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Under mild acidic conditions, 5-Hydroxypentanoic acid cyclizes to give which of the following compounds?

a. 4-Hydroxytetrahydrofuran
b. 4-Hydroxy-2-pentanone
c. 2-Hydroxy-5-pentanone
d. 2-Hydroxy-2-pentenoic acid

User Insula
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Final answer:

Under mild acidic conditions, 5-Hydroxypentanoic acid cyclizes to form 4-Hydroxytetrahydrofuran, as the intramolecular attack of the hydroxy group on the carboxylic acid group forms a five-membered lactone ring.

Step-by-step explanation:

Under mild acidic conditions, 5-Hydroxypentanoic acid cyclizes to form a cyclic ester, which is more commonly referred to as a lactone. The cyclization would involve the formation of a five-membered ring as the hydroxy group (OH) from the 5th carbon atom attacks the carbonyl carbon of the carboxylic acid (COOH). This intramolecular esterification yields a compound known as 4-Hydroxytetrahydrofuran.

The correct answer to the question is option a. 4-Hydroxytetrahydrofuran. This is because when a five-carbon acid like 5-Hydroxypentanoic acid cyclizes, it forms a four-membered ring with one oxygen (resulting from the -OH group and the carbonyl group) and this structure matches that of tetrahydrofuran with a hydroxy group at the 4-position.

User Aquaraga
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