Chemistry

CHECK YOUR GRASP HYDROCARBON EXERCISE-I

1. Petroleum mainly contains 8. Isobutylene react with HOCl gives

(1) Mixture of alkanes

OH
(2) Mixture of esters
(1) CH3 C CH2Cl
(3) Mixture of aromatic compounds
CH3
(4) Mixture of olefines

2. The reaction CH2 CH 2+H 2  Ni


250  300  C
CH3
CH3—CH3 is called
(2) CH3 C CH2OH
(1) Wurtz reaction
Cl
(2) Kolbe's reaction
(3) Sabatier - Senderens reaction (3)CH3 CH CH2OH
(4) Cabylamine reaction CH2 Cl

3. A compound responds to Baeyer's test but does (4) CH3 C O + CH3Cl

not give white precipitation when treated with
ammonical silver nitrate solution the compound CH3
should be
(1) C2H6 (2) C3H4 9. On heating sodium propionate with sodalime the
hydrocarbon obtained is
(3) C2H2 (4) C2H4
(1) Butane (2) Ethane
4. Pyrolysis of ethyl acetate gives (3) Propane (4) Ethene
(1) CH3COCH3 (2) CH2 CH2
(3) CH2 C O (4) CH 3—CHO 10. If the products of ozonolysis are acetone and
formaldehyde, what is the initial compound?
5. When CH3—CH CHBr reacts with HBr in
presence of peroxide the product will be (1) CH3 C C CH3 (2)CH3 C C H
(1) CH 3—CH 2—CHBr 2 CH3 CH3 CH3 CH3
Br Br
(3) CH3 C C H (4) CH3 C CHC2H5
(2) CH3 CH CH2
CH3 H CH3
(3) CH2 CH2 CH2

Br Br 11. What is the product of the reaction -

(4) CH3—CBr 2—CH 3 CH 2 CH(CH 2)6—CH3 
peroxide
?
HBr

6. In the formation of alkene when alcoholic KOH

reacts with CH3CH2Cl what is the attacking species (1) CH3 CH (CH2)6 CH3
in the reaction. Br
(1) C2H5O1 (2) OH1
  (2) CH2 CH2 (CH2)6CH3
(3) H 3 O (4) K
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) Br
(1) 40 g (2) 80 g
(4) None of above
(3) 160 g (4) 120 g
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 12. Review the following reactions and choose those 18. Tollen's reagent is
reactions which are completed by free radical (1) Ammonical cuprous chloride
mechanism (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) CH3—CH CH 2 
Peroxide  CH 3 CH 2 CH 2 Br AgNO3 solution are
CH 2 N2
(c) CH3—CH CH2 
 CH3 CH CH3 (1) CH3 CH C CH (2) HC CH
CH2 CH3
h
(d) CH4+Cl2   CH3Cl +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
(2) C C < C C < C—C CaC2 H2 O
  A 
dilH SO
 B 
Ni
H
C
2 4 2

(3) C C < C C < C—C

the product C is
(4) C C < C—C < C C
(1) CH3—OH (2) CH3CHO
14. Lindlar's catalyst is (3) C2H5OH (4)C2H4
(1) Pt in ethanol (2) Pd + CaCO3
21. In the reaction
(3) Ni in ethanol (4) Na in liquid NH3
CH 3 —C C—CH 3  (i)X
(ii)H 2 O / Zn

CO  H O
15. The reaction : CH3—CH CH2 
H
2

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 s
i
(1) Glyoxal (2) Chlorohydrin
KMnO 4
CH 3 CH CH 2 + H 2O + [O] 
Acid
 (3) Dichloro acetaldehyde (4) Formic acid

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

CH CH2  X + HCOOH
[O ]
CH3 X is:-
lene on
OH OH (1) COCl2 (2) SOCl2 (3) AsCl3 (4) AlCl3
24. Olefin, which gives CH3CHO and CH3CH2CHO
(1) CH3CH2COOH (2) CH3COOH
on ozonization and hydrolysis is:
(3) CH3CH2CHO (4) CH3CH2OH (1) 1–butene (2) 2–butene
(3) 1–pentene (4) 2–pentene
17. Addition of two molecules of HBr to CH3—C CH
gives 2
Hg CH 3 MgX / H 2 O
25. CH CH 
H SO
 B   C 
[O ]

2 4
(1) CH3—CBr2—CH3 (2) CH3 CH CH2
D End product D will be
Br Br
(1) Acetaldehyde
(3) CH3—CH2—CHBr2 (4) CH3 CH2 CH2 (2) Isopropyl alcohol
(3) Ethyl alcohol
Br Br
(4) Acetone
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Chemistry
26. Which of the following molecule shows dipole 32. What is the product formed when 1-butene is heated
moment with Al2(SO4)3 at 500K
(1) 2, 2–dimethyl propane (1) CH3CH2CH2CH3
(2) Trans -2 - pentene (2) CH2 CH—CH CH2
(3) Trans 3– Hexene
(3) (CH3)2C CH2
(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 KMnO4 forms
(1) 1-butene (2) 2-butene
(1) CH2 CH2 (2) Oxalic acid
(3) Iso butene (4) Butyne
(3) CH3COOH (4) CO2 + H2O
29. Which of the following give H2 gas with Na
35. The compound on ozonolysis and followed by
(1) CH4 (2) C2H6
reduction gives two mole of acetaldehyde. The ‘X’
(3) C2H4 (4) C2H2
s
i
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 AgNO3 (4) NaHSO3
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) C2H6 (2) C2H4
(3) C4H10 (4) C2H5Cl

66 E
 40. Which reagent converts propene to 1–propanol 47. The treatment of benzene with isobutene in the
(1) H2O, H2SO4 presence of sulphuric acid gives
(2) B2H6, H2O2, OH –
(1) I sobut yl benzene. (2) t –but yl benzene.
(3) Hg(OAc)2,NaBH4/H2O
( 3) n–But yl benzene (4) No react i on.
(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) CH3CH2CH(OCH3)CH3
(3) Trans– 2–butene > Cis– 2–butene > 1–butene
(2) CH3CH CHCH3
(4) Cis–2 butene > Trans– 2–butene > 1–butene
(3) CH3CH2CH CH2
42. CH3 CH2 CH CH3 obtained by chlorination of (4) CH3CH2CH2CH2OCH3
Cl
49. 3–Phenyl propene on reaction with HBr gives (as
n–butane, will be
(1) Meso form (2) Racemic mixture a major product)

(3) d–form (4) –form (1) C6H5CH2CH(Br)CH3

43. Which alkene on ozonolysis gives CH3CH2CHO (2) C6H5CH(Br)CH2CH3
(3) C6H5CH2CH2CH2Br
and CH3CCH3
(4) C6H5CH(Br)CH CH2
O CH3
(1) CH3CH2CH C 50. Products of the following reaction
CH3
(1 ) O
C.CH2CH3   
3
(2) CH3CH2CH CHCH2CH3 CH3C (2) Hydrolysis are
(3) CH3CH2CH CHCH3
(1) CH3COOH + CH3COCH3
(4) CH3 C CHCH3
(2) CH3COOH + HOOC.CH2CH3
CH3
(3) CH3CHO + CH3CH2CHO
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
iscalled
(1) t–butyl chloride (2) Sec. butyl chloride
(3) Iso butyl chloride (4) n–butyl chloride (1) Cope reduction
(2) Dow reduction
45. When CH3CH2CHCl2 is treated with NaNH2, the
(3) Wolf-kishner reduction
product formed is :
(1) CH3—CH CH2 (2) CH3—C CH (4) Clemmensen reduction

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

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

The compound CH3 C (84%)

46. 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) CH3COCH3 + CH3COOH
(3) CH3COCH3 + CH3CHO (4) CH4 + LPG
(4) CH3CHO + CO2 (10%) (90%)

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Chemistry

53. 2-Bromopentane is heated with potassium ethoxide 54. Which of the following acidity order is correct -
in 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

CHECK YOUR GRASP ANSWER KEY EXERCISE-I

Que . 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans 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
Ans 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
Ans 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
Ans 2 2 3 2 2 4 1 3 1

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 BRAIN TEASERS HYDROCARBON EXERCISE-II

1. The smallest alkane which can show optical 6. Monochlorination of ethylbenzene (PhCH2CH3)
isomerism possesses - with Cl2 under heat produces -
(1) 5 carbons (2) 6 carbons (1) PhCH2CH2Cl
(3) 7 carbons (4) 8 carbons (2) PhCHClCH3
(3) both (1) and (2) in equal amounts
2. The appropriate reagent for the transformation (4) more of (2) and less of (1)
O
7. The least reactive alkane towards free-radical
CH3
is- substitution reactions is-
HO HO (1) CH4 (2) (CH3)3CH
(1) Zn(Hg)/HCl (2) NH2NH2,OH– (3) CH3CH3 (4) CH3CH2CH3
(3) H2/Ni (4) NaBH4 8. Raney nickel, which is used as a catalyst, is
obtained by-
3. Ethylmagnesium bromide reacts with methanol (1) grinding solid nickel
to produce - (2) by treating nickel–aluminium alloy with dilute
(1) methane (2) methoxyethane NaOH
(3) ethane (4) propane (3) by treating nickel–aluminium alloy with dilute
HCl
4. An aqueous mixture of sodium ethanoate and (4) by heating nickel tetracarbonyl
sodium propanoate is electrolyzed. The product
of the reaction is- 9. Consider the following reaction-
C H 3 C H = C H 2 
1.BH 3

(1) CH3CH2CH3 (2) CH3CH2CH2CH3 2 .CH 3 COOH

The product formed is

(3) CH3CH3 (4) all of these
(1) CH3CH2CH2OH (2) CH3CH(OH)CH3

5. The relative reactivity of 1ºH, 2ºH and 3ºH in (3) CH3CH2CH3 (4) CH2–CH2
bromination reaction has been found to be
CH2
1 : 82 : 1600 respectively. In the reaction - 10. The major component of LPG is -
(1) methane (2) ethane
CH3
hv (3) propane (4) isobutane
CH3–CH–CH3 (excess) + Br2
11. The following conversion
CH3 CH3
CH3–C–CH3+CH3–CH–CH2–Br R R H
C=O C
Br R R H
(A) (B)
cannot be effected by
the percentage yields of the products (A) and (B)
(1) Clemmensen reduction
are expected to be -
(2) Wolff-Kishner reduction
(1) 99.4%, 0.6% (2) 50%, 50%
(3) Wurtz reaction
(3) 0.6%, 99.4% (4) 80%,20% (4) Red P and HI at 200ºC

E 69
Chemistry
12. Which of the following halogen reacts with alkanes 18. Propene on reaction with Cl2 at 600º produces -
with explosive violence -
(1) 1, 2–dichloropropane
(1) F2 (2) Cl2
(2) 1–chloropropane
(3) Br2 (4)I2
(3) 3–chloropropene
13. The major product formed in the dehydration of (4) 2–chloropropene
1–butanol by heating with concentrated H2SO4
19. cis–2–Butene on reaction with Br2 in CCl4
is-
produces mainly -
(1) trans–2–butene (2) cis–2–butene
(3) 1–butene (4) 1, 3–butadiene (1) 1–bromo–2–butene
(2) 2,3–dibromobutane
14. For the reaction
(3) meso–2,3–dibromobutane
H2SO4
CH2OH (4) (±) 2,3–dibromobutane

the major product is 20. Which of the following reactions will result in the
formation of a chiral centre in the product -
(1) CH2 (2) CH3
(1) CH3CH=CH2+HBr 

(3) (4) (2) CH2=CH2+HOBr 

15. Propene is allowed to react with B2D6 and the (3) CH3CH2CH=CH2+HBr 
H2 O2

product is treated with acetic acid. The final

(4) CH3CH2CH=CH2+HBr 
product obtained is -
(1) 1–deuteriopropane 21. Propene on reaction with N–bromosuccinimide
(2) 2–deuteriopropane in CCl4 produces -
(3) 1–deuteriopropene
(1) 1, 2–dibromopropane
(4) 2–deuteriopropene
(2) 3–bromopropene
16. Ethylene reacts with Br2 to give (3) 1–bromopropene
1,2 dibromoethane. The anti-addition takes place
(4) 2–bromopropene
due to the formation of the intermediate-
+ 22. 1–Methylcyclohexene is allowed to react with
(1) CH2Br–CH2 (2) CH2– CH2 B2H6. The product is then treated with H2O2
+
Br and NaOH. The reaction is -

(3) BrCH=CH+ (4) CH2– CHBr 1.B2H6

+ 2.H2O2/ OH
–

Br
CH3

17. Propene on reaction with Br2 in CCl4 yields- The product formed is
(1) 1,2–dibromopropane (1) 1–methylcyclohexanol
(2) trans–1,2–dibromopropane (2) 2–methylcyclohexanol
(3) (±) 1,2–dibromopropane (3) (±) trans–2–methylcyclohexanol
(4) 3–bromopropane (4) (±) cis–2–methylcyclohexanol

70 E
 23. Which of the following alkyl halides undergoes 29. Consider the reaction
the fastest base–induced dehydrohalogenation CH3
+ – Heat
(1) t–Butyl iodide (2) t–Butyl bromide CH3CH2CH2–N–CH2CH3 OH

(3) Isobutyl bromide (4) s–Butyl iodide CH3

24. In the presence of a peroxide, which of the
following hydrogen halides undergoes addition
reaction with propene in an anti-Markovnikov
fashion
Which of the following is formed in major amount
(1) C H 2 = C H 2
(2) CH3CH2=CH2
(3) Both (1) and (2) in equal amount
(4) None, as no reaction takes place

(1) HF (2) HCl 30. The synthetic fibre orlon is prepared by the
(3) HBr (4)HI polymerization of -
(1) chloroethene (2) propene
25. Propene on reaction with ICl produces mainly - (3) propenenitrile (4) 2–chloro–1,3–butadiene
(1) 1–chloro–2–iodopropene 31. A hydrocarbon C6H10 absorbs only one molecule
(2) 2–chloro–1–iodopropane of H2 on catalytic hydrogenation. On ozonolysis,
the hydrocarbon yields CHO(CH2)4CHO. The
(3) (±)–2–chloro–1–iodopropane
hydrocarbon is -
(4) (±)–1–chloro–2–iodopropane (1) cyclohexene
(2) 1,5–hexadiene
26. cis–2–Butene on reaction with cold dilute KMnO4
(3) 1,3–cyclohexadiene
solution produces -
(4) 1–methylcyclopentene
(1) meso–2,3–butanediol (2) (±) 2,3–butanediol
(3) 2, 3–butanedione (4) 1,2–butanediol 32. In the addition of HBr to propene in the absence
of a peroxide, the first step involves the addition
27. Consider the following reaction of-
(1) H+ (2) Br–
CH 2 =CH 2  HOCH 2 –CH 2 OH
diluteKMnO 4
H 2 O,NaOH (3) H  (4) Br 

Which of the following statements is correct about 33. In the reaction

the procurement of two oxygens in the product ?
CH 3 CH 2CH=CH 2  
1.Hg(OAc )2 ,H 2 O
2.NaBD 4
(1) Both are procured from KMnO4
the product obtained is -
(2) Both are procured from H2O (1) CH3CH2CHOHCH2D
(3) Both are procured from NaOH (2) CH3CH2CHDCH2OH
(4) One is procured from KMnO4 and the other (3) CH3CH2CD(OH)CH3
from NaOH (4) CH3CH2CD2CH2OH

28. Which of the following will give the best yield of 34. The major product obtained in the reaction of
2–pentene on reaction with C2H5ONa/C2H5OH 1,3-Butadiene with HCl (1 mole) at a higher
temperature (100ºC or above) is
(1) 2–Iodopentane
(1) 3,4–dichloro–1–butene
(2) 2–Bromopentane
(2) 3–chloro–1–butene
(3) 3–Iodopentane (3) 1–chloro–2–butene
(4) Allequallysatisfactorily (4) 2–chloro–2–butene

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Chemistry

35. The major product formed by the addition of 41. The ease of formation of free radicals follows the
1 mole of HCl to 1,3-Butadiene at a low order -
temperature (0ºC or below) is  
(1) 3 º  2 º  1 º  C H 3 (2) C H 3  1 º  2 º  3 º
(1) 3–chloro–1–butene
 
(2) 1–chloro–2-butene (3) 1 º  2 º  3 º  C H 3 (4) 2 º  1 º  3 º  C H 3
(3) 2–chloro–2–butene
(4) Chlorocyclobutane 42. Which of the following has the lowest heat of
hydrogenation per mole -
36. An optically active hydrocarbon (X) on catalytic
(1) cis–2–Butene (2) trans–2–Butene
hydrogenation gives an optically inactive
compound (Y), C6H14. The hydrocarbon (X) is- (3) 1–Butene (4) 1,3–Butadiene
(1) 3–methyl–1–pentene
(2) 3–methyl–2–pentene 43. The reaction of 1–butene with HBr in the presence
of peroxide gives -
(3) 2–ethyl–1–butene
(4) 3–methylcyclopentene (1) 2–bromobutane (2) 1–bromobutane

(3) 1,1–dibromobutane (4) 1, 2–dibromobutane

37. trans–2–Butene is allowed to react with D2 in
the presence of nickel as catalyst. The product 44. The intermediate formed during the addition of
formed is- HCl to propene in the presence of peroxide is-
 
(1) (±)–2,3–dideuteriobutane (1) CH 3 C HCH 2 Cl (2) CH 3 CH 2 C H 2
(2) meso–2,3–dideuteriobutane  
(3) CH 3 C HCH 3 (4) CH 3 CH 2 C H 2
(3) 1,4–dideuterio–trans–2–butene
(4) 2,3–dideuteriobutane 45. The order of stability of the alkenes

38. The addition of HCl to 1–phenylpropene gives- R2C=CR2, R2C=CHR, R2C=CH2,

(1) C6H5CHClCH2CH3 I II II
(2) C6H5CH2CHClCH3
RCH=CHR, and RCH=CH2
(3) C6H5CH2CH2CH2Cl
IV V
(4) C6H5CH(CH3)CH2Cl
is-
39. The reduction of 4–octyne with H2 in the presence
of Pd/CaCO3 – quinoline gives- (1) I > II > III > IV > V
(1) trans–4–octene (2) I = II > III > IV > V
(2) cis–4–octene
(3) II > I > IV > III > V
(3) a mixture of cis–and trans–4–octene
(4) a completely reduced product C8H18 (4) V > IV > III > I > II

40. Which of the following alkanes gives only one 46. The reaction of RCH=CH2 with B2H6 followed
monochlorinated product- by oxidation with alkaline H2O2 gives -
(1) CH3CH2CH3 (2) CH3CH2CH2CH3
(1) RCH(OH)CH2OH (2) R–COCH3
(3) (CH3)4C (4) CH3(CH2)3CH3
(3) RCH2CH2OH (4) RCH2CHO

72 E
 47. The major product obtained by the treatment of 50. The product obtained in the reaction
propyne with aqueous H2SO4 in the presence of
CH3 H Br2
HgSO4 is - is
C=C
(1) propanal H CH3
(2) acetone CH3 CH3
(3) propanol H Br H Br
(1) (2)
(4) propyl hydrogen sulphate H Br Br H
CH3 CH3
48. The major product of the debromination of meso–
dibromobutane is-
(1) n–butane (2) 1–butene CH3 CH2Br
Br H H H
(3) trans–2–butene (4) cis–2–butene
(3) (4)
49. Which of the following will not react with an H Br H H
ammonical silver nitrate solution- CH3 CH2Br

(1) CH3CCH (2) (CH3)2CH–CH

51. The bond dissociation energies of the following
(3) CH3CCCH3 (4) HCCH
CH3–H CH3CH2–H CH2=CH–CH2–H C6H5–H
I II III IV
vary in the order
(1) I > II > III > IV (2) IV > III > II > I
(3) IV > I > II > III (4) II > I > IV > III

BIRAIN TEASERS ANSWER KEY EXERCISE-II

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

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Chemistry

PREVIOUS YEAR QUESTIONS HYDROCARBON EXERCISE-III

1. Alcoholic solution of KOH is a specific reagent for

7. In the compound CH2=CH–CH2–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 Screening-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 Screening-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
74 E
 13. Consider the following reactions -
OH  X
[IIT Screening-2002] 18. 
H

 
2Br
 5
H O
2 (Mixture )
H3C–CH–CH–CH3+Br 'X' + HBr
compounds of molecular formula C4H8Br2.No. of
D CH3 compounds X will be [IIT Screening-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 - [AIEEE-2003]
(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
[AIEEE-2003]
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 Screening-2002] by the reaction of - [IIT Screening-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
[AIEEE-2002] [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 - [AIEEE-2002]
[AIEEE-2004]
(1) CH3COCl (2) ClCH2CHO
CH3
(3) Cl2CHCHO (4) ClCH2COOH |
(1)CH3–CH2–CCH (2) CH3–CH2–CH–CH3

C6H5 – CC – CH3  A

HgSO 4
17. H 2 SO 4 H
|
[IIT Screening-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) C6H5–C=CHCH3 (4) C6H5–CH=C–CH3 (1) isobutane (2) 1–butyne

(3) 1–butene (4) n–butane
OH OH

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Chemistry
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–CH2–CH2–Cl
26. 2-Methylbutane on reacting with bromine in the (4) NO–CH2–CH2–CH2–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. 
Me OH
(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) CH2=CH2
(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 [AIEEE-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-
[AIEEE-05] dibromopropane [AIEEE-2007]
(1) predominantly 2–butene (1) CH3—C CH + 2HBr 
(2) equimolar mixture of 1 and 2–butene (2) CH3CH CHBr + HBr 
(3) predominantly 2–butyne (3) CH CH + 2HBr 
(4) predominantly 1–butene (4) CH3 — CH CH2 + HBr 

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 41. The treatment of CH3MgX with CH3C  C–H
36. The reaction of toluene with Cl2 in presence of
produces [AIEEE-2008]
FeCl3 gives predominantly-
(1) benzoyl chloride [AIEEE-2007] (1) CH3–CH=CH2 (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 :- [AIEEE-2010]
[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. The bromoalkane and alkyne
(3) deactivates the ring towards nucleophilic
respectively are – [IIT-2010]
substitution
(1) BrCH2CH2CH2CH2CH3 and CH3CH2CCH
(4) deactivates the ring towards electrophilic (2) BrCH2CH2CH3 and CH3CH2CH2CCH
substitution (3) BrCH2CH2CH2CH2CH3 and CH3CCH
(4) BrCH2CH2CH2CH3 and CH3CH2CCH
38. The compound formed as a result of oxidation of
44. Ozonolysis of an organic compound gives
ethyl benzene by KMnO4 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]

(1) Li AlH4 (2) Pt/H2

 A   B.
H2 O
CH3CH=CHCH3 
O3
Zn
(3) Li/NH3 (4) Pd/BaSO4
The compound B is 46. In the given transformation, which of the following
is the most appropriate reagent ? [AIEEE-2012]
(1) CH3CH2CHO
(2) CH3COCH3 CH=CHCOCH3

(3) CH3CH2COCH3  

Re agent

HO
(4) CH3CHO
CH=CHCH2CH3
40. The hydrocarbon which can react with sodium in
liquid ammonia is [AIEEE-2008] HO

(1) CH3CH2CH2C  CCH2CH2CH3 (1) NaBH4

(2) CH3CH2C  CH (2) NH2 NH2,OH
(3) CH3CH=CHCH3 (3) Zn – Hg / HCl
(4) CH3CH2C  CCH2CH3 (4) Na, Liq.NH3

E 77
Chemistry
47. The hydration of propyne results in formation of :- C CCH3
[AIEEE-2012(Online)]  2

(1) Propanol–1 (2) Propanal

51. In the given reaction 
H / Hg
A the
(3) Acetone (4) Propene product 'A' is :- [AIEEE-2012(Online)]
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 :- [AIEEE-2012(Online)]
(1) (2)
(1) CH2OH (2) CH3CHCOCl
CHOH OH
CH2OH OH
|
(3) HOCH2–CH=CH2 (4) CH3CHCOONa O=C–CH2CH3 HC=C–CH3
OH
49. The major product obtained in the photobromination (3) (4)
of 2-methyl butane is :- [AIEEE-2012(Online)]
(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)-2013]
50. The reaction, [AIEEE-2012(Online)] (1) C2H4 (2) C3H4 (3) C6H5 (4) C7H8
CH3CHO    CH3CH3 is :-
[ H]
Zn (Hg) / Conc.HCl

(1) Cannizaro's reaction

(2) Wolf-Kishner reduction
(3) Rosenmund reduction
(4) Clemmenson reduction

PREVIOUS YEAR QUESTIONS ANSWER KEY EXERCISE-III

Q ue . 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 ue . 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 ue . 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 ue . 46 47 48 49 50 51 52
Ans 2 3 1 4 4 3 4

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