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Assign the chiral descriptors for the following molecule :

Dimethyl ester with carbons numbered 1 to 5: an amino group on C3, a hashed ester bond on C2 whose carbonyl oxygen is labelled 18O, and a C4=C5 double bond carrying a vinyl and a phenyl group

  • A.2S, 3S, E
  • B.2R, 3S, Z
  • C.2S, 3R, E
  • D.2S, 3R, Z

Answer: C

The descriptors are 2S, 3R, E, option C.

C-2: the two ester carbons both rank above C-3 (O,O,O against N,C,H). They are tied until the isotope is reached, and the carbon carrying 18O outranks the one with 16O, so the order is C(18O ester) > C-1 > C-3 > H. With H towards the viewer the turn is reversed, giving S.

C-3: N is first. C-2 and C-4 are both (C,C,H), so go one sphere further: C-2 holds two ester carbons (O,O,O) while C-4 holds C-5 (C,C,C) and a duplicate carbon, so C-2 outranks C-4. The order is N > C-2 > C-4 > H, and with H pointing away N to C-2 to C-4 runs clockwise, so 3R.

C-4=C-5: on C-5 phenyl (C,C,C) outranks vinyl (C,C,H), and on C-4 C-3 outranks H. They sit on opposite sides, so E.

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