Basic Organic Nomenclature

An Introduction

Dave Woodcock,
Associate Professor Emeritus UBC (Okanagan)
©1996,2000, 2008

5. Functional Groups
with Suffix or Prefix

VIII Alkyl Alkanoates
(esters)

Index


Atomic grouping
Suffix-oate
Prefix-
Position in chainonly at
end of chain
General formula CnH2nO2
Common family name ester

Notes:

  • Since the suffix (-oate) has an initial vowel, the terminal -e of the alkane name is dropped before the suffix is added.

  • Esters have two carbon chains separated by an 'ether' oxygen. Both these chains must be named separately in the full ester name which appears as two separate words in the form alkyl alkanoate. The alkyl part of the name is given to the chain without the carbonyl group. The alkanoate part of the name is given to the carbon chain which includes the carbonyl group: for this part it is as if the -oic acid with the hydrogen on the oxygen has been substituted to give the -oate. These designations are given without recourse to which is the longer chain. It is the position of the carbonyl group which dictates which is alkyl and which is alkanoate.

  • For the second time the IUPAC name consists of two words, there being a space between the word 'alkyl' and the word 'alkanoate'.

  • The carbonyl group in the alkanoate family is always at the end of a carbon chain and as such is always position 1. As with the alkanals, alkanamides, and alkanoic acids the locant (1) is omitted on the alkanoate part of the name.

  • The carbon chain not containing the carbonyl group may be attached at any carbon in the chain and so must have a locant when isomers are possible. Note that the locant is placed immediately before the -yl ending: e.g. hept-2-yl in the following.

    hept-2-yl butanoate.

    Examples :

    StructureIUPAC NameModel
    methyl methanoate
    ethyl methanoate
    methyl ethanoate
    methylpropanoate
    ethyl hexanoate
    cyclohexyl ethanoate
    but-2-yl 3-methylpentanoate
    2,4-dimethylpent-3-yl 3-methylbutanoate
    diethyl pentanedioate

Self Assignment Questions
Review Alkanoic acids

Next page : Aromatics I Monosubstituted Benzenes

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