II Hydrocarbon Alkene

AtoZ CHEMISTRY Hydrocarbon – Alkene
Hydrocarbon – Alkene
5. Preparation of Alkene – Part 1 O Me
Q 1. In the reaction Ph – C – C – Me Ph Me
CH3 − CH2 − CH2 − CH2 − OH C=C
(A) Ph (B) Ph Me
Conc. H2SO4
⎯⎯⎯⎯⎯⎯ → Major product, is O Ph
(A) CH3 − CH2 − CH = CH2 CH3 – C – C – Ph
(B) CH3 − CH = CH − CH3
(C) CH3 (D) None of these
CH3 – C = CH2
Q 6. In the reaction
CH3 CH3
(C)
OH
(D) CH3CH2CH 2CH3 CH3
Conc.H2SO4
Q 2. In the reaction OH ⎯⎯⎯⎯⎯⎯ → Major product ,
CH3 is
Conc H2SO4
CH3 CH3
OH
Major product, is
CH3 CH2 (A) CH3 (B) CH3
O
O
(A) (B) C – CH3
CH3 CH3 C
CH3
CH
(C) (D)
(C) (D)
Q 7. Which one of the reactant is best to prepare
Q 3. Hydrolysis of Alcohol produces ether CH3
(A) by intermolecular dehydration
(B) At low temperature CH3 – CH – CH = CH2 an action of alcoholic
(C) At high concentration of dehydrating agent KOH?
(D) All of these Br
Conc. H2SO4 CH3 – CH – CH – CH3
(CH3)2 C – C (CH3)3 CH3
(A)
Major product is Br
(A) (CH3)2 C = C (CH3) 2
CH3 – C – CH2 – CH3
O
(B) CH3
(B) (CH3 – C – C (CH3)3 CH3 – CH – CH2 – CH2Br
CH3 CH3 CH3
(C)
(C) H2C = C – C = CH2 (D) None of these
(D) None of these Q 8. The product formed in the reaction
Br Br Zn/
Ph Ph
Conc. H2SO4
Ph – C – C – Me  (A) (B)
OH OH
Major product, is
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Br
(C) (D) None of these
Q 9. The product formed in the reaction
Zn /  (C) (D)
Br − CH2 − C  C − CH2 − Br ⎯⎯⎯→
(A) H 2C = C = CH 2 (B) CH3 − C  C − CH3 Q 13. The acid catalyzed dehydration of the alcohol
C  C shown below gives a major product which results
from a carbocation rearrangement. Identify this
(C) CH2 – CH2 (D) None of these major product
Q 10. In the dehydration of , the products

formed are
(A) (B)
(A) (B)
(C) (D)
(C)
(D) All the three products are formed

Q 14.
OH
(i) H+ Major product is
(ii) –H2O Product, is
(A) (B)
(A) (B)
(C) (D)
(C) (D) Q 15. Which of the following will be the correct
product (P) for the given reaction ?
Q 12. product (P). P would be
(A) (B) (A) (B)

(C) HCl  HBr  Hf  HCl

(D) None of these
Q 5. Predict which of the following alkenes reacts the
(C) (D) fastest with HCl?
(A) CH3CH2CH2CH2CH = CH2
(B) Trans - CH3CH2CH = CHCH 2CH3
Q 16. (C) Cis − CH3CH2CH = CHCH2CH3
(D) ( CH3 ) C = CHCH2CH3
2
Q 6. Which one of the following compounds is most
(A) (B) reactive towards addition of HBr?
(A) CH2 = CH2 (B) CH3 − CH = CH2
(C) CH3 − CH = CH − CH3
(C) (D)
(D)
Q 7. The order of reactivity of the following alkenes
towards electrophilic attack is
(i) CH3CH = CH 2 (ii) CH2 = CHCOOH
6. Preparation of Alkene – Part 2

Q 1. Ease of dehydration among the following (iii) CH2 = CH2 (iv)
molecules (A) i  iii  iv  ii (B) i  iii  ii  iv
CH3 – CH2 – CH2 – OH
(C) iv  i  iii  ii (D) i  iv  iii  ii
I Q 8. Correct order of Heat of hydrogenation
CH3
CH3 – C – OH CH3 – CH – CH2 – CH3
CH3 OH
II III
(A) I  II  III (B) III  II  I
(C) II  III  I (D) I  III  II
Q 2. Alkene is
(A) Lewis acid (B) Lewis base
(C) Amphoteric (D) Both A & B (A) I  II  III  IV (B) III  IV  I  II
Q 3. Which alkene has a pleasant smell ? (C) II  III  IV  I (D) None of these
(A) butylenes (B) propene Q 9. The maximum heat of hydrogenation of the given
(C) Ethylene (D) decene compound is
CH3 − CH = CH 2 + HX → CH3 − CH − CH3
X (A) (B)
The reactivity order of HX is
(A) HF  HCl  HBr  HI
(B) HI  HBr  HCl  HF
(C)
(C) (D) (D) None of these
Q 10. What is the major product of the following
Reaction ?
Q 13. Which of the given reaction follows the Anti –
Markownikov’s rule for finding the major
product ?
(A) (B)
(A)
(C) (D)
(B)
Q 11. The reaction of
(C)
with HBr gives
(A) (D)
(B)
Q 14. Product
How many products will be formed in above
(C) Reaction?
(A) 2 (B) 4 (C) 6 (D) 5
Q 15. The intermediate formed during the addition of
(D) HCl to propene in the presence of peroxide is
Q 12. Which of the following is the correct major + •
product of the given reaction? (A) CH3CH 2 C H 2 (B) CH3 C HCH3
• +
(C) CH3CH 2 C H 2 (D) CH3 C HCH3
Q 16. The major product in the reaction
CH3
CBrCl3
Product
R2O2
(A) CCl3 CH3
CH3 Br
(A) Br (B) CCl3

CH3 CH3
(B) CBrCl2 Cl
(C) Cl (D) CBrCl2

7. Properties of Alkene
Q 1. Rank the following in order of decreasing
reactivity with bromine, Br2
Q 5. Which of the following alkenes gives 1-bromo-2-

methyl-2-pentanol upon reaction with Br2/H2O?
(A) CH3CH = CHCH ( CH3 )
(1) (2) (3)
(A) 1  2  3 (B) 2  3  1 2
(C) 3  1  2 (D) 3  2  1 (B) CH3CH2CH = C ( CH3 )
2
Q 2. Give the product of the following reaction
(C)
(D)
(A)
Q 6.
(B) and its mirror image
(C) Both A and B are formed
(D) None of these
Q 3. (A) (B)
A and B would be respectively
(A) (C) (D)

Q 7. The reaction of propene with HOCl (Cl2+ H2O)
proceeds through the intermediate
(A) CH3 − CH + − CH 2 − Cl
(B)
(B) CH3 − CH ( OH ) − CH2+
(C) CH3 − CHCl − CH +2
(C) (D) CH3 − CH + − CH 2 − OH

Q 8. Identify the product, P in the following reaction
CH3 − CH = CH2 + NOCl → P
(D)
Q 4. Identify number of chiral centers present in (A) (B)
product obtained by following reaction

(C) (D)
Q 9. What is (are) the major product(s) of the
following reaction ?
(A) (B)
(A)
(C) (D)
(B) (C)
(D) Both A and B Q 13.
Q 10.
A and B are
(A) (B)
(A)
(B) (C) (D)
(C) B2D6

H2O2, OH
Q 14.
(D)
Q 11.
(A) (B)
(A) (B)
(C) (D)
(C) (D)
Q 12. Draw the product of following reaction with
Stereochemistry?
Q 15.

A, which is true about this reaction ?

(A) A is meso 2, 3-butan –di-ol formed by syn
addition
(B) A is meso 2,3-butan –di-ol formed by anti
(A) (B)
addition
(C) A is a racemic mixture of d and 1,2,3-butan-
di-ol formed by anti addition
(D) A is a racemic mixture of d and I2,3- butan –
(C) (D) di-ol formed by syn addition
Q 4.
A→ B ⎯⎯⎯⎯
CH3 − C  C − CH3 ⎯⎯⎯
cold aq. 
→
 KMnO4 
8. Reaction of Alkenes
Q 1. Which reaction proceeds by anti addition? A and B would be respectively
(A) H2 / Pd − BaSO4 / Quinoline,
CH3 − CH = CH − CH3 ( cis )
(A)
(B) H2 / Pd − BaSO4 / Quinoline,
CH3 − CH = CH − CH3 ( Trans )
(B)
(C) Na / liq.NH3 , CH3 − CH = CH − CH3 ( cis )
(D) Na / liq.NH3,CH3 − CH = CH − CH3 ( Trans )
(C) Q 5. CH3 − C  C − CH3 ⎯⎯⎯
A
→  B ⎯⎯⎯⎯
3 → RCO H
H 2O
(D)
A and B would be respectively

Q 2. H2 / Pd − BaSO4 /
(A) Quinoline,
R1 and R 2 are
CH3 − CH = CH − CH3 ( cis )
(A) Cold alkaline KMnO4 ,OsO4 / H2O2
H2 / Pd − BaSO4 /
(B) Cold alkaline KMnO4 ,HCO3H (B) Quinoline,
(C) Cold alkaline KMnO4 ,CH3 − O − O − CH3 CH3 − CH = CH − CH3 ( Trans )
(D) C6H5CO3H, HCO3H Na / liq.NH3 , CH3 − CH = CH − CH3 ( cis )
(C)
Na / liq.NH3,CH3 − CH = CH − CH3 ( Trans )
(D)
Q 3. Q 6.
The probable structure of ‘X’ is CH3 – CH – CH2OH

(B) 18 OH
CH3 – CH – CH2OH
(C) OH
(A) (B) (D) None of these
RCO3H
CH3 – CH = CH2
CH3O¯ Na+ Product, is
OH
(C) (D)
(A) CH3 – CH – CH2OCH3
CH3 – CH – CH2OCH3
Q 7. (B) OCH3
Identify ‘X’ OH
CH3 – CH2 –CH
(C) OCH3
(D) None of these
(A) Q 11. In the reaction
Cl2
A
500°C
CH3 – CH = CH2
Cl2/CCl4
B
Room temp
(B)
A & B are respectively
CH3 – CH – CH3 Cl & CH3 – CH – CH2Cl
(A) Cl Cl
Cl – CH2 – CH = CH2 & CH3 – CH – CH2Cl
(C)
(D) Reaction will not occur (B) Cl
Q 8. In the reaction Cl – CH2 – CH – CH2 Cl & CH3 – CH – CH2Cl
CH3 H (C) Cl Cl
C=C + RCO3H CH3 – CH – CH2Cl & Cl – CH2 – CH = CH2
H CH3 Product, (D) Cl
The product formed is
(A) Meso (B) d − pair Q 12.
(C) single product (D) None of these major product, (A) A would be
RCO3H
CH3 – CH = CH2 (A)
H/H2O18 Product, is
18 (B)
CH3 – CH – CH2OH
(A) OH (C)

(d) Two moles O=CHCH2CH=O

(e) O=CHCH2CH2CH2CH=O
(D) Q 2. Write the structure of the substrate molecule
-
(A) C7H14 1.KMnO4 /OH / CH CH COOH+CH CH CH -COOH
+ 2.H 3 2 3 2 2
Q 13. Product (A), A would not be Write the structure of C 7H14
-
(B) C10 H16 1.KMnO4 /OH /
HOOC-CH2CH2-CH2-COOH(only)
2.H+
Write the structure of C10 H16
O
(A) (B) -
(C) C10 H16 1.KMnO4 /OH / +HOOC-CH2-CH2-COOH
2.H +
O
Write the structure of C10H14
-
(D) C10 H14 1.KMnO4 /OH /
2.H+ O
(C) (D)
HOOC-CH2-CH2-CH2-C-C-CH2-CH2-CH2-COOH
O
Write the structure of C10H14
O
C
1.O3
(E) Alkene CH3 CH3 +CH3-CH-CHO
Q 14. 2.Zn/H2O
Write the structure of Alkene CH3
Q 3.
(A)
A B
(C6 H12 ) (C6 H12 )
1.O3 1.O3
2.Zn/H2O 2.Zn/H2O
Acetone Only CH3-CH2CHO Only
(B) Write the structure of A & B.
Q 4.
O O
1.O3
O
C11H16 C
2.Zn/H2O +CH3 CH3 +CH2O
(C)
O
(D) None of these Write the structure of C11H16
Q 5. Alkene A
O
O3/H2O
CH3 – C – CH3 + CH3COOH+CH3 – C – COOH
9. Ozonolysis & Oxidation of Alkene
Q 1. Write structural formulas for the compounds O
which yield the following products on reductive A can be
ozonolysis CHCH3
(a) Two moles of O=C(CH3)CH2CH3 CH3
(b) (C2H5)C=O + O=CHCH=O + O=CHCH2CH3 CH3 – C – CH = C
(A) CH3
(c) H2C=O+O=CHCH(CH3)CH(CH3)2
C(CH3)2
(B) CH3 – C – CH = HC – CH 3 (D)

(C) Both correct Q 10. The treatment of
(D) None is correct
Q 6. Ozonolysis of CH3 − CH = C = CH2 will give
with KMnO 4 / H + produces
(A) Only CH3CHO
(A) CH3COCH3 + CH2O
(B) Only HCHO
(C) Only CO 2 (B) CH3COCH3 + CH3COOH
(D) Mixture of CH3CHO,HCHO & CO2 (C) CH3CHO + CO2
Q 7. O-xylene on ozonolysis will give (D) CH3COCH3 only
O Q 11. One mole of a symmetrical alkene on ozonolysis
CHO
& CH3 – C – CHO gives two moles of an aldehyde having a
(A) CHO molecular mass of 44 u. The alkene is
O (A) propene (B) 1-butene
CH3 – C = O (C) 2-butene (D) ethene
& CH3 – C – CHO Q 12. Which compound would give 5-keto-2-methyl
(B) CH 3 – C = O
hexanal upon ozonolysis ?
CH3 – C = O CHO
&
(C) CH3 – C = O CHO
O
CH3 – C = O CHO
, CH3 – C – CHO &
(D) CH3 – C = O CHO (A) (B)
Q 8.
What would be A
(C) (D)
(A) (B) Q 13. Which of the following compounds on reductive
ozonolysis give ( CH3 ) CO,CHO − CO − CH3
2
and CH3CHO ?
(C) (D) None of these
Q 9. Which of the given compound given CO 2 gas
after treatment with hot, alk. KMnO4 (A)
(A) CH3 − CH = CH − CH3
(B) CH3 − C  C − CH3 (B)
(C)
(C)

Q 3. But-2-ene can be obtained by reacting

(A) 1,2-dibromopropane with zinc
(B) ethyl bromide with sodium
(D) (C) ethylidene bromide with zinc
Q 14. Baeyer’s reagent is [IIT JEE 1984] (D) n-butyl alcohol with alcoholic KOH
(a) alkaline permanganate solution Q 4. In the following reaction,
(b) acidified permanganate solution
(c) neutral permanganate solution
(d) aqueous bromine solution
Q 15. An organic compound ‘A’, C8H12, on
reaction with ozone followed by Zn gave one The major product is
mole each of (CHO)2 and CH3COCH3, The
structure of ‘A’ is
(A)
(B)
(C)
(D)
Q 5. Ozonolysis of an organic compound gives
formaldehyde as one of the products. This
confirms the presence of
10. Ozonolysis & other Reactions of Alkene (A) a vinyl group
Q 1. The maximum number of isomers for an alkene (B) two ethylenic double bonds
(C) an isopropyl group
with molecular formula C4H8 is
(D) an acetylenic triple bond
(A) 2 (B) 3 (C) 4 (D) 5 Q 6. Identify (B) and (D) in the following sequence of
Q 2. Products of the following reaction, reactions
(i) O
Me2C = CHCH3 ⎯⎯⎯⎯⎯⎯
3 → ? are : 2 4 → ( A ) ⎯⎯⎯
conc. H SO
H2C = CH2 ⎯⎯⎯⎯⎯⎯ 2 →(B) H O
(ii) ( CH3 ) S 
2
(A) Me2CO + CH3CHO ( D)
(B) ⎯⎯⎯ ( )
PBr
3 → C ⎯⎯⎯
→ H 2C = CH 2
(B) CH3CHO + CH3COOH (A) CH3OH and C2H5Br
(C) Me2CO + CH3COOH (B) C2H5HSO4 and alc. KOH
(D) 2Me2CO (C) C2H5OH and alc. KOH

(D) C2H5HSO4 and aq. KOH (B) 1-phenyl-2-propanol

Q 7. The olefin which on ozonolysis gives (C) 2-phenyl-2-propanol
(D) 2-phenyl-1-propanol
CH3CH2CHO and CH3CHO is
Q 14. Reaction of one molecule of HBr with one
(A) 1-butene (B) 2-butene molecule of 1,3-butadiene at 40°C gives
(C) 1-pentene (D) 2-pentene predominantly
Q 8. Anti-Markownikoff addition of HBr is not (A) 3-bromobutene in kinetically controlled
observed is (B) 1-bromo-2-butene in thermodynamically
(A) propene (B) 1-butene Controlled conditions
(C) 2-butene (D) 2-pentene (C) 3-bromobutene under thermodynamically
Q 9. Ozonolysis of the following compound controlled conditions
(D) 1-bromo-2-butene in kinetically controlled
Q 15. An alkene on reductive ozonolysis gives two
gives
molecules of CH 2 ( CHO )2 . The alkene is
(A) 2,4- hexadiene
(B) 1,3-cyclohexadiene
(A) (B) (C) 1,4-cyclohexadiene
(D) 1-methyl-1,3-cyclopentadiene
(E) 1,2-dimethyl cyclopropene
(C) (D) Q 16. HBr reacts with H2C = CH − OCH3 under
Q 10. In presence of peroxide, hydrogen chloride and
hydrogen iodide do not give anti-Markownikoff’s anhydrous conditions at room temperature to give
addition to alkenes because (A) CH3CHO and CH3Br
(A) both are highly ionic (B) BrCH2CHO and CH3OH
(B) one is oxidizing and other is reducing
(C) BrCH2 − CH2 − OCH3
(C) one of the steps is endothermic in both cases
(D) all the steps are exothermic in both the cases (D) H3C − CHBr − OCH3
Q 11. But-1-ene may be converted to butane by a Q 17. The products obtained by the ozonolysis of 2-
reaction with ethyl but-1-ene are
(A) Zn-HCl (B) Sn-HCl (A) ethanal and propanone
(C) Zn-Hg (D) Pd/H2 (B) ethanal and butanal
Q 12. Which of the following alkenes will give an (C) ethanal and 3-pentanone
optically active alcohol when treated with (D) methanal and 2-pentanone
H 2O / H 2SO4 ? (E) methanal and 3-pentanone
(A) 1-Butene (B) Ethene
(C) Propene (D) 2-Methylpropene
Q 13. The product of acid catalysed hydration of 2-
phenyl propene is
(A) 3-phenyl-2-propanol

Answer Key
CH3
H2C = CH – CH – CH
CH3
5. Preparation of Alkene – Part 1 (c) CH3
(1). B (2). C (3). D CH = CH
(4). B (5). C (6). D CH2 CH2
(7). C (8). B (9). A (d) CH = CH
(10). D (11). C (12). A
(13). A (14). B (15). C
(e)
(16). D
(2).
6. Preparation of Alkene – Part 2
(a) CH3 – CH2 – CH = CH – CH2 – CH2 – CH3
(1). C (2). B (3). C
(4). B (5). D (6). D
(7). C (8). C (9). A (b) (c)
(10). C (11). B (12). C
(13). B (14). B (15). D (d)
(16). B CH3
C = CH – CH3
7. Properties of Alkenes (e) CH3
(1). A (2). B (3). C
(4). 3 (5). D (6). B (3).
(7). A (8). B (9). B CH3 CH3
(10). A (11). D (12). C C=C
(13). A (14). C (15). A (a) CH3 CH3
(16). A (b) CH3 – CH2 – CH = CH – CH2 – CH3
8. Reaction of Alkenes H3C CH3

(1). A (2). B (3). A CH2
(4). A (5). A (6). A
(7). B (8). B (9). B
(10). A (11). B (12). A
(13). D (14). C (4). CH3 CH3
(5). C (6). D (7). D
9. Ozonolysis & Oxidation of Alkene (8). B (9). D (10). B
(11). C (12). B (13). B, C
(1).
CH2 – CH3 (14). A (15). D
CH3 – CH2
C=C
CH3 CH3 10. Ozonolysis & other Reactions of Alkene
(a)
C2H5 (1). C (2). A (3). C
C = CH – CH = CH – CH2CH3 (4). B (5). A (6). C
(b) C2H5 (7). D (8). C (9). B
(10). C (11). D (12). A
(13). C (14). B (15). C
(16). D (17). C


II Hydrocarbon Alkene

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II Hydrocarbon Alkene

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AtoZ CHEMISTRY Hydrocarbon – Alkene

Q 10. In the dehydration of , the products

Q 11. In the reaction

Q 12. product (P). P would be

(A) (B) (A) (B)

Rishi Sir [B.Tech. IIT Kanpur] www.atozchemistry.com 116

(C) HCl  HBr  Hf  HCl

6. Preparation of Alkene – Part 2

(A) Br (B) CCl3

(C) Cl (D) CBrCl2

Rishi Sir [B.Tech. IIT Kanpur] www.atozchemistry.com 118

Q 5. Which of the following alkenes gives 1-bromo-2-

(A) (C) (D)

(C) CH3 − CHCl − CH +2

(C) (D) CH3 − CH + − CH 2 − OH

Rishi Sir [B.Tech. IIT Kanpur] www.atozchemistry.com 119

(B) (C) (D)

Rishi Sir [B.Tech. IIT Kanpur] www.atozchemistry.com 120

A, which is true about this reaction ?

A and B would be respectively

The probable structure of ‘X’ is CH3 – CH – CH2OH

Rishi Sir [B.Tech. IIT Kanpur] www.atozchemistry.com 122

(d) Two moles O=CHCH2CH=O

(B) CH3 – C – CH = HC – CH 3 (D)

Rishi Sir [B.Tech. IIT Kanpur] www.atozchemistry.com 124

Q 3. But-2-ene can be obtained by reacting

Rishi Sir [B.Tech. IIT Kanpur] www.atozchemistry.com 125

(D) C2H5HSO4 and aq. KOH (B) 1-phenyl-2-propanol

Rishi Sir [B.Tech. IIT Kanpur] www.atozchemistry.com 126

8. Reaction of Alkenes H3C CH3

Rishi Sir [B.Tech. IIT Kanpur] www.atozchemistry.com 127

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