Doc Brown's Chemistry  Revising Level Advanced Organic Chemistry

Part 6 CARBOXYLIC ACIDS and DERIVATIVES

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

How do you name carboxylic acids? How to name acid chlorides (acyl chlorides)? How to name amides? How to \name esters? How to name amino acids? Examples of displayed formula of carboxylic acids, esters, amides, acid chlorides, acid anhydrides, graphic formula, molecular formula, skeletal formula, structural formula, all of them named and nomenclature explained.

Organic Chemistry Part 6 sub-index: Acid .. Chloride .. Amide .. Ester .. Anhydride .. Substituted Acids and (i) mono carboxylic acids and their derivatives (ii) aliphatic saturated/unsaturated dicarboxylic acids (iii) aromatic acids and their derivatives

Introduction to naming aliphatic carboxylic acids and their derivatives

 1. How do you name 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. How do you name ACYL or ACID CHLORIDES? The primary suffix name for an acid chloride 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. How do you name ACYL or ACID AMIDES? 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. How do you name ESTER? Esters have the -COOC- bond system. The prefix part of the name of an ester is derived from the alkyl (or aryl) part of the alcohol (or phenol). The suffix part of the ester 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. How do you name ACYL or ACID ANHYDRIDES?

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. How do you name SUBSTITUTED CARBOXYLIC ACIDS? The possible positions of the substituent(s) in an aliphatic carboxylic acid are denoted by carbons 2,3,4 etc. 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 in (italics).

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

1b. methanamide (formamide), , , ,

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

an isomer of this is HCOOCH(CH₃)₂  1-methylethyl methanoate derived from methanoic acid and propan-2-ol

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), , , ,

an isomer of this is CH₃COOCH(CH₃)₂  1-methylethyl ethanoate derived from ethanoic acid and propan-2-ol

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

2j. aminoethanoic acid (aminoacetic acid), , ,

2k. hydroxyethanoic acid (hydroxyacetic acid), HO-CH₂-COOH, HOCH₂COOH

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

3c. propanamide (propionamide), , ,

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

an isomer of this is CH₃CH₂COOCH(CH₃)₂  1-methylethyl propanoate derived from propanoic acid and propan-2-ol

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

3n. 2-hydroxypropanoic acid, CH₃CH(OH)COOH

3o. 3-hydroxypropanoic acid, HO-CH₂-CH₂-COOH, HOCH₂CH₂COOH

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

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

an isomer of this is CH₃CH₂CH₂COOCH(CH₃)₂  1-methylethyl butanoate derived from butanoic acid and propan-2-ol

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

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

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

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

keywords formulae: how to name naming nomenclature empirical molecular formula graphic formula displayed formula skeletal formula structural isomers isomerism Acid .. Chloride .. acid acyl Amide .. Ester .. acid Anhydride .. Substituted carboxylic Acids and (i) mono carboxylic acids and their derivatives (ii) aliphatic saturated/unsaturated dicarboxylic acids (iii) aromatic acids and their derivatives HCOOH HCONH2 HCOOCH3 HCOOCH2CH3 HCOOCH2CH2CH3 CH3COOH HOCH2COOH CH3COCl CH3CONH2 (CH3CO)2O CH3COOCH3 CH3COOCH2CH3 CH3COOCH2CH2CH3 CH3COOC6H5 ClCH2COOH H2NCH2COOH C2H5COOH CH3CH2COOH CH3CHOHCOOH CH3CH (OH)COOH HOCH2CH2COOH CH3CH2COCl CH3CH2CH2CONH2 (CH3CH2CO)2O CH3CH2COOCH3 CH3CH2COOCH2CH3 CH3CH2COOCH2CH2CH3 CH3CHClCOOH ClCH2CH2COOH H2NCH2CH2COOH CH3CH(NH2)COOH (CH3)2CHCOOH CH2=CHCOOH C3H7COOH CH3CH2CH2COOH CH3CH2CH2CH2COCl CH3CH2CH2CH2CONH2 CH3CH2CH2CH2COOCH3 CH3CH2CH2CH2COOCH2CH3 CH3CH2CH2CH2COOCH2CH2CH3 CH3CH2CH2CH2COOH CH3(CH2)3COOH CH3(CH2)4COOH HOOCCOOH (COOH)2 HOOCCH2COOH CH2(COOH)2 HOOC-CH=CH-COOH HOOCCH=CHCOOH C6H5COOH CH3C6H4COOH C6H5COCl C6H5CONH2 C6H5COOCH3 C6H5COOCH2CH3 C6H5COOCH2CH2CH3 HOC6H4COOH HCOOCH(CH3)2 CH3COOCH(CH3)2 CH3CH2COOCH(CH3)2 CH3CH2CH2COOCH(CH3)2

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