What is stereo structural IUPAC name of the following compound?

pub chem

1 Answer
Feb 28, 2017

The name of the compound is (2S,3R)-2-bromo-3-chloropropane.

Explanation:

Configuration at "C-2"

C2

The Cahn-Ingold-Prelog priorities of the groups on "C-2" are

"Br = 1; C-3 = 2; C-1 = 3; H = 4"

The "H" atom is furthest from our eye, and the 1 → 2 → 3 direction is counterclockwise.

Thus, the configuration at "C-2" is S.

Configuration at "C-3"

C3

The Cahn-Ingold-Prelog priorities of the groups on "C-3" are

"Cl = 1; C-2 = 2; C-4 = 3; H = 4"

The "H" atom is closest to our eye, and the 1 → 2 → 3 direction is counterclockwise.

The configuration at "C-3" appears to be S.

However, because the "H" atom is closest to our eye, we invert the assignment.

The configuration at "C-3" is R.

The name of the compound is, therefore, (2S,3R)-2-bromo-3-chlorobutane.

NOTE:

Your image was the PubChem structure for (2S,3S)-2-bromo-3-chloro-butane.

They give three structures.

Wedge-Dash

Wedge-Dash
(From PubChem)

This is the (2S,3S) isomer.

Wire Frame

This is the structure you give.

Amazingly, PubChem is incorrect. This is the (2S,3R) isomer.

3-Dimensional

3D
(From PubChem)

This is the correct (2S,3S) structure.