowed to react with B2D6 and the product 20. Propene on reaction with N–bromosuccinimide in
is treated with acetic acid. The final product obtained
CCl4 produces -
is -
(1) 1, 2–dibromopropane
(1) 1–deuteriopropane (2) 2–deuteriopropane
(3) 1–deuteriopropene (4) 2–deuteriopropene (2) 3–bromopropene
(3) 1–bromopropene
15. Ethylene reacts with Br 2 to give
(4) 2–bromopropene
1,2 dibromoethane. The anti-addition takes place
due to the formation of the intermediate- 21. 1–Methylcyclohexene is allowed to react with B2H6.
+ The product is then treated with H2O2 and NaOH.
(1) CH2Br–CH2 (2) CH2– CH2
+ The reaction is -
Br
1.B2H6
–
(3) BrCH=CH + (4) CH2– CHBr 2.H2O2/OH
+ CH3
Br
The product formed is
16. Propene on reaction with Br2 in CCl4 yields-
(1) 1–methylcyclohexanol
(1) 1,2–dibromopropane
(2) 2–methylcyclohexanol
(2) trans–1,2–dibromopropane
(3) (±) trans–2–methylcyclohexanol
(3) (±) 1,2–dibromopropane
(4) (±) cis–2–methylcyclohexanol
(4) 3–bromopropane
22. Which of the following alkyl halides undergoes the
17. Propene on reaction with Cl2 at 600º produces - fastest base–induced dehydrohalogenation
(1) 1, 2–dichloropropane (1) t–Butyl iodide (2) t–Butyl bromide

(2) 1–chloropropane (3) Isobutyl bromide (4) s–Butyl iodide

(3) 3–chloropropene
23. In the presence of a peroxide, which of the following
(4) 2–chloropropene hydrogen halides undergoes addition reaction with
18. cis–2–Butene on reaction with Br2 in CCl4 produces propene in an anti-Markovnikov fashion
mainly - (1) HF (2) HCl
(1) 1–bromo–2–butene (3) HBr (4) HI
(2) 2,3–dibromobutane
24. Propene on reaction with ICl produces mainly -
(3) meso–2,3–dibromobutane
(1) 1–chloro–2–iodopropene
(4) (±) 2,3–dibromobutane
(2) 2–chloro–1–iodopropane
19. Which of the following reactions will result in the (3) (±)–2–chloro–1–iodopropane
formation of a chiral centre in the product - (4) (±)–1–chloro–2–iodopropane
(1) CH 3 CH=CH 2 +HBr 
25. cis–2–Butene on reaction with cold dilute KMnO4
(2) CH 2 =CH2 +HOBr 
solution produces -
H2O2
(3) CH3CH2CH=CH2+HBr  (1) meso–2,3–butanediol (2) (±) 2,3–butanediol
(4) CH3CH2CH=CH2+HBr  (3) 2, 3–butanedione (4) 1,2–butanediol
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32. In the reaction

26. Consider the following reaction
1.Hg ( OAc ) ,H O
CH3CH2CH=CH
2
2
2.NaBD 4
2

diluteKM nO 4
CH2=CH2 HOCH2–CH2OH
H 2 O ,NaOH the product obtained is -

Which of the following statements is correct about (1) CH3CH2CHOHCH2D

the procurement of two oxygens in the product ? (2) CH3CH2CHDCH2OH

(3) CH3CH2CD(OH)CH3
(1) Both are procured from KMnO4
(4) CH3CH2CD2CH2OH
(2) Both are procured from H2 O
(3) Both are procured from NaOH 33. The major product obtained in the reaction of 1,3-
Butadiene with HCl (1 mole) at a higher temperature
(4) One is procured from KMnO4 and the other
(100ºC or above) is
from NaOH
(1) 3,4–dichloro–1–butene
27. Which of the following will give the best yield of 2– (2) 3–chloro–1–butene
pentene on reaction with C2H5ONa/C2H5OH (3) 1–chloro–2–butene

(1) 2–Iodopentane (2) 2–Bromopentane (4) 2–chloro–2–butene

(3) 3–Iodopentane (4) All equally satisfactorily

34. The major product formed by the addition of
1 mole of HCl to 1,3-Butadiene at a low
28. Consider the reaction
temperature (0ºC or below) is
CH3
+ – Heat (1) 3–chloro–1–butene
CH3CH2CH2–N–CH2CH3 OH
CH3 (2) 1–chloro–2-butene
Which of the following is formed in major amount (3) 2–chloro–2–butene
(1) CH2=CH2 (4) Chlorocyclobutane
(2) CH3CH2=CH2
(3) Both (1) and (2) in equal amount 35. An optically active hydrocarbon (X) on catalytic
(4) None, as no reaction takes place hydrogenation gives an optically inactive
compound (Y), C6 H14 . The hydrocarbon (X) is-
29. The synthetic fibre orlon is prepared by the
polymerization of - (1) 3–methyl–1–pentene

(1) chloroethene (2) propene (2) 3–methyl–2–pentene

(3) propenenitrile (4) 2–chloro–1,3–butadiene (3) 2–ethyl–1–butene (4) 3–methylcyclopentene
30. A hydrocarbon C6H10 absorbs only one molecule of
H2 on catalytic hydrogenation. On ozonolysis, the 36. trans–2–Butene is allowed to react with D2 in the
hydrocarbon yields CHO(CH2)4CHO. The hydrocarbon presence of nickel as catalyst. The product formed is-
is - (1) (±)–2,3–dideuteriobutane
(1) cyclohexene
(2) meso–2,3–dideuteriobutane
(2) 1,5–hexadiene
(3) 1,4–dideuterio–trans–2–butene
(3) 1,3–cyclohexadiene
(4) 2,3–dideuteriobutane
(4) 1–methylcyclopentene

31. In the addition of HBr to propene in the absence of a 37. The addition of HCl to 1–phenylpropene gives-
peroxide, the first step involves the addition of -
(1) C6H5CHClCH2CH3 (2) C6H5CH2CHClCH3
(1) H+ (2) Br–
(3) C6H5CH2CH2CH2Cl (4) C6H5CH(CH3)CH2Cl
(3) H  (4) Br 
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HYDROCARBION - JEE Page 92

38. The reduction of 4–octyne with H2 in the presence 45. The reaction of RCH=CH2 with B2H6 followed by
of Pd/CaCO3 – quinoline gives- oxidation with alkaline H2O2 gives -
(1) trans–4–octene
(1) RCH(OH)CH2OH (2) R–COCH3
(2) cis–4–octene
(3) RCH2CH2OH (4) RCH2CHO
(3) a mixture of cis–and trans–4–octene
46. The major product obtained by the treatment of
(4) a completely reduced product C8H18
propyne with aqueous H2SO4 in the presence of
39. Which of the following alkanes gives only one HgSO4 is -
monochlorinated product-
(1) propanal
(1) CH3 CH 2 CH 3 (2) CH 3 CH 2 CH 2 CH 3 (2) acetone
(3) (CH3)4C (4) CH3(CH2)3CH3 (3) propanol
40. The ease of formation of free radicals follows the (4) propyl hydrogen sulphate
order - 47. The major product of the debromination of meso–
 
dibromobutane is-
(1) 3 º  2 º  1 º  C H 3 (2) C H 3  1 º  2 º  3 º
(1) n–butane (2) 1–butene
 
(3) 1 º  2 º  3 º  C H 3 (4) 2 º  1 º  3 º  C H 3 (3) trans–2–butene (4) cis–2–butene

41. Which of the following has the lowest heat of 48. Which of the following will not react with an
hydrogenation per mole - ammonical silver nitrate solution-
(1) CH3 C CH (2) (CH3 )2CH–CH
(1) cis–2–Butene (2) trans–2–Butene
(3) CH3CCCH3 (4) HCCH
(3) 1–Butene (4) 1,3–Butadiene
49. The product obtained in the reaction
42. The reaction of 1–butene with HBr in the presence
CH3 H Br2
of peroxide gives - is
C=C
(1) 2–bromobutane (2) 1–bromobutane H CH3
CH3 CH3
(3) 1,1–dibromobutane (4) 1, 2–dibromobutane
H Br H Br
43. The intermediate formed during the addition of HCl (1) (2)
H Br Br H
to propene in the presence of peroxide is- CH3
CH3
 
(1) CH 3 C HCH 2 Cl (2) CH 3 CH 2 C H 2
  CH3 CH2Br
(3) CH 3 C HCH 3 (4) CH 3 C H 2 C H 2 Br H H
H
(3) (4)
44. The order of stability of the alkenes H Br H H

R2C=CR2, R2C=CHR, R2C=CH2, CH3 CH2Br

I II II 50. The bond dissociation energies of the following

RCH=CHR, and RCH=CH2 CH3–H CH3CH2–H CH2=CH–CH2–H C6H5–H

IV V I II III IV
vary in the order
is -
(1) I > II > III > IV (2) IV > III > II > I
(1) I > II > III > IV > V (2) I = II > III > IV > V (3) IV > I > II > III (4) II > I > IV > III
(3) II > I > IV > III > V (4) V > IV > III > I > II
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 Page 93 HYDROCARBION - JEE

EXERCISE - III (PREVIOUS YEAR QUESTION)

1. Alcoholic solution of KOH is a specific reagent for

7. In the compound CH 2 =CH–CH 2 –C  CH, the
[IIT -90]
C2–C3 bon is of the type [IIT -99]
(1) Dehydration (2) Dehydrogenation (1) sp–sp2 (2) sp2–sp3
(3) Dehydro halogenation (4) Dehalogenation (3) sp–sp3 (4) sp3–sp3

2. 1–chlorobutane on reaction with alcoholic potash 8. Which one of the following alkenes will react fastest
gives [IIT -91] with H2 under catalytic hydrogenation condition -
(1) 1–butene (2) 1–butanol [IIT-2000]

(3) 2–butene (4) 2–butanol R R R H

(1) (2)
3. The product (s) obtained via oxymercutation (HgSO4
H H R H
+ H2SO4) of 1–butyne would be - [IIT-92, 99]

(1) CH 3  CH 2  C – CH 3 R R R R
||
O (3) (4)
R H R R
(2) CH3–CH2–CH2–CHO
9. Propyne and propene can be distinguished by -
(3) CH3–CH2–CHO–HCHO
[IIT-2000]
(4) CH3–CH2–COOH+HCOOH
(1) conc. H2SO4 (2) Br2 in CCl2
(3) dil.KMnO4 (4) AgNO3 in ammonia
4. Which is the decreasing order of strength of bases
10. In the presence of peroxide, hydrogen chloride and
OH–, NH 2 , HC  C– and CH3– CH 2 [IIT -93]
hydrogen iodide do not give anti-Markovnikov
(1) CH3– CH 2 > NH 2 > HC  C– > OH–
addition to alkene because - [IIT Screening-2001]
(2) HC  C– > CH3– CH 2 > NH 2 > OH– (1) Both are highly ionic
(3) OH– > NH 2 > HC  C– > CH3– CH 2 (2) One is oxidising and the other is reducing
(4) NH 2 > HC  C– > OH– > CH3– CH 2 (3) One of the step is endothermic in both the cases
(4) All the steps are exothermic in both cases
5. The chief reaction product of reaction between 11. The reaction of propene with HOCl proceeds via
n-butane and bromine at 130º C is - [IIT -95] the addition of - [IIT S c reening -2001]
(1) H+ in the first step
(1) CH3CH2CH2CH2Br (2) CH3CH2CHBr
(2) Cl+ in first step
CH3
(3) OH– in first step
(4) Cl+ and OH– in single step
(3) CH3–CHCH2Br (4) CH3–C–Br2
12. The nodal plane in the -bond of ethene is located
CH3 CH3
in - [IIT S c reening -2001]
(1) the molecular plane
6. When cyclohexane is poured on water, it floats, (2) a plane parallel to the molecular plane
because - [IIT -97] (3) a plane perpendicular to the molecular plane
(1) Cyclohexane is in 'boat' form which contains the carbon-carbon -bond at right
(2) Cyclohexane is in 'chair' form angle
(3) Cyclohexane is in 'crown' form (4) a plane perpendicular to the molecular plane
which contains the carbon-carbon -bond
(4) Cyclohexane is less dense than water
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HYDROCARBION - JEE Page 94

13. Consider the following reactions -

OH  X
[IIT S c reening -2002] 18.
H
 
 2

Br
 5
H O
2 (Mixture )
H3C–CH–CH–CH3+Br  'X' + HBr
compounds of molecular formula C 4H8Br2.No. of
D CH3 compounds X will be [IIT S c reening -2003]
Identify the structure of the major product 'X' (1) 2 (2) 3
(3) 4 (4) 5
(1) H3C–CH–CH–CH2
D CH3 19. 1–Butene may be converted to butane by reaction
with - [ A I E E E- 2 0 0 3 ]
(2) H3C–CH–C–CH3
(1) Pd/H2 (2) Zn - HCl
D CH3
(3) Sn - HCl (4) Zn - Hg/HCl
(3) H3C–C–CH–CH3
20. On mixing a certain alkane with chlorine and
D CH3
irradiating it with ultraviolet light, it forms only one
monochloroalkane. This alkane could be -
(4) H3C–CH–CH–CH3
[ A I E E E- 2 0 0 3 ]
CH2D
(1) neopentane (2) propane
(3) pentane (4) isopentane
14. Identify a reagent from the following list which can
easily distinguish between 1–butyne and 2–butyne 21. 2–hexyne can be converted into trans –2–hexene
(1) Bromine, CCl4 [IIT S c reening -2002] by the reaction of - [IIT S c reening -2004]
(2) H2, Lindlar catalyst (1) H2/Pd/BaSO4 (2) Li in Liquid NH3
(3) dilute H2SO4, HgSO4 (3) H2/PtO2 (4) NaBH4
(4) ammonical Cu2Cl2 solution
22. Which one of the following is reduced with
15. Which of these will not react with acetylene - Zn-Hg/HCl to give the corresponding hydrocarbon
[ A I E E E- 2 0 0 2 ] [AIEEE-2004]
(1) NaOH (2) ammonical AgNO3 (1) Butane-2-one (2) Acetic acid
(3) Na (4) HCl (3) Acetamide (4) Ethyl acetate
23. Amongst the following compounds, the optically
16. What is the product formed when acetylene reacts
active alkane having lowest molecular mass is :
with hypochlorous acid - [ A I E E E- 2 0 0 2 ]
[AIEEE-2004]
(1) CH3COCl (2) ClCH2CHO
CH3
(3) Cl2CHCHO (4) ClCH2COOH |
(1)CH3–CH2–CCH (2) CH3–CH2–CH–CH3

HgSO 4
17. C6H5 – CC – CH3 
H 2 SO 4
A H
|
[IIT S c reening -2003] (3) CH3–C– (4) CH3–CH2–CH2–CH3
|
C2H5
O
(1) (2) 24. Which one of the following has the minimum boiling
O
point : [AIEEE-2004]

(3) C6H–C=CHCH (4) C6H5–CH=C–CH3 (1) isobutane (2) 1–butyne

5 3
(3) 1–butene (4) n–butane
OH OH

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 Page 95 HYDROCARBION - JEE

25. 1–Bromo–3–chloro cyclobutane on reaction with 31. CH3–CH=CH2 

NOCl
 Product, product is :
2–equivalent of sodium in ether gives -
[IIT-2005] (1) CH3–CH–CH2–NO [IIT-2006]

Cl Cl
Br
(1) (2)
(2) CH3–CH–CH2–Cl
NO
(3) (4)
(3) CH3–CH–CH
2 2–Cl

26. 2-Methylbutane on reacting with bromine in the (4) NO–CH2–CH–CH

2 2–Cl
presence of sunlight gives mainly
(1) 2–bromo-2–methylbutane [AIEEE-05]
(2) 1–bromo-2–methylbutane Me
(3) 1–bromo-3–methylbutane 32. OH

Me
(4) 2–bromo-3–methylbutane N
Et
27. Alkyl halides react with dialkyl copper reagent to n Bu

give [AIEEE-05]
(1) alkyl copper halides The alkene formed as a major product in the above
(2) alkenes elimination reaction is- [AIEEE-06]
(3) alkenyl halides
(1) (2) CH 2 =CH 2
(4) alkanes Me

28. Reaction of one molecule of HBr with one molecule Me Me

of 1,3–butadiene at 40°C gives predominantly (3) (4)
(1) 1–bromo–2–butene under thermodynamically
controlled conditions [ AI E EE - 05 ]
(2) 3–bromobutene under kinetically controlled 33. Reaction of trans-2-phenyl-1-bromocyclo pentane
conditions on reaction with alcoholic KOH produces-
(3) 1–bromo–2–butene under kinetically controlled (1) 4-phenyl cyclopentene [AIEEE-06]
conditions (2) 2-phenyl cyclopentene
(4) 3–bromobutene under thermodynamically (3) 1-phenyl cyclopentene
controlled conditions
(4) 3-phenyl cyclopentene
29. Acid catalyzed hydration of alkenes except ethene
leads to the formation of [AIEEE-05] 34. Phenyl magnesium bromide reacts with methanol
(1) secondary or tertiary alcohol to give- [AIEEE-06]
(2) primary alcohol (1) A mixture of anisole and Mg(OH)Br
(3) mixture of secondary and tertiary alcohols (2) A mixture of benzene and Mg(OMe)Br
(4) mixture of primary and secondary alcohols (3) A mixture of toluene and Mg(OH)Br
(4) A mixture of phenol and Mg(Me)Br
30. Elimination of Hydrogen bromide from
2–bromobutane results in the formation of 35. Which of the following reactions will yield, 2, 2-
[ AI E EE - 05 ] dibromopropane [AIEEE-2007]
(1) predominantly 2–butene (1) CH 3 —C CH + 2HBr 
(2) equimolar mixture of 1 and 2–butene (2) CH 3 CH CHBr + HBr 
(3) predominantly 2–butyne (3) CH CH + 2HBr 
(4) predominantly 1–butene (4) CH 3 — CH CH 2 + HBr 

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HYDROCARBION - JEE Page 96

41. The treatment of CH 3 MgX with CH 3C  C–H

36. The reaction of toluene with Cl 2 in presence of
produces [AIEEE-2008]
FeCl 3 gives predominantly-
(1) benzoyl chloride [AIEEE-2007] (1) CH 3–CH=CH 2 (2) CH3C  C–CH3

(2) benzyl chloride H H

(3) o-and p-chlorotoluene | |
(3) CH3—C=C—CH3 (4) CH4
(4) m-chlorotoluene
42. One mole of a symmetrical alkene on ozonolysis
37. Presence of a nitro group in a benzene ring gives two moles of an aldehyde having a molecular
mass of 44 u. The alkene is :- [ A I E E E - 2 0 1 0 ]
[AIEEE-2007]
(1) ethene (2) propene
(1) activates the ring towards electrophilic
(3) 1-butene (4) 2-butene
substitution
43. The synthesis of 3–octyne is achieved by adding
(2) renders the ring basic a bromoalkane into a mixture of sodium amide
and an alkyne. T he bromoalkane and alkyne
(3) deac tivates the ring towards nucleophilic
respectively are – [ I IT - 2 01 0 ]
substitution
(1) BrCH 2CH 2CH 2CH 2CH 3 and CH 3CH 2C CH
(4) deactivates the ring towards electrophilic (2) BrCH 2CH 2CH 3 and CH 3CH 2CH 2C CH
substitution (3) BrCH 2CH 2CH 2CH 2CH 3 and CH 3C CH
(4) BrCH 2CH 2CH 2CH 3 and CH 3CH 2C CH
38. The compound formed as a result of oxidation of
44. Ozonolysis of an organic compound gives
ethyl benzene by KMnO 4 is- formaldehyde as one of the products. This confirms
the presence of :- [AIEEE-2011]
(1) benzophenone [AIEEE-2007]
(1) an isopropyl group
(2) acetophenone
(2) an acetylenic triple bond
(3) benzoic acid
(3) two ethylenic double bonds
(4) benzyl alcohol (4) a vinyl group
39. In the following sequence of reactions, the alkene 45. 2–Hexyne gives trans –2–Hexene on treatment
affords the compound ‘B’ :- [AIEEE-2008] with :- [AIEEE-2012]

H 2O
(1) Li AlH4 (2) Pt/H2
CH3CH=CHCH3 
O3
 A 
Zn
 B.
(3) Li/NH3 (4) Pd/BaSO 4
The compound B is 46. In the given transformation, which of the following
is the most appropriate reagent ? [AIEEE-2 01 2 ]
(1) CH3CH2CHO
(2) CH3COCH3 CH=CHCOCH3
Re agent
(3) CH3CH2COCH3   
HO
(4) CH3CHO
CH=CHCH2CH3
40. The hydrocarbon which can react with sodium in
liquid ammonia is [A IEEE -200 8] HO

(1) CH3CH2CH 2C  CCH2CH 2CH 3 (1) NaBH 4

(2) CH3CH2C  CH (2) NH2 NH2, OH
(3) CH3CH=CHCH 3 (3) Zn – Hg / HCl
(4) CH3CH 2C  CCH2CH 3 (4) Na, Liq.NH 3

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 Page 97 HYDROCARBION - JEE

47. The hydration of propyne results in formation of :- CCCH3

[AIEE E - 2 01 2 (On li ne )]
51. In the given reaction H  / Hg2 
(1) Propanol–1 (2) Propanal
  A the
(3) Acetone (4) Propene product 'A' is :- [ A I E E E - 2 0 1 2 ( On l i n e ) ]
48. Consider the following sequence of reactions:
O
CH3CH=CH2
Cl 2 Na2CO3 (i) HOCl
A 420K, 12 atm B (ii) NaOH C ||
700K HO–C=CHCH 3 CH2–C–CH3
compound 'C' is :- [ A I E E E - 2 0 1 2 ( On l i n e ) ]
(1) (2)
(1) CH2OH (2) CH3CHCOCl
CHOH OH
CH2OH OH
|
(3) HOCH 2–CH=CH 2 (4) CH3CHCOONa O=C–CH2CH3 HC=C–CH3
OH
49. The major product obtained in the photobromination (3) (4)
of 2-methyl butane is :- [ A I E E E - 2 0 1 2 ( On l i n e ) ]
(1) 2-bromo-3-methylbutane
(2) 1-bromo-2-methylbutane 52. A gaseous hydrocarbon gives upon combustion
(3) 1-bromo-3-methylbutane 0.72 g of water and 3.08 g of CO2. The empirical
(4) 2-bromo-2-methylbutane formula of the hydrocarbon is [JEE(MAIN)-2 0 1 3 ]
50. The reaction, [ A I E E E - 2 0 1 2 ( On l i n e ) ] (1) C2H 4 (2) C3H 4 (3) C6H 5 (4) C7H 8
[ H]
CH3CHO  Zn (Hg ) / Conc.HCl
 CH3CH3 is :-
(1) Cannizaro's reaction
(2) Wolf-Kishner reduction
(3) Rosenmund reduction
(4) Clemmenson reduction

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HYDROCARBION - JEE Page 98

ANSWER KEY
EXERCISE - I
Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s 1 3 4 2 2 1 2 1 2 3 2 1 1 2 2
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
An s 2 1 4 4 3 3 3 3 4 4 2 2 3 4 4
Que. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
An s 1 3 4 2 1 4 2 2 1 2 3 2 1 1 2
Que. 46 47 48 49 50 51 52 53 54
An s 2 2 3 2 2 4 1 3 1

EXERCISE - II

Qu e . 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s 3 2 3 4 4 1 2 3 4 3 1 1 3 2 2
Qu e . 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
An s 3 3 4 4 2 3 1 3 3 1 1 3 1 3 1
Qu e . 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
An s 1 1 3 1 1 2 1 2 3 1 4 2 3 1 3
Qu e . 46 47 48 49 50
An s 2 3 3 1 3

EXERCISE - III
Q u e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans 3 1 1 1 2 4 2 1 4 3 2 3 2 4 1
Q u e. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans 3 1 2 1 1 2 1 3 1 3 1 4 1 3 1
Q u e. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
Ans 1 2 4 2 1 3 4 3 4 2 4 4 4 4 3
Q u e. 46 47 48 49 50 51 52
Ans 2 3 1 4 4 3 4

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