UPSC Civil Services (Mains), Chemistry optional · 2023 · Paper II
Q1(b)(i). IUPAC name with stereodescriptors
Question
Write the IUPAC nomenclature of the above compound by assigning the stereochemistry. [structure given in the paper]
Answer in brief
(2R,3R)-3-Chloro-2-hydroxypent-4-enal.
Key points
- Parent: pentanal, CHO = C-1; C=C is 4-ene; chloro before hydroxy.
- CIP order: C-2: OH > C-3 > CHO > H; C-3: Cl > C-2 > C-4 > H.
- Lowest priority H faces the viewer: anticlockwise is reversed, giving R.
The full model answer
As written for the answer booklet: the diagram carries the working, the lines stay short. Read here only; it is not offered as a download.

CoversIUPAC nomenclatureR/S configurationCIP sequence rulesstereodescriptors3-chloro-2-hydroxypent-4-enal
All parts of Question 1
- 1(a)(i) Acidity of cyclopentadiene5 marks
- 1(a)(ii) Hydrogen exchange in cyclopropyl and cyclopropenyl ketones5 marks
- 1(b)(i) IUPAC name with stereodescriptors5 marks
- 1(b)(ii) Dimerisation ability of three triarylmethyl-type radicals5 marks
- 1(c) Methyl iodide with sodium azide: DMF against methanol10 marks
- 1(d) Photochemical electrocyclic closure of two cyclonona-1,3-dienes10 marks
- 1(e)(i) 2-Chloro-6-methylcyclohexanone with methoxide5 marks
- 1(e)(ii) Name reaction that gives nitrogen as a by-product5 marks