What is the product of the following reaction? Hint: Be sure to consider a keto-enol tautomerization of an intermediate! H3C-CC-H O CH3C(OH)=CH₂ O CH₂CH=CHOH (cis) O CH3CH2CHO O (CH3)2C=O OCH₂CH=CHOH (trans) 1. HgSO4, H₂SO4 H₂O 2. H*

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
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What is the product of the following reaction? Hint: Be sure to
consider a keto-enol tautomerization of an intermediate!
H3C C C-H
O CH3C(OH)=CH₂
O CH₂CH=CHOH (cis)
O CH3CH2CHO
O (CH3)2C=O
O CH₂CH=CHOH (trans)
1. HgSO4, H₂SO4
H₂O
2. H*
Transcribed Image Text:What is the product of the following reaction? Hint: Be sure to consider a keto-enol tautomerization of an intermediate! H3C C C-H O CH3C(OH)=CH₂ O CH₂CH=CHOH (cis) O CH3CH2CHO O (CH3)2C=O O CH₂CH=CHOH (trans) 1. HgSO4, H₂SO4 H₂O 2. H*
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