Naming Acyl Chlorides

(Chemical) Definition of Acyl Chlorides - also known as Acid Chlorides:

Structure of acid chloride functional group

Acyl Chlorides are organic chemical compounds that include a -carbonyl group* (i.e. an oxygen atom attached to a carbon atom by a double covalent bond) and a chlorine atom attached to the carbon atom attached to the oxygen atom:

*a carbonyl group is a functional group consisting of a carbon atom double-bonded to an oxygen atom: C=O.

Acyl chloride molecules can vary in size up to very long molecules most of which consist of carbon atoms attached to each other and also to hydrogen atoms.

Names of Acyl Chlorides in General

Acyl chlorides are also known generically as acid chlorides (link to equivalent page about naming acid chlorides).

Acyl chlorides are named according to the same system as other organic compounds. In the simplest case of linear acyl chlorides, the suffix -oyl chloride is added to the stem used to indicate the number of carbon atoms in the longest chain within the molecule. That is, when naming acyl chlorides the first step is to consider the number of carbon atoms forming the longest chain within the molecule. The simplest situation is when all the carbon atoms in the molecule are attached together in a linear (i.e. unbranched) configuration. In that case the number of carbon atoms forming that single chain is the same as the total number of carbon atoms in the molecule. After identifying the longest carbon chain in the molecule use the number of carbon atoms forming that chain to look-up the most likely* stem of the name of the molecule using the same system as used for naming alkanes (see also the examples listed in the table below).

*Some organic compounds have multiple names so we refer to the 'most likely' stem of the name of the compound because some variants may also be referred to by older or simply non-standard names based on a slightly different stem - the 'synonyms' column in the table below for examples.

Rememer that if the carbon atoms do not form a linear chain but include branches, the longest linear chain of carbon atoms within the molecule usually determines the base of the standard name of the compound, onto which is added information about the branches incl. their lengths in terms of the number of carbon atoms in each branch (i.e. methyl- indicates a branch consisting of just one carbon atom attached to the main chain, ethyl- indicates a branch of two carbon atoms in length, etc.) and their positions along the longest linear carbon chain (e.g. attached to the 2nd carbon, 3rd carbon, etc.).

The simplest linear acyl chlorides are named and their structures shown in the following table.

Names and Structures of simple Linear Acyl Chlorides

The first ten members of the homologous series of linear acyl chlorides are represented below. The simple structures drawn below show bond types such as single and double bonds, but not accurate bond angles.

  • Formyl chloride (CHClO)
    Simple Formula:
    Simple Structure:
    Structure of formyl chloride
  • Ethanoyl chloride (C2H3ClO)
    Simple Formula:
    Simple Structure:
    Structure of ethanoyl chloride
    *Examples of other / previous names:
    • acetyl chloride
    • acetic chloride
    • acetylchloride
    • acetic acid, chloride
  • Propanoyl chloride (C3H5ClO)
    Simple Formula:
    Simple Structure:
    Structure of propanoyl chloride
    *Examples of other / previous names:
    • propionyl chloride
    • propionic chloride
    • propionic acid chloride
  • Butanoyl chloride (C4H7ClO)
    Simple Formula:
    Simple Structure:
    Structure of butanoyl chloride
    *Examples of other / previous names:
    • butyryl chloride
    • butyric chloride
    • butyroyl chloride
    • butyric acid chloride
    • n-butyryl chloride
  • Pentanoyl chloride (C5H9ClO)
    Simple Formula:
    Simple Structure:
    Structure of pentanoyl chloride
    *Examples of other / previous names:
    • valeryl chloride
  • Hexanoyl chloride (C6H11ClO)
    Simple Formula:
    Simple Structure:
    Structure of hexanoyl chloride
    *Examples of other / previous names:
    • n-hexanoyl chloride
    • caproyl chloride
  • Heptanoyl chloride (C7H13ClO)
    Simple Formula:
    Simple Structure:
    Structure of heptanoyl chloride
    *Examples of other / previous names:
    • n-heptanoyl chloride
  • Octanoyl chloride (C8H15ClO)
    Simple Formula:
    Simple Structure:
    Structure of octanoyl chloride
    *Examples of other / previous names:
    • n-octanoyl chloride
    • capryloyl chloride
    • octanoic chloride
    • caprylyl chloride
    • caprylic acid chloride
    • octanoic acid chloride
  • Nonanoyl chloride (C9H17ClO)
    Simple Formula:
    Simple Structure:
    Structure of nonanoyl chloride
    *Examples of other / previous names:
    • n-nonanoyl chloride
    • pelargonoyl chloride
    • nonanoic acid chloride
  • Decanoyl chloride (C10H19ClO)
    Simple Formula:
    Simple Structure:
    Structure of decanoyl chloride
    *Examples of other / previous names:
    • n-decanoyl chloride

* The synonyms indicated for compounds listed above are just some examples of alternative names found online and believed to have been used to refer to the substance indicated. They have not all been verified and may include common (non-scientific) names and trade names specific to particular suppliers. The purpose of these lists is to give a general indication of the range of names by which these acyl chlorides are, or have been, known.

In the News:

Packaged food healthiest in the UK, USA, Australia and Canada - 22 Aug '19

Garlic and Artichoke adopted through ABC's Adopt-an-Herb Program - 14 Jun '19

Cranberry Harvest underway in USA - 5 Oct '18

By 2043 obesity might exceed smoking as the largest preventable cause of cancer in women - 25 Sep '18

Total retail sales of herbal supplements in the USA exceeded $8 Billion in 2017 - 13 Sep '18

It's a bumper blueberry season - 13 Jul '18

Heat-related health concerns for older adults increase during the summer - 28 Jun '18

U.S. FDA takes steps to advance health through improvements in nutrition - 27 Jun '18

Melchisadec is associated with peace, spirituality and a powerful violet ray of spiritual energy.

Although care has been taken when compiling this page, the information contained might not be completely up to date. Accuracy cannot be guaranteed. This material is copyright. See terms of use.

IvyRose Holistic 2003-2019.