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Naming and Properties of Esters

  • An ester group is made up of a carbonyl group (C=O) bonded to an oxygen atom
Properties:
  • Esters have the carbonyl group that is polar but doesn't have the OH group (like carboxylic acid and alcohols have)
  • As a result, esters can't form hydrogen bonds with each other and have lower boiling points than carboxylic acids and alcohols

Naming:
Example: Name the following molecule

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Carboxylic acid + alcohol -> ester + water


Wize Concept
To name an ester:
1. The first part of the name comes from the alcohol. Ignore the O atom and name the alkyl chain (ex. methyl, ethyl, propyl, etc)
2. Find the part of the ester that came from the carboxylic acid. Count the longest chain of carbon atoms. Take the parent chain name, drop the "e" and add "oate" to the ending (ex. butanoate).
2. a) If there are substituents on the part that came from the carboxylic acid, name them before the main chain with the carboxylic acid.

The name of the ester will be in this form:
(alkyl chain that came from alcohol) SPACE (#)-(substituent on part from carboxylic acid)(name of parent chain that came from the carboxylic acid with the oate ending)

Name the ester above:
pentyl ethanoate

Example: Name the following molecule


ethyl 2-ethylbutanoate
Name the following molecule:

Name the following molecule: