Advices For Studying Organic Chemistry

A summary of addition reactions of alkenes with 1-methylcyclopentene as

the organic substrate. A bond designated means that the

stereochemistry of the group is unspecified. For brevity the structure of

only one enantiomer of the product is shown, even though racemic

mixtures would be produced in all instances in which the product is chiral.

Summary of Addition Reactions of Alkynes

H 2 /NiB 2 (P-2 catalyst)

Syn addition

Li/NH 3 (or RNH 2 )

Anti addition

H 2 /Pt

X 2 (one molar equiv.)

Anti addition

HX (one molar equiv.)

Anti addition

1. O 3 , 2. HOAc or
   
   
   1. KMnO 4 , OH−,
   
   
   
   

Hydrogenation

Halogenation

Oxidation

C

C

R

R

2. H 3 O+

CC

H

R

H

R

CC

R

H

H

R

CH 2 CH 2

H

R

R R*

CC

R

X

X

R

X (^2) RCX
2 CX 2 R
Addition
CCR of HX
R X
HX RCH 2 CX 2 R
CC
OH
HO
R
OO