Malic acid, C4 H6 O5, has been isolated from apples. Because...

Malic acid, $\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}_{5}$, has been isolated from apples. Because this compound reacts with 2 molar equivalents of base, it is a dicarboxylic acid. (a) Draw at least five possible structures. (b) If malic acid is a secondary alcohol, what is its structure?

Malic acid, $\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}_{5}$, has been isolated from apples. Because this compound reacts with 2 molar equivalents of base, it is a dicarboxylic acid.
(a) Draw at least five possible structures.
(b) If malic acid is a secondary alcohol, what is its structure?

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Key Concepts

Dicarboxylic Acids

Dicarboxylic acids are organic compounds containing two carboxyl (–COOH) groups. Each carboxyl group can donate a proton, which is why such acids typically react with two equivalents of a base. This characteristic reactivity is central to their behavior in acid-base reactions and influences their chemical properties and potential biological roles.

Structural Isomerism

Structural isomerism refers to the phenomenon where molecules with the same molecular formula have different connectivity among their atoms. In the context of malic acid, multiple distinct structures (or isomers) can be drawn by rearranging the positions of the carboxyl and hydroxyl groups, illustrating how atoms can be connected in several ways while still conforming to C4H6O5.

Secondary Alcohol

A secondary alcohol is characterized by a hydroxyl group (–OH) attached to a secondary carbon, which is a carbon bonded to two other carbon atoms. Identifying malic acid as a secondary alcohol in one of its isomers means that the hydroxyl group is not at the end of the carbon chain but rather on an internal carbon, affecting both its reactivity and physical properties.

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