PROBLEM 12.46
Question
Question: a) What product is formed in Step [1] of the following reaction sequence?
(b) Draw a mechanism for Step [2] that accounts for the observed stereochemistry.
(c) What reaction conditions are necessary to form chiral A from prop-2-en-1-ol
Step-by-Step Solution
Verified Answer
Answer
a.
b.
c.
1Reaction of alcohols with methane sulfonyl chloride
The reaction of alcohols with methane sulfonyl chloride yields the corresponding methane sulfonates by the replacement of the hydrogen atom of the OH group by SO2CH3 .
2Product obtained in step [1]
The reaction of the given compound with CH3SO2Cl is shown below:
Reaction of A with CH3SO2Cl
3Mechanism of step [2]
The mechanism of the given reaction is provided below.
Mechanism
4Preparation of chiral A using prop-2-en-1-ol
The preparation of chiral A from prop-2-en-1-ol can be carried out as shown below.
Synthesis of A
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