O=C=0 Equation 1 H3C OCH3 CH3OH H Equation 2 O=C=0 Ph CH3OH H₂O 0=0 H3COH C OCH3 Ph. OH

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter7: Cycloalkanes
Section: Chapter Questions
Problem 3E: Which pair has more in common with one another?
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Question

Ketenes are highly reactive carbonyl compounds that easily hydrolyze to give carboxylic acids, or
solvolyze (e.g., with methanol) to give methyl esters (Equation 1). Consider the methanolysis of the
substituted ketene shown below (Equation 2). The methyl ester is formed as expected, but the epoxide
undergoes a rearrangement to give the unsaturated alcohol product.

Draw the structures for each step of this process (use the pushing electron method to show how each step occurs). include lone pairs 

- start with the methanol oxygen lone pair attacking the carbonyl
carbon of the ketene.

O=C=0
Equation 1
H3C OCH3
CH3OH
H
Equation 2
O=C=0
Ph
CH3OH
H₂O
0=0
H3COH
C
OCH3
Ph.
OH
Transcribed Image Text:O=C=0 Equation 1 H3C OCH3 CH3OH H Equation 2 O=C=0 Ph CH3OH H₂O 0=0 H3COH C OCH3 Ph. OH
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