Open Question
Thioesters can react with nucleophiles to yield substitution products. Write a mechanism for the reaction of S-methyl ethanethioate with dimethylamine.
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23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides
Hydrolysis of Thioesters
Multiple Choice
Draw the structures of products A and B in the following reaction sequence.
A
B
C
D
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Verified step by step guidance1
Identify the starting materials: The reaction begins with an alkyl iodide and sodium thioacetate (CH3C(O)SNa).
Understand the first reaction: The sodium thioacetate acts as a nucleophile, attacking the carbon atom bonded to the iodine in the alkyl iodide, resulting in the substitution of the iodine with the thioacetate group. This is an SN2 reaction.
Draw the structure of product A: Replace the iodine in the alkyl iodide with the thioacetate group, resulting in a thioester.
Understand the second reaction: The thioester is treated with hydroxide ions (OH-) in water, which leads to hydrolysis. The hydroxide ion attacks the carbonyl carbon, leading to the cleavage of the thioester bond.
Draw the structure of product B: The hydrolysis of the thioester results in the formation of a thiol and a carboxylate ion. The thiol is the organic product B.
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