H. н Н. N. O-PP one step но он но Он но ОН UMP HO-PP エー O: Zーエ

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter4: Polar Bonds, Polar Reactions
Section: Chapter Questions
Problem 8CTQ
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Uridine monophosphate (UMP) is one of the four nucleotides that compose RNA, the nucleic acid that translates the genetic information of DNA into proteins needed by cells for proper function and development. A key step in the synthesis of UMP is the SN1 reaction of A with B to form C, which is then converted to UMP in one step. Draw a stepwise mechanism for this SN1 reaction.

H.
н
Н.
N.
O-PP
one step
но
он
но
Он
но
ОН
UMP
HO-PP
エー
O:
Zーエ
Transcribed Image Text:H. н Н. N. O-PP one step но он но Он но ОН UMP HO-PP エー O: Zーエ
Expert Solution
Step 1

The step wise mechanism is as follows,

The reaction between compound A and compound proceeds through SN1 mechanism which means that generation of carbocation takes place in the reaction.

The first step involves the abstraction of proton from nitrogen atom of N-H bond by oxygen atom of –O– PP bond. This brings positive charge on oxygen atom and negative charge on nitrogen atom as shown below,

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