Why does this synthesis fail? OH 1. CH3Mgl, ether 2. H₂O, H* OH ОН The organic starting material is insoluble in ether.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.26P: Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and...
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Why does this synthesis fail?

Why does this synthesis fail?
A.
OH
B.
C.
D.
1. CH3Mgl, ether
2. H₂O, H*
OH
OH
The organic starting material is insoluble in ether,
The organic starting material contains a hydrogen which is acidic enough to react with a
Grignard reagent.
The carbonyl group is too hindered to be readily attacked by the Grignard reagent.
Magnesium is insoluble in ether.
Transcribed Image Text:Why does this synthesis fail? A. OH B. C. D. 1. CH3Mgl, ether 2. H₂O, H* OH OH The organic starting material is insoluble in ether, The organic starting material contains a hydrogen which is acidic enough to react with a Grignard reagent. The carbonyl group is too hindered to be readily attacked by the Grignard reagent. Magnesium is insoluble in ether.
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