KNH2 + KCI NH3 ČI -30 °C NH2 chloro is only moderately electron-withdrawing traditional SAr reactions require heat !

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 41AP: In light of your answer to Problem 30-40, explain why a mixture of products occurs in the following...
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In this reaction, why doesn't the NH2 group trigger an elimination instead of the substitution reaction seen in the picture

Why can't the -NH2 remove a proton, causing the C-H bond to collapse and form a triple bond (benzyne), and the Cl is removed as a leaving group?

KNH2
+ KCI
NH3
-30 °C
NH2
traditional SAr
reactions require
chloro is only
moderately
electron-withdrawing
heat !
Transcribed Image Text:KNH2 + KCI NH3 -30 °C NH2 traditional SAr reactions require chloro is only moderately electron-withdrawing heat !
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