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Which of the following terms accurately describes the new functional group that results from the cyclization of the straight chain form of fructose?

Question

Which of the following terms accurately describes the new functional group that results from the cyclization of the straight chain form of fructose?

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Solution

The cyclization of the straight chain form of fructose results in a functional group known as a hemiketal.

Here's the step-by-step process:

  1. Fructose, in its straight-chain form, is a ketohexose, meaning it's a six-carbon sugar with a ketone functional group.

  2. During cyclization, the ketone group at the second position (C2) reacts with the hydroxyl group at the fifth position (C5).

  3. This reaction forms a five-membered ring structure, specifically a furanose ring (because it resembles the structure of furan, a five-membered aromatic ring).

  4. The functional group that results from this reaction is a hemiketal, which consists of a carbon atom bonded to an alkyl group, two oxygen atoms (one through a single bond and one through a double bond), and a hydrogen atom.

So, the term that accurately describes the new functional group that results from the cyclization of the straight chain form of fructose is a hemiketal.

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