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ALKENES
(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
1
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
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
1. Hydrogenation reaction :
i. Catalytic or direct hydrogenation
ii. Indirect hydrogenation
2
M. P. I. ALKENES XI & XII
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
3
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
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
4
M. P. I. ALKENES XI & XII
H2O2
(6) OsO4
CH COOH H2O2
(7) OsO4
CH COOH
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)
5
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.
Me
(v) (vi) (vii) (viii) H D
O
Write product of with the following :
6.
6
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
7
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 :
0
(2) CH2 CH C N + NH3 25 C
Ac
(3) CH2 CH C N + CH2 Base
Ac 400C
8
M. P. I. ALKENES XI & XII
O
(5) CH2 CH C N + CH3 C R Base
250C
Base
(6) CH2 CH C N + 0
OH OH OH 50 C
W O OH-
X Y (Pink colour)
Br2/H2O
9
M. P. I. ALKENES XI & XII
I2 + OH-
MeCO3H HIO4
F S U + T LAH V
HCl Mg
W Y MeCl Z
Et2O
Na/ Et2O
10