Using the information below explain why CN- is a stronger Bronsted base even though in the reaction given it is only 300 fold more nucleopihlic.

Pushing Electrons
4th Edition
ISBN:9781133951889
Author:Weeks, Daniel P.
Publisher:Weeks, Daniel P.
Chapter3: Mechanisms
Section: Chapter Questions
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Using the information below explain why CN- is a stronger Bronsted base even though in the reaction given it is only 300 fold more nucleopihlic. 

 

pKa of conjugate acid
k (second order rate constant
for the reaction shown below)
M1. s1
Nucleophile name
Br
-8
1.3
CN-
9.4
3.2 X 102
Nuc: + CH3I
Nuc-CH3 + I
DMF
25 °C
Transcribed Image Text:pKa of conjugate acid k (second order rate constant for the reaction shown below) M1. s1 Nucleophile name Br -8 1.3 CN- 9.4 3.2 X 102 Nuc: + CH3I Nuc-CH3 + I DMF 25 °C
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