M. P. I.

ALKENES XI & XII

ALKENES

1. Question : bring about the following conversions :

(1)

(2)

(3)

(4)

(5)

(6)

2. Write products
1 Me3 N  MeCl  Me4 N  Cl   Hoffmann Exhaustive methylation 
 2 Ph3 N  MeCl  No Re action dueto resonance
 3 Me3 P  MeCl  Me4 P Cl 
O
(4) Ph3P + MeCl Ph3PMeCl RLi Ph3P CH2
MeCHO
(5) Ph3P + Cl A B C

(6) PPh3 + O

O
(7) Ph3P + A B
O
(8) Ph3P + A B

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M. P. I. ALKENES XI & XII

Heat
(9) Ph3P + O

O
(10) Ph3P + MeCl A RLi B C
Heat
CHO
(11) Ph3P +
Br A RLi B Heat C

(12) Ph3P + Br A RLi B Heat C

O
O

(13) Ph3P + MeCl A RLi B C

Heat
O
PPh3 Se
(14) + A B
PPh3 Heat
O
R'2C C O

R'N C O
(15) Ph3P CR2
R'N O

R'2C NR

Question : Write products of the following with : Ph3P CH2 , Ph3P CMe2 & Ph3P

HCHO, MECHO, EtCHO, EtCOMe, PhCHO, PhCOMe, CH 3  N  C  O

PhCOPh, CH 2  C  O, CH 2  CH  CHO, Cyclohexanone, CH 3  N  O

Chemical properties of alkenes :

1. Hydrogenation reaction :
i. Catalytic or direct hydrogenation
ii. Indirect hydrogenation

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M. P. I. ALKENES XI & XII

iii. Hydroboration reduction reaction

iv. Birch reduction reaction
2. Electrophilic addition reaction :
i. Addition of HX
ii. Adition of HBr
iii. Adition of HBr in the presence of peroxides
iv. Addition of of Br2 in CCl4
v. Addition of X2 in water
vi. Addition of HOX
vii. Addition of Br2 in brine solution
viii. Addition of ICl
ix. Addition of Cl-N=O
x. Addition of IN3
xi. Addition of CH2N2
xii. Addition of CH2I2 using zinc
xiii. Reaction with NBS it is free radical substitution reaction at allylic
position
xiv. Reaction with chlorine at high temperature (5000C) it is free radical
substitution reaction at allylic position
3. Hydration of alkenes :
i. Hydration of alkenes using dilute acids.
ii. Hydration of alkenes by OMDM reaction.
iii. Hydration of alkenes by hydroboration oxidation reaction.
4. Dimerization of alkenes using conc. H2SO4 or conc. HF.
5. Alkylation of alkenes using conc. H2SO4 or conc. HF at 00C & a
hydrocarbon contains tertiary-H atom.
6. Addition of aldehyes of prins reaction using dil acid.
7. Oxidation of alkenes :

3. Questions : Answer the followings :

Co  CO 
1 CH 3  CH  CH 2  CO  H 2O  2
AsO. A.
 8

Co  CO 
 2 CH 3  CH  CH 2  CO  ROH 
AsO . A.
2
 8

Co  CO 
 3 Ph  CH  CH 2  CO  H 2 2
AsO. A.
8

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M. P. I. ALKENES XI & XII
Co  CO 
 4 Ph  CH  CH 2  CO  H 2O 
AsO. A.
 2 8

Co  CO 
 5 Ph  CH  CH 2  CO  MeOH 
AsO. A.
 2 8

Co  CO 
 6  CH  CH  CO  H 2 
As O. A.

2 8

Co  CO 
 7  CH  CH  CO  H 2O 
AsO. A.
 2 8

Co  CO 
8 CH  CH  CO  MeOH 
AsO . A.
 2 8

Co  CO 
 9  Me  C  CH  CO  H 2 
AsO. A.
 2 8

Co  CO 
10  Me  C  CH  CO  H 2O 
As O. A.
 2 8

Co  CO 
11 Me  C  CH  CO  MeOH 
AsO . A.
 2 8

Co  CO 
12  Ph  C  CH  CO  H 2 
AsO . A.
 2 8

Co  CO 
13 Ph  C  CH  CO  H 2O 
As O. A.
 2 8

Co  CO 
14  Ph  C  CH  CO  MeOH 
AsO . A.
 2 8

4. Question : Solve the following problems :

R H
C O O CHN
5 5 aq. alc. Na2SO3
(1) + Os A B
C R.T. Reflux
O O
R H

O O CHN
5 5 aq. alc. Na2SO3
(2) + Os A Reflux B
O O R.T.

O O
C5H5N at R.T. A K3[Fe(CN)6]
(3) + Os B
aq. alc. Na2SO3
O O

OsO4 as a catalyst :
H2O2
(4) CH2 CH CHO
OsO4

H2O2
(5) CH2 CH CH3
OsO4
CH3

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M. P. I. ALKENES XI & XII

H2O2
(6) OsO4

CH COOH H2O2
(7) OsO4
CH COOH

4. Write the product of the following reactions :

Peracid
(i)
1 eq.

Peracid
(ii)
1 eq.

(iii) CF3CO3H
1 eq.

MCPBA
(iv)
1 eq.

MCPBA
(v)
2 eq.

(vi) MCPBA
1 eq.

MCPBA
(vii)
H3O+

H2O2
(viii)

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M. P. I. ALKENES XI & XII

H2O2
(ix) AcOH

5. Write products of the following with (A) Bayer’s reagent (B) OsO4 in
pyridine/H2O (C) Peracid/H2O.

(i) (ii) (iii) (iv)

Me
(v) (vi) (vii) (viii) H D

O
Write product of with the following :
6.

 i  MeOH / H   ii  MeO  / MeOH  iii  NH3  iv  R  NH 2

 v  LAH  vi  AlCl3 / LAH  vii  EtSK  viii  RMgX
 ix  NaN3  x  H  / KCN  xi  Al  OR 3  xii  Pure HCN

7. Question : Write the product for the following reactions :

KMnO4/H+
(1) R CH C
Heat
Me
KMnO4/H+
(2) Et CH C
Heat
Me
H
KMnO4/H+
(3) Et CH C
Heat
H
Me
KMnO4/H+
(4) H CH C
Heat
Me
Me
KMnO4/H+
(5) Me CH C
Heat
Me

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M. P. I. ALKENES XI & XII

KMnO4/H+
(6) Heat

KMnO4/H+
(7) Heat

KMnO4/H+
(8) Heat

KMnO4/H+
(9) Heat

KMnO4/H+
(10) Heat

KMnO4/H+
(11) Heat

KMnO4/H+
(12) Heat

KMnO4/H+
(13) Heat

KMnO4/H+
(14) Heat

+
(15) Me C C CH2 CH2 CH CH Me KMnO4/H
6 Heat

8. Oxidation of active methyl & methylene groups :

SeO2 CHO
(1) Me CHO
CHO
O
SeO2
(2) Me C Me

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M. P. I. ALKENES XI & XII

O
SeO2
(3) Ph C Me

COOEt COOEt
SeO2
(4) O
COOEt COOEt

O
SeO2
(5) CH3 CH2 C CH3

SeO2
(6)
N CH3
SeO2
(7) Ph CH2 Ph
O
SeO2
(8)

Some other reactions of alkenes that you have to revise from previous
content :

1. Ozonolysis of alkens :
2. Oxymercuration demercuration of alkenes :
3. Hydroboration deboration :
4. Addition of carbenes :
5. Allylic halogenations :
6. Walcker process :

9. Question : Solve the following problems :

Base
(1) CH2 CH C N + Ph2C N OH

0
(2) CH2 CH C N + NH3 25 C

Ac
(3) CH2 CH C N + CH2 Base
Ac 400C

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M. P. I. ALKENES XI & XII

(4) CH2 CH C N + CH3SH Base

250C

O
(5) CH2 CH C N + CH3 C R Base
250C

Base
(6) CH2 CH C N + 0
OH OH OH 50 C

10. Question: Identify A to Z in the given problems.

B alc. KOH KOH K2Cr2O7/H+

A D E NBS F G H
C
Cr2O3/H+ +
KMnO4/H+ I2/OH-
I H3O J K
Heat L
H3O+
S.L. H3O+
M+N O Conc. H2SO4 P NaOH Q R
Heat Heat
HNO2 HNO3 T Sn/HCl U HNO2 V H3PO2
S
O

W O OH-
X Y (Pink colour)

Br2/H2O

11. Question: Identify A to Z in the given problems.

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M. P. I. ALKENES XI & XII

B Br2 alc. KOH CCl NaOH

C
D hv E F H O4 G H KMnO4
2 2

Zn-Hg Br2 Me2CHMgBr Br2

I Heat J K L M N
HCl hv hv

NaNH2 KMnO4/OH- CaO A

O P+R
Heat

I2 + OH-

MeCO3H HIO4
F S U + T LAH V

HCl Mg
W Y MeCl Z
Et2O
Na/ Et2O

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