Answered: H. :0: *0-H он :0 :0: H-OSO,H H,ö: HSO4…

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H. :0: *0-H он :0 :0: H-OSO,H H,ö: HSO4 A B D E acetal hemiacetal + HSO4 + CH;OH + H,SO4

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 59AP

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Question

Four of the seven steps in the mechanism for this process are shown in the conversion of acetal A to hemiacetal E.

a.) Add curved arrows for each step

b.) Draw another resonance structure for C.
c.) Identify the nucleophile and electrophile in Step [3].
d.) Which steps are Brønsted–Lowry acid–base reactions?

H.
:0: *0-H
он
:0
:0:
H-OSO,H
H,ö:
HSO4
A
B
D
E
acetal
hemiacetal
+ HSO4
+ CH;OH
+ H,SO4

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