-Draw the transition state showing the allowed homo and lumo interaction of the mechanism   -Draw the transition state showing the forbidden Homo/Lumo interaction for the mechanism

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
Problem 28MP
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-Draw the transition state showing the allowed homo and lumo interaction of the mechanism  

-Draw the transition state showing the forbidden Homo/Lumo interaction for the mechanism 

a) Mechanism-
Na CN
+ H3C-Br
NC-CH3
Na Br
bromomethane
acetonitrile
H
H
EC
Н— с
Br
N
c-----Br
H
H
Back side attack
Transition state
NE
CH3
One step concerted mechanism.
• Bond breaking and making takes place simultaneously.
Transcribed Image Text:a) Mechanism- Na CN + H3C-Br NC-CH3 Na Br bromomethane acetonitrile H H EC Н— с Br N c-----Br H H Back side attack Transition state NE CH3 One step concerted mechanism. • Bond breaking and making takes place simultaneously.
• HOMO = Highest occupied molecular orbital.
• LUMO = Lowest unoccupied molecular orbital
• HOMO-LUMO interaction between nucleophile and substrate leads to formation of bond.
• HOMO of nucleophile and LUMO of alkyl halide.
• Non-bonding orbital or lone pair of CN is HOMO.
• Anti-bonding orbital of bromomethane is LUMO.
%3D
NC -CH3
CN
+
H3C-Br
n
Oco O Br C
HOMO
LUMO
Transcribed Image Text:• HOMO = Highest occupied molecular orbital. • LUMO = Lowest unoccupied molecular orbital • HOMO-LUMO interaction between nucleophile and substrate leads to formation of bond. • HOMO of nucleophile and LUMO of alkyl halide. • Non-bonding orbital or lone pair of CN is HOMO. • Anti-bonding orbital of bromomethane is LUMO. %3D NC -CH3 CN + H3C-Br n Oco O Br C HOMO LUMO
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