Organic Chemistry: Concepts and Applications - Headley Allan D. 2020

Heteroatomic Functional Groups and Organic Nomenclature
3.11 Structure and Properties of Anhydrides

Anhydrides are compounds that typically have a strong odor, they are also lachrymators, corrosive to the eyes, can cause blisters, and they are very reactive with water. Owing to the reactivity of these compounds, they are typically used as intermediates for the synthesis of other compounds. Commonly used anhydrides are shown below. Note that they are symmetrical around a central oxygen atom and the two carbonyl groups; this feature is typical for most common anhydrides, but there are others where this is not the case.

3.11.1 Nomenclature of Anhydrides

The root nomenclature of anhydrides is alkanoic alkonoic anhydride of which the carbonyl carbon is a part of the chain included in the alkanoic group, as demonstrated below.

Based on this system, the name for the anhydride shown below is ethanoic propanoic anhydride. Since “E” comes before “P” in the alphabet, the ethanoic portion comes first in the nomenclature of this molecule.

Problem 3.19

i. Give the IUPAC names for the molecules shown below.

ii. Give line-angle structures for the molecules shown below.

1. Butanoic ethanoic anhydride

2. 3-Choropentanoic propanoic anhydride

3. Cyclopentylmethanoic pentanoic anhydride