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The Structure & Nomenclature (naming) of Carboxylic Acids and their Derivatives

 GCE-AS-A2-IB ADVANCED LEVEL ORGANIC CHEMISTRY

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organic identity tests * summary of functional groups and homologous series

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multiple choice quiz naming on RCOOH's & derivatives

type in name quiz on RCOOH's and derivatives

page sub-index: Acid .. Chloride .. Amide .. Ester .. Anhydride .. Substituted Acids

(i) mono carboxylic acids and their derivatives (ii) aliphatic saturated/unsaturated dicarboxylic acids (iii) aromatic acids and their derivatives

 1. CARBOXYLIC ACIDS: The primary suffix name for a carboxylic acid is based on the "longest carbon chain name *" + "oic acid" for the COOH acidic bond system e.g. methanoic acid, ethanoic acid etc. Note: Types 2. to 5. are carboxylic acid derivatives where the OH group is replaced by another group. [* without the end 'e'] 1st example methanoic acid

 2. ACID or ACYL CHLORIDE: The primary suffix name for an acid or acyl chloride is based on the "longest carbon chain name *" + "oyl chloride" for the COCl bond system e.g. ethanoyl chloride, propanoyl chloride etc. (there is no stable methanoyl chloride). [* without the end 'e'] 1st example ethanoyl chloride

 3. ACID AMIDE: The primary suffix name for an acid amide is based on the "longest carbon chain name *" + "amide" for the CONH₂ bond system e.g. methanamide, ethanamide etc. [* without the end 'e'] 1st example methanamide

 4. ESTER: Esters have the -COOC- bond system. The prefix part of the name is derived from the alkyl (or aryl) part of the alcohol (or phenol). The suffix part of the name is based on the carboxylic acid, but the "…oic acid" becomes "…oate" e.g. ethyl ethanoate, methyl ethanoate, pentyl butanoate etc. (lots of isomeric permutations as the total C number rises). In the diagram, the R group is derived from the carboxylic acid and the R' group from the alcohol or phenol. 1st example methyl methanoate

 5. ACID ANHYDRIDE: The primary suffix name for an acid anhydride is the "longest carbon chain name *" + "anhydride" for the (CO)₂O bond system e.g. ethanoic anhydride, propanoic anhydride etc. [Note: (a) * without the end 'e'; (b) there is no stable methanoic anhydride; (b) an acid anhydride is equal to two carboxylic acid molecules minus a water molecule e.g. 2 RCOOH - H₂O = (RCO)₂O. 1st example ethanoic anhydride

 6. SUBSTITUTED CARBOXYLIC ACIDS: The possible positions of the substituent(s) are denoted by carbons 2,3,4 etc. with with a prefix e.g. amino, hydroxy, halo… or alkyl… groups etc., and using the lowest possible numbers. The 'lowest' numbers are determined by assigning number 1 to the carbon of the carboxylic acid (or other derived) group at the end of the longest C atom chain . If there is more than one 'type' of substituent e.g. using the prefixes: bromo…, chloro…, methyl… etc., they are written out in alphabetical order irrespective of carbon atom number (note: di, tri are ignored in using this rule) e.g. 2-chloropropanoic acid CH₃CHClCOOH. 1st example chloroethanoic acid

In order of 1. methanoic, 2. ethanoic, 3. propanoic, 4. butanoic, 5. pentanoic, 6. hexanoic

and some 'old' names are quoted.

1a. methanoic Acid (formic acid), , , ,

1b. methanamide (formamide), , , ,

1c. methyl methanoate (methyl formate), , , ,

2a. ethanoic acid (acetic acid), , , ,

2b. ethanoyl chloride (acetyl chloride), , , ,

2c. ethanamide (acetamide), , , ,

2d. ethanoic anhydride (acetic anhydride), , ,

2e. methyl ethanoate (methyl acetate), , , ,

2f. ethyl ethanoate (ethyl acetate), , , ,

2i. chloroethanoic acid (chloroacetic acid), , ,

3a. propanoic acid  (propionic acid), , ,

3c. propanamide (propionamide), , ,

3e. methyl propanoate (methyl propionate), , ,

3m. propenoic acid (acrylic acid), CH₂=CH-COOH, an unsaturated mono carboxylic acid

4a. butanoic acid (butyric acid), , ,

4e. methyl butanoate (methyl butyrate), , ,

1. ethanedioic acid (oxalic acid), , , ,

2. propanedioic acid (malonic acid), , , ,

3. butanedioic acid (succinic acid), , , ,

(ii)(b) Examples of aliphatic unsaturated dicarboxylic acids

1. But-2-ene-1,4-dioic acid, HOOC-CH=CH-COOH, which has the geometrical isomers

cis-but-2-ene-1,4-dioic acid, (maleic acid)  

and trans-but-2-ene-1,4-dioic acid, (fumaric acid)

2.

more details on geometrical isomerisim of these acids

5a. , 2-hydroxybenzenecarboxylic acid, 2-hydroxybenzoic acid (salicylic acid)

5b. 2-ethanoylhydroxybenzoic acid (acetylsalicylic acid, Aspirin)

5e. 2-, 3- or 4-methylbenzoic acid

GENERAL REVISION NOTES

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