ELECTROSTATIC POTENTIAL MAPS OF CARBANIONS

Derived computationally provide an indication of charge localization RED = NEGATIVE

BLUE = POSITIVE
H

SUMMARY OF ALKYNE CHEMISTRY

R
R

Br

Br

Br

HBr

E+
R

Na

Br2

NaNH2

R
Br

BH3
R

Br

BrBr

Br

HO

BH 2

H
OH
Tautomerization

slow

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

H 2O2 /NaOH

Br2

Br

Reaction of internal alkynes:

O
Hydrogenation

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

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

Tautomerization

REACTION OF ACETYLIDE ANIONS

WITH ELECTROPHILES

OH

H2O

Na

Ketones

or ROH or RCO2H

R-X

O
R

Primary or
will get
elimination

Aldehydes

epoxides R

OH
OH

H
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

NaNH2

Br

H2

poisoned catalyst

Pd/C Quinoline