Concept Summary

Amides, Esters, and Anhydrides

Reactivity Principles

Amides  are the condensation    products    of  carboxylic  acids   and ammonia or  amines.

Amides  are given   the suffix  –amide. The alkyl   groups  on  a   substituted amide   are written at  the

beginning   of  the name    with    the prefix  N–.

Cyclic  amides  are called  lactams.    Lactams are named   by  the Greek   letter  of  the carbon

forming the bond    with    the nitrogen    (β-lactam,  γ-lactam,   and so  on).

Esters  are the condensation    products    of  carboxylic  acids   with    alcohols    (Fischer    esterification).

Esters  are given   the suffix  –oate.  The esterifying group   is  written as  a   substituent,    without a

number.

Cyclic  esters  are called  lactones.   Lactones    are named   by  the number  of  carbons in  the ring    and

the Greek   letter  of  the carbon  forming the bond    with    the oxygen  (α-acetolactone,    β-

propiolactone,  and so  on).

Triacylglycerols,   which   are a   form    of  fat storage,    include three   ester   bonds   between glycerol

and fatty   acids.  Saponification  is  the breakdown   of  fat using   a   strong  base    to  form    soap    (salts

of  long-chain  carboxylic  acids).

Anhydrides  are the condensation    dimers  of  carboxylic  acids.

Symmetric   anhydrides  are named   for the parent  carboxylic  acid,   followed    by  anhydride.

Asymmetric  anhydrides  are named   by  listing the parent  carboxylic  acids   alphabetically,

followed    by  anhydride.

Some    cyclic  anhydrides  can be  synthesized by  heating dioic   acids.  Five-   or  six-membered    rings

are generally   stable.