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 16.49P: (R)-Pulegone, readily available from pennyroyal oil, is an important enantiopure building block for...
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Question
![Practice Problem 13.38d
Propose a plausible mechanism for the following transformation.
OH
[H,SO4]
MeSH
Mes](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F776b81b2-5984-443d-93b2-d351507602c0%2F0145e517-81e5-40cd-bb93-d41d1f9160aa%2Fyoccar2_processed.png&w=3840&q=75)
Transcribed Image Text:Practice Problem 13.38d
Propose a plausible mechanism for the following transformation.
OH
[H,SO4]
MeSH
Mes
![13.38d1
O Get help answering Molecular Drawing questions.
Add curved arrow(s) to draw step 1 of the mechanism. Modify the given drawing of the product as needed to show the intermediate that is formed in this step.
to
H,C-
+ H-OH,
Н— он,
Edit
H;C](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F776b81b2-5984-443d-93b2-d351507602c0%2F0145e517-81e5-40cd-bb93-d41d1f9160aa%2F6ejo54v_processed.png&w=3840&q=75)
Transcribed Image Text:13.38d1
O Get help answering Molecular Drawing questions.
Add curved arrow(s) to draw step 1 of the mechanism. Modify the given drawing of the product as needed to show the intermediate that is formed in this step.
to
H,C-
+ H-OH,
Н— он,
Edit
H;C
Expert Solution
![](/static/compass_v2/shared-icons/check-mark.png)
Step 1
Sequence in the mechanism :-
- Protonation of etheral oxygen
- Attack of nucleophile to the most substituted site
- Deprotonation to form product
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