This reaction cannot go to completion as drawn. Why? H2N + CI HN- A) The amine will act as a Lewis base B) The HCI that forms will protonate the amine and stop the reaction halfway C) The pKa of the amine is too low D) The pKa of the conjugate acid of the amine is too low

Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
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This reaction cannot go to completion as
drawn. Why?
H2N
HN-
A) The amine will act as a Lewis base
B) The HCl that forms will protonate the
amine and stop the reaction halfway
C) The pKa of the amine is too low
D) The pka of the conjugate acid of the
amine is too low
Transcribed Image Text:This reaction cannot go to completion as drawn. Why? H2N HN- A) The amine will act as a Lewis base B) The HCl that forms will protonate the amine and stop the reaction halfway C) The pKa of the amine is too low D) The pka of the conjugate acid of the amine is too low
Expert Solution
Step 1

This amide synthesis reaction:

They are commonly synthesised by the reaction of acid chlorides with an amine, the two step sequence which begins with reacting an amine (or ammonia) with an acid chloride and follows with reduction of the amide using lithium aluminum hydride results in the substitution of an alkyl group on the nitrogen. Here only first step is shown which is not a complete set of reaction as it will not go to completion without the 2nd step being followed.

 

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