DOC BROWN'S Science-CHEMISTRY HOMEPAGE KS3 SCIENCE QUIZZES and WORKSHEETS (~US grades 6-8)
GCSE SCIENCE help links GCSE ADDITIONAL SCIENCE help links
KS3 BIOLOGY Quizzes KS3 CHEMISTRY Quizzes & Worksheets KS3 PHYSICS Quizzes
KS4 Science GCSE/IGCSE CHEMISTRY NOTES (~US grades 8-10) KS4 Science GCSE/IGCSE CHEMISTRY QUIZZES and WORKSHEETS (~US grades 8-10) ADVANCED LEVEL CHEMISTRY QUIZZES and WORKSHEETS (~US grades 11-12)
Custom Search

Doc Brown's Chemistry  Revising Level Advanced Organic Chemistry

Part 6 CARBOXYLIC ACIDS and DERIVATIVES

(c) doc b (c) doc b (c) doc b (c) doc b (c) doc b (c) doc b

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

Carboxylic acid nomenclature - names & structures of carboxylic acids and derivatives and substituted derivatives of carboxylic acids - 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? how to name amides? How to name substituted carboxylic 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

(c) doc b 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

  

(c) doc b 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

  

(c) doc b 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

  

(c) doc b 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.

The first part of an ester's name is derived from the alcohol e.g. methyl from methanol, ethyl from ethanol and propyl from propanol etc. The second part of the name comes from the carboxylic acid and ends in ...oate e.g. methanoate from methanoic acid, ethanoate from ethanoic acid and propanoate from propanoic acid etc.

 

(c) doc b 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

  

(c) doc b 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


(i) Examples of mono carboxylic acids and their derivatives

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), (c) doc b,(c) doc b ,(c) doc b , (c) doc b

1b. methanamide (formamide), (c) doc b,(c) doc b ,(c) doc b , (c) doc b

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

1d. ethyl methanoate , (c) doc b,(c) doc b ,(c) doc b , (c) doc b

1e. propyl methanoate , (c) doc b,(c) doc b , (c) doc b

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


2a. ethanoic acid (acetic acid), (c) doc b,(c) doc b ,(c) doc b , (c) doc b

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

2c. ethanamide (acetamide), (c) doc b,(c) doc b ,(c) doc b , (c) doc b

2d. ethanoic anhydride (acetic anhydride), (c) doc b,(c) doc b , (c) doc b

2e. methyl ethanoate (methyl acetate), (c) doc b,(c) doc b , (c) doc b, (c) doc b

2f. ethyl ethanoate (ethyl acetate), (c) doc b,(c) doc b ,(c) doc b , (c) doc b

2g. propyl ethanoate , (c) doc b ,(c) doc b , (c) doc b

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

2h. phenyl ethanoate , CH3COOC6H5(c) doc b

2i. chloroethanoic acid (chloroacetic acid), (c) doc b, (c) doc b, (c) doc b

2j. aminoethanoic acid (aminoacetic acid), (c) doc b, (c) doc b, (c) doc b

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


3a. propanoic acid  (propionic acid), (c) doc b, (c) doc b, (c) doc b

3b. propanoyl chloride , (c) doc b, (c) doc b, (c) doc b

3c. propanamide (propionamide), (c) doc b, (c) doc b, (c) doc b

3d. propanoic anhydride , (c) doc b, (c) doc b, (c) doc b

3e. methyl propanoate (methyl propionate), (c) doc b, (c) doc b, (c) doc b

3f. ethyl propanoate, (c) doc b, (c) doc b, (c) doc b

3g. propyl propanoate, (c) doc b, (c) doc b, (c) doc b

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

3h. 2-chloropropanoic acid , (c) doc b, (c) doc b, (c) doc b

3i. 3-chloropropanoic acid , (c) doc b, (c) doc b, (c) doc b

3j. 2-aminopropanoic acid, (c) doc b, (c) doc b, (c) doc b

3k. 3-aminopropanoic acid,(c) doc b ,(c) doc b , (c) doc b

3l. 2-methylpropanoic acid, (c) doc b,(c) doc b , (c) doc b

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

3p. 2-hydroxypropanenitrile, CH3CH(OH)CN,


4a. butanoic acid (butyric acid), (c) doc b, (c) doc b, (c) doc b

4b. butanoyl chloride, (c) doc b, (c) doc b, (c) doc b

4c. butanamide, (c) doc b, (c) doc b, (c) doc b

4d. butanoic anhydride, (c) doc b, (c) doc b

4e. methyl butanoate (methyl butyrate), (c) doc b, (c) doc b, (c) doc b

4f. ethyl butanoate , (c) doc b, (c) doc b, (c) doc b

4g. propyl butanoate , (c) doc b, (c) doc b, (c) doc b

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

4h. butyl butanoate , (c) doc b, (c) doc b(c) doc b

4i. 2-methylbutanoic acid , (c) doc b, (c) doc b

4j. 3-methylbutanoic acid , (c) doc b, (c) doc b

4k. 2-hydroxybutanoic acid ,(c) doc b , (c) doc b

4l. 3-hydroxybutanoic acid ,(c) doc b , (c) doc b

4m. 4-hydroxybutanoic acid ,(c) doc b , (c) doc b

4n. 2-chlorobutanoic acid ,(c) doc b , (c) doc b

4o. 3-chlorobutanoic acid ,(c) doc b , (c) doc b

4p. 4-chlorobutanoic acid ,(c) doc b , (c) doc b

4q. 2-hydroxy-2-methylbutanenitrile,


5a. pentanoic acid , (c) doc b, (c) doc b, (c) doc b

5b. pentanoyl chloride , (c) doc b, (c) doc b, (c) doc b

5c. pentanamide , (c) doc b, (c) doc b, (c) doc b

5d. pentanoic anhydride , (c) doc b, (c) doc b

5e. methyl pentanoate , (c) doc b, (c) doc b, (c) doc b

5f. ethyl pentanoate , (c) doc b, (c) doc b , (c) doc b

5g. propyl pentanoate , (c) doc b, (c) doc b , (c) doc b

5h. butyl pentanoate , (c) doc b, (c) doc b

5i. 2-methylpentanoic acid , (c) doc b, (c) doc b

5j. 3-methylpentanoic acid , (c) doc b, (c) doc b

5k. 4-methylpentanoic acid , (c) doc b, (c) doc b

5l. 2-ethylpentanoic acid , (c) doc b, (c) doc b

5m. 3-ethylpentanoic acid , (c) doc b, (c) doc b


6a. hexanoic acid , (c) doc b, (c) doc b , (c) doc b

6b. 2-methylhexanoic acid , (c) doc b, (c) doc b

6c. 3-methylhexanoic acid , (c) doc b, (c) doc b

6d. 4-methylhexanoic acid , (c) doc b, (c) doc b

6e. 5-methylhexanoic acid , (c) doc b, (c) doc b

6f. 2-ethylhexanoic acid , (c) doc b, (c) doc b

6g. 3-ethylhexanoic acid , (c) doc b, (c) doc b

6h. 4-ethylhexanoic acid , (c) doc b, (c) doc b


(ii)(a) Examples of aliphatic saturated dicarboxylic acids

1. ethanedioic acid (oxalic acid), (c) doc b, (c) doc b, (c) doc b, (c) doc b

2. propanedioic acid (malonic acid), (c) doc b, (c) doc b, (c) doc b, (c) doc b

3. butanedioic acid (succinic acid), (c) doc b, (c) doc b, (c) doc b, (c) doc b

(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) (c) doc b  (cis)

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

2. ...

more details on geometrical isomerisim of these acids


(iii) Examples of aromatic acids and their derivatives

The -COOH is directly attached to the benzene ring

1. (c) doc b, (c) doc b, (c) doc b, (c) doc b, benenecarboxylic acid, benzoic acid

2. (c) doc b, (c) doc b, (c) doc b, (c) doc b, benzenecarbonyl chloride, benzoyl chloride

3. (c) doc b,(c) doc b , (c) doc b,(c) doc b, benzenecarboxamide, benzamide,

4a. (c) doc b, (c) doc b, (c) doc b, methyl benzenecarboxylate, methyl benzoate

4b. (c) doc b, (c) doc b, (c) doc b, ethyl benzenecarboxylate, ethyl benzoate

4c. (c) doc b, (c) doc b, (c) doc b, propyl benzenecarboxylate, propyl benzoate

4d.  C6H5COOC6H5 , (c) doc b phenyl benzoate

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

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

5c. (c) doc b, 3-hydroxybenzenecarboxylic acid, 3-hydroxybenzoic acid

5d. (c) doc b, 4-hydroxybenzenecarboxylic acid, 4-hydroxybenzoic acid

5e. (c) doc b(c) doc b(c) doc b2-, 3- or 4-methylbenzoic acid

6a. (c) doc b, benzene-1,2-dicarboxylic acid

6b. (c) doc b, benzene-1,3-dicarboxylic acid

6c. (c) doc b, benzene-1,4-dicarboxylic acid


LINKS TO ASSOCIATED ADVANCED ORGANIC CHEMISTRY PAGES

Multiple choice quiz on naming carboxylic acids and derivatives

(c) doc bType in name (short answer) quiz on carboxylic acids and derivatives

All Advanced Organic Chemistry Notes

Summary of Organic Functional Groups Notes

Quiz on Organic Structure Recognition

Summary of organic chemistry functional group tests

Intermolecular forces & boiling points of carboxylic acids compared to other organic molecules

The shapes and bond angles of simple organic molecules

 


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


A level Revision notes for GCE Advanced Subsidiary Level AS Advanced Level A2 IB Revise AQA GCE Chemistry OCR GCE Chemistry Edexcel GCE Chemistry Salters Chemistry CIE Chemistry, WJEC GCE AS A2 Chemistry, CCEA/CEA GCE AS A2 Chemistry revising courses for pre-university students (equal to US grade 11 and grade 12 and AP Honours/honors level courses) Cambridge University Chemistry courses Oxford University Chemistry courses Durham University Chemistry courses St Andrews University Chemistry courses Bristol University Chemistry courses Imperial College London University Chemistry courses York University Chemistry courses Warwick University Chemistry courses Edinburgh University Chemistry courses Manchester University Chemistry courses Southampton University Chemistry courses Sheffield University Chemistry courses University College London University Chemistry courses Nottingham University Chemistry courses Surrey University Chemistry courses Heriot-Watt University Chemistry courses Glasgow University Chemistry courses Leeds University Chemistry courses Strathclyde University Chemistry courses Bath University Chemistry courses Liverpool University Chemistry courses Birmingham University Chemistry courses East Anglia University Chemistry courses Sussex University Chemistry courses Cardiff University Chemistry courses Hull University Chemistry courses Leicester University Chemistry courses Keele University Chemistry courses Newcastle University Chemistry courses Queen's, Belfast University Chemistry courses Reading University Chemistry courses Loughborough University Chemistry courses Huddersfield University Chemistry courses Bangor University Chemistry courses Aberdeen University Chemistry courses Plymouth University Chemistry courses Central Lancashire University Chemistry courses Aston University Chemistry courses Robert Gordon University Chemistry courses Queen Mary University Chemistry courses Kent University Chemistry courses Sheffield Hallam University Chemistry courses Liverpool John Moores University Chemistry courses Bradford University Chemistry courses Teesside University Chemistry courses Glamorgan University Chemistry courses Nottingham Trent University Chemistry courses Brighton University Chemistry courses Greenwich University Chemistry courses Northumbria University Chemistry courses Kingston University Chemistry courses Coventry University Chemistry courses West of Scotland University Chemistry courses Manchester Metropolitan University Chemistry courses London Metropolitan University Chemistry courses Abertay Dundee University Chemistry courses  A Level AQA Edexcel OCR Salters Chemistry revision Advanced Level chemistry courses University Chemistry courses


Website content copyright © Dr Phil Brown 2000–2014 All rights reserved on revision notes, images, puzzles, quizzes, worksheets, x–words etc. * Copying of website material is not permitted * chemhelp@tiscali.co.uk

Alphabetical Index for Science Pages Content A B C D E F G H I J K L M N O P Q R S T U V W X Y Z

SITE HELP SEARCH - ENTER SPECIFIC WORDS/FORMULA etc.