Q35P - Organic Chemistry (Mcmurry)

Question

Isocitric acid, an intermediate in the citric acid cycle of food metabolism, has the systematic name (2R,3S)-3-carboxy-2-hydroxypentane-dioic acid. Draw the structure.

Step-by-Step Solution

Answer

The structure of isocitric acid which has the systematic name (2R,3S)-3-carboxy-2-hydroxypentane-dioic acid is

Step 1: Definition of structure

The arrangement of chemical bonds between atoms in a molecule is defined as the structure.

Step 2: Explanations

The name of isocitric acid shows that it has a five-carbon straight chain with three carboxyl groups, one at $C_1$  other attached to $C_3$ , a third one at  $C_5$ and a hydroxyl group on  $C_2$.

When viewed from the group of lowest priority, the groups with first, second, and third-highest priorities are arranged in a clockwise direction on  $C_2$ an in an anticlockwise direction on $C_3$.

The structure of isocitric acid which has the systematic name (2R, 3S)-3-carboxy-2-hydroxypentane-dioic acid is