Q.5-5-59E

Question

The dehydration of citrate to yield cis-aconitate, a step in the citric acid cycle, involves the pro-R “arm” of citrate rather than the pro-S arm. Which of the following two products is formed?

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Answer

The product formed by dehydration of citrate is shown below.

1Dehydration

Dehydration is the chemical reaction involving water removal. In the dehydration of citrate, water removal occurs and results in forming cis-aconitate. The products are formed by keeping the prochirality in mind.

2The product formed in the reaction

We can assign pro R and pro S prochirality by the replacement test. So, the right “arm” of citrate is pro-R, and the product is formed, keeping the pro-S arm unchanged. The OH and H groups leave the molecule from the opposite sides. Thus, the product placed on the right is formed and is shown below.

The product formed by dehydration of citrate

Q5-5-47E

Q. 5-5-60E

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