ELECTROSTATIC POTENTIAL MAPS OF CARBANIONS

Derived computationally provide an indication of charge localization -

RED = NEGATIVE BLUE = POSITIVE
H H

H H
H
H

H
 SUMMARY OF ALKYNE CHEMISTRY

R R
R
R E
Br Br
Br

E+ HBr

Br2 R Br Br2 R Br
R Na R
NaNH2 Br slow BrBr Br

BH3 H 2O/H+/Hg2+ catalyst if terminal

R H
R R R
H BH 2
H 2O2 /NaOH HO O
Tautomerization
R H

H OH
Tautomerization

R H
Reaction of internal alkynes:

Hydrogenation
O
SYN addition of H2 - H2 /Pd/C, quinoline poison to afford Z alkene

ANTI addition of H2 - Na/NH3 to afford E alkene

 REACTION OF ACETYLIDE ANIONS

WITH ELECTROPHILES

OH

R
R H2O
Na H
R Ketones or ROH or RCO2H
R

O R-X
Primary or R
R H will get
elimination
Aldehydes O

epoxides R
+
E
OH

H OH

R R

E
 RETROSYNTHETIC ANALYSIS

A process of reasoning backwards from a target molecule to a suitable set of starting

materials

Br

Br
 SYNTHESIS

NaNH2 Br
H H
H H

H NaNH2 Br

H2

poisoned catalyst
H H

Pd/C Quinoline