49E - Organic Chemistry (Mcmurry)

Question

Malic acid, ${\mathbf{C}}_4{\mathbf{H}}_6{\mathbf{O}}_5$, has been isolated from apples. Because this compound reacts with 2 molar equivalents of base, it is a dicarboxylic acid .

a) Draw at least 5 possible structures

b) If malic acid is secondary alcohol what is its structure?

Step-by-Step Solution

Answer

a) The 5 structures of malic acid correspond to, diglycolic acid,2-hydroxy-2-methyl propane dioic acid, L-Malic acid, D-Malic acid and dimethyl-dicarbonate

b) The structure will then correspond to 2-hydroxy butane dioic acid.

Step 1: Malic acid

Malic acid is a substance that is obtained from fruits and wines. The molecular formula${\mathbf{C}}_4{\mathbf{H}}_6{\mathbf{O}}_5$ is and its chemical name is 2-hydroxy butane dioic acid.it is used as a medicine. People use it in treatment of fibromyalgia, for tiredness. In food, malic acid is used as a flavouring agent while in manufacturing it is used to balance the acidity of cosmetics.

Step 2:Structures possible

Step 3: Structures if malic acid is secondary alcohol