3. Give an explanation for the following experimental observations and accurate reaction mechanisms for each transformation: (a) exposure of 3 to a catalytic amount of NaOEt results in no reaction, but treatment of 4 under the same conditions causes isomerization to 5. 3 Me H cat. NaOEt no rx. Me H 4 cat. NaOEt Me H 5

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
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.37P: Following are the steps in the industrial synthesis of glycerin. Provide structures for all...
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3.
Give an explanation for the following experimental observations and write
accurate reaction mechanisms for each transformation:
(a) exposure of 3 to a catalytic amount of NaOEt results in no reaction, but
treatment of 4 under the same conditions causes isomerization to 5.
3
Me
H
cat.
NaOEt
no rx.
cat.
$=0
NaOEt
Me
Me
H
5
Transcribed Image Text:3. Give an explanation for the following experimental observations and write accurate reaction mechanisms for each transformation: (a) exposure of 3 to a catalytic amount of NaOEt results in no reaction, but treatment of 4 under the same conditions causes isomerization to 5. 3 Me H cat. NaOEt no rx. cat. $=0 NaOEt Me Me H 5
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