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(20 pts) Alcohol A undergoes a remarkable acid-catalyzed conversion to B. Me Me Me HO Me I Me S Me Me + HA H H (cat.) Me Me Me Me A Hmm Hmm Me Me 11111 Me B Me Me a. Provide a mechanism. It may take a while to draw out all the intermediates, but consider this as a step- by-step process, although one could also imagine mechanistic alternatives where all or some of the steps are concerted. (attach additional page with your mechanism) b. What do you notice about the stereochemistry of each 1,2-shift in your mechanism (or at least where the stereochemistry of the shift is apparent from the structure of B)? c. How many 1,2-shifts are there in total? d. Give a one-word name to the final step in your mechanism.

(20 pts) Alcohol A undergoes a remarkable acid-catalyzed conversion to B. Me Me Me HO Me I Me S Me Me + HA H H (cat.) Me Me Me Me A Hmm Hmm Me Me 11111 Me B Me Me a. Provide a mechanism. It may take a while to draw out all the intermediates, but consider this as a step- by-step process, although one could also imagine mechanistic alternatives where all or some of the steps are concerted. (attach additional page with your mechanism) b. What do you notice about the stereochemistry of each 1,2-shift in your mechanism (or at least where the stereochemistry of the shift is apparent from the structure of B)? c. How many 1,2-shifts are there in total? d. Give a one-word name to the final step in your mechanism.

Organic Chemistry
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
Chapter24: Catalytic Carbon-carbon Bond Formation
Section: Chapter Questions
Problem 24.36P
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(20 pts) Alcohol A undergoes a remarkable acid-catalyzed conversion to B. Me Me Me HO Me I Me S Me Me + HA H H (cat.) Me Me Me Me A Hmm Hmm Me Me 11111 Me B Me Me a. Provide a mechanism. It may take a while to draw out all the intermediates, but consider this as a step- by-step process, although one could also imagine mechanistic alternatives where all or some of the steps are concerted. (attach additional page with your mechanism) b. What do you notice about the stereochemistry of each 1,2-shift in your mechanism (or at least where the stereochemistry of the shift is apparent from the structure of B)? c. How many 1,2-shifts are there in total? d. Give a one-word name to the final step in your mechanism.
Transcribed Image Text:(20 pts) Alcohol A undergoes a remarkable acid-catalyzed conversion to B. Me Me Me HO Me I Me S Me Me + HA H H (cat.) Me Me Me Me A Hmm Hmm Me Me 11111 Me B Me Me a. Provide a mechanism. It may take a while to draw out all the intermediates, but consider this as a step- by-step process, although one could also imagine mechanistic alternatives where all or some of the steps are concerted. (attach additional page with your mechanism) b. What do you notice about the stereochemistry of each 1,2-shift in your mechanism (or at least where the stereochemistry of the shift is apparent from the structure of B)? c. How many 1,2-shifts are there in total? d. Give a one-word name to the final step in your mechanism.
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