(a) Provide a curved arrow mechanism for the reaction shown below, commenting on the stereochemical outcome. Aco Aco AcO- AcO- OAC PhSH, BF3 OEt2 CH₂Cl₂ ACO ACO ACO ACO Ho ŠPh Major product (b) Which spectroscopic technique would you use to determine the stereochemistry at the anomeric centre of a sugar? Describe what

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter5: Stereochemistry At Tetrahedral Centers
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Problem 60AP: The first step in the metabolism of glycerol, formed by digestion of fats, is phosphorylation of the...
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4.
(a) Provide a curved arrow mechanism for the reaction shown below,
commenting on the stereochemical outcome.
Aco Aco
AcO-
ACO
OAC
PhSH, BF3 OEt2
CH₂Cl2
Aco Aco
AcO-
ACO
SPh
Major product
(b) Which spectroscopic technique would you use to determine the
stereochemistry at the anomeric centre of a sugar? Describe what
you would expect to see for a-D-glucopyranose and why.
Transcribed Image Text:4. (a) Provide a curved arrow mechanism for the reaction shown below, commenting on the stereochemical outcome. Aco Aco AcO- ACO OAC PhSH, BF3 OEt2 CH₂Cl2 Aco Aco AcO- ACO SPh Major product (b) Which spectroscopic technique would you use to determine the stereochemistry at the anomeric centre of a sugar? Describe what you would expect to see for a-D-glucopyranose and why.
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