[image]

Markovnikov addition

1,2-methyl shift

[image]

Markovnikov addition

1,2-hydride shift

[image]

Bromonium ion intermediate

Anti addition (stereospecific) 

[image]

Markovnikov addition

Bromonium ion intermediate

Anti addition (stereospecific) 

[image]

Carbocation intermediate

1,2-hydride shift

[image]

Carbocation intermediate

1,2-hydride shift

[image]

Markovnikov addition

Cyclic mercurinium ion intermediate

Organomercury intermediate

[image]

Anti-markovnikov addition

Syn addition

T.S.1: 4 membered ring

Organiborane intermediate 

[image]

Anti-markovnikov addition

Syn addition

T.S.1: 4 membered ring

organiborane intermediate 

[image]

Syn addition

(stereospecific)

[image]

Trans epoxide

(stereospecific)

[image]

Z Isomer 

[image]

Trans dihalide

[image]

Tautomerisation of enol

[image]

Markovnikov addition

T.S. 1: mercurinium ion

Mercuric enol intermediate  

Tautomerisation of enol to release Hg²⁺ 

and form a ketone

[image]

Anti-markovnikov addition

Organoborane intermediate 

Oxidation of organoborane intermediate to form enol

Tautomerisation of enol

[image]

Complete reduction of alkyne to alkane

[image]

Syn addition 

Cis alkene as product

[image]

Trans alkene as product 

[image]

Formation of acetylide ion (a good nucleophile) 

Formation of C-C bond 

Terminal alkyne coverted to a longer internal alkyne