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Question

Absolute configuration of the chiral centres (C-2, C-4) and prochirality descriptors (HA and HB) in the following compound is :

The correct answer is

2R, 4S; HA : Pro-s; HB : Pro-r

The stem carries a drawn structure; the four options are text and are reproduced in full above.

The question combines two related assignments.

Absolute configuration at C-2 and C-4 follows the ordinary CIP procedure: rank the four groups at each centre, orient the lowest away, and read the sense of 1→2→3. At a carbon bearing OH, COOH, CH2 and H, the ranking is OH > COOH > CH2 > H, since oxygen beats carbon directly, and the carboxyl carbon (O,O,O by duplication) beats a methylene carbon.

Prochirality at C-3 is the more interesting half. The two hydrogens HA and HB sit on the same carbon and look equivalent, but they are diastereotopic here because the molecule already contains stereocentres. The test is a thought experiment: replace one hydrogen with a group of higher priority (conventionally deuterium) and assign the resulting centre. If replacing it gives R, that hydrogen is pro-R; if S, it is pro-S. Then do the same for the other hydrogen.

Because the two hydrogens must give opposite answers, one is always pro-R and the other pro-S — which is why every option pairs them that way and the real work is deciding which is which.

This distinction is not merely formal. Enzymes routinely discriminate between the pro-R and pro-S hydrogens of a CH2 group, removing one and leaving the other untouched, and it was exactly this kind of stereospecific labelling that established the mechanisms of reactions in the citric acid cycle — the classic case being aconitase, which distinguishes the two apparently identical CH2COOH arms of citrate.

Per the official final answer key the answer is option (A), 2R, 4S with HA pro-s and HB pro-r.

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