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Advanced A Level Organic Chemistry: Carboxylic acids & derivatives: naming & structure
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6.1 The molecular structure & nomenclature - naming of carboxylic acids and derivatives Doc Brown's Chemistry Advanced Level Pre-University Chemistry Revision Study Notes for UK KS5 A/AS GCE IB advanced level organic chemistry students US K12 grade 11 grade 12 organic chemistry Part 6 CARBOXYLIC ACIDS and DERIVATIVES
Organic Chemistry Part 6.1 sub-index for this page:
Abbreviations used: mpt = melting point; bpt = boiling point; dec = thermally decomposes INDEX of all My carboxylic acids and derivatives notes
All My Advanced A Level Organic
Chemistry Notes
Index of My GCSE/IGCSE Oil - useful products
and basic organic chemistry notes This page covers aliphatic carboxylic acids IUPAC nomenclature acyl/acid chlorides IUPAC nomenclature acyl/acid amides IUPAC nomenclature esters IUPAC nomenclature carboxylic acid anhydride IUPAC nomenclature substituted carboxylic acids, mono carboxylic acids and their derivatives, aliphatic saturated dicarboxylic acids, unsaturated dicarboxylic acids, aromatic carboxylic acids and their derivatives Introduction to naming aliphatic carboxylic acids and their derivatives
Note: For RCOCl there is no HCOCl, unstable acid chloride,
-COOH is the carboxyl (carboxylic acid) functional group of the homologous series of 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. The prefix of the IUPAC name comes from the parent alkane without the end 'e', to which is added ...oic acid. The e is retained for dicarboxylic acids and prefixed to ...dioic acid. Aromatic carboxylic acids are named from the parent aromatic hydrocarbon. Note: Types 2. to 5. are carboxylic acid derivatives where the OH group is replaced by another group. 1st example methanoic acid. Aromatic acids have the same functional group, but directly attached to a benzene (aromatic) ring and are therefore named on the basis of being an 'aromatic' compound.
aliphatic carboxylic acid
-COCl is the functional group of the homologous series of acid/acyl 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). 1st example ethanoyl chloride The prefix of the IUPAC name comes from the parent alkane without the end 'e', to which is added ...oyl chloride] aliphatic carboxylic acid chlorides (acyl chlorides)
aromatic acid chloride
-CONH2 is the functional group of the homologous series of acid/acyl 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. 1st example methanamide. The prefix of the IUPAC name comes from the parent alkane without the end 'e', to which is added ...amide. aliphatic acid amide
aromatic acid amide
-COOC is the functional group of the homologous series of carboxylic acid esters. 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 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. The prefix of the IUPAC name comes from the parent alkane without the end 'e', to which is added ...oic anhydride] aliphatic acid anhydride
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: amino..., bromo…, chloro…, hydroxy ..., 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 aliphatic mono-substituted aliphatic acids 3-aminopropanoic acid , 7. How do you name nitriles? The nitrile functional group consists of a carbon to nitrogen triple bond. The name is based on the longest carbon chain, including the C of the nitrile group. methanenitrile (methanonitrile, hydrogen
cyanide),
ethanenitrile (ethanonitrile,
acetonitrile), C2H3N, propanenitrile (propanonitrile, ethyl
cyanide), C3H5N,
2-hydroxypropanenitrile, CH3CH(OH)CN,
2-hydroxy-2-methylpropanenitrile
2-hydroxy-2-methylbutanenitrile,
(i) Examples of mono carboxylic acids and their derivatives
1a. methanoic Acid
(formic acid), molecular formula CH2O2, structural
formulae
1b. methanamide
(formamide), molecular formula CH3NO,
structural formula
1c. methyl methanoate
(methyl formate), C2H4O2, structural
formula
1d. ethyl methanoate,
molecular formula C3H6O2, structural formulae
1e. propyl methanoate,
molecular formula C4H8O2, abbreviated structural formulae
2a. ethanoic acid
C2H4O2,
(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), 2g. propyl ethanoate ,
2h. phenyl ethanoate , CH3COOC6H5
, 2i. chloroethanoic acid
(chloroacetic acid), 2j. aminoethanoic acid (aminoacetic acid), 2k. hydroxyethanoic acid (hydroxyacetic acid), HO-CH2-COOH, HOCH2COOH (2-hydroxyethanoic acid, but 2 not necessary) 3a. propanoic acid
(propionic acid), 3b. propanoyl chloride , 3c. propanamide
(propionamide), 3d. propanoic anhydride , 3e. methyl propanoate
(methyl propionate), 3f. ethyl propanoate, 3g. propyl propanoate,
3h. 2-chloropropanoic acid , 3i. 3-chloropropanoic acid , 3j. 2-aminopropanoic acid, 3k. 3-aminopropanoic acid, 3l. 2-methylpropanoic acid (isobutyric acid), 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,
3q. 2-hydroxypropanoic acid
3r. 2-hydroxy-2-methylpropane nitrile
3s. 2-hydroxy-2-methylpropanoic acid
4a. butanoic acid
(butyric acid), 4b. butanoyl chloride, 4c. butanamide, 4d. butanoic anhydride, 4e. methyl butanoate
(methyl butyrate), 4f. ethyl butanoate , 4g. propyl butanoate ,
4h. butyl butanoate , 4i. 2-methylbutanoic acid , 4j. 3-methylbutanoic acid , 4k. 2-hydroxybutanoic acid , 4l. 3-hydroxybutanoic acid , 4m. 4-hydroxybutanoic acid , 4n. 2-chlorobutanoic acid , 4o. 3-chlorobutanoic acid , 4p. 4-chlorobutanoic acid , 4q. 2-hydroxy-2-methylbutanenitrile,
4s. 2-hydroxy-2-methylbutanoic acid
5a. pentanoic acid , 5b. pentanoyl chloride , 5c. pentanamide , 5d. pentanoic anhydride , 5e. methyl pentanoate , 5f. ethyl pentanoate , 5g. propyl pentanoate , 5h. butyl pentanoate , 5i. 2-methylpentanoic acid , 5j. 3-methylpentanoic acid , 5k. 4-methylpentanoic acid , 5l. 2-ethylpentanoic acid , 5m. 3-ethylpentanoic acid , 6a. hexanoic acid , 6b. 2-methylhexanoic acid , 6c. 3-methylhexanoic acid , 6d. 4-methylhexanoic acid , 6e. 5-methylhexanoic acid , 6f. 2-ethylhexanoic acid , 6g. 3-ethylhexanoic acid , 6h. 4-ethylhexanoic acid , (ii)(a) Examples of aliphatic saturated dicarboxylic acids and a tricarboxylic acid 1. ethanedioic acid
(oxalic acid), 2. propanedioic acid
(malonic acid),
3. butanedioic acid
(succinic acid),
4. 2-hydroxybutanedioic acid (malic acid),
5. 2,3-dihydroxybutanedioic acid (tartaric
acid) ,
5.
(ii)(b) Examples of aliphatic unsaturated dicarboxylic acids 1. But-2-ene-1,4-dioic acid, HOOC-CH=CH-COOH, which has the geometric isomers Z-but-2-ene-1,4-dioic acid,
(maleic acid)
and
E-but-2-ene-1,4-dioic acid, (fumaric
acid) 2. ... more details on E/Z isomerism of these acids (iii) Examples of aromatic acids and their derivatives The -COOH is directly attached to the benzene ring 1.
2. 3. 4a. 4b. 4c. 4d.
C6H5COOC6H5
, 5a. 5b. 5c. 5d. 5e.
5f.
5g.
5h.
6a. 6b. 6c. Ethane-1,2-diol
(ethylene glycol, glycol),
C2H6O2, benzene-1,4-dicarboxylic acid forms a condensation polymer with ethane-1,2-diol, the polyester Terylene
AMINO ACIDS and ZWITTERIONS
Question - can you name these more complex substituted carboxylic acids
[ SEARCH BOX]INDEX of all My carboxylic acids and derivatives notes
All My Advanced A Level Organic
Chemistry Notes
Index of My GCSE/IGCSE Oil - useful products
and basic organic chemistry notes LINKS TO ASSOCIATED ADVANCED ORGANIC CHEMISTRY PAGES
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 These detailed notes on the structure and naming of carboxylic acids include the general formula of carboxylic acids molecules, empirical formula of carboxylic acid molecules, structural formula of carboxylic acid molecules, skeletal formula of carboxylic acid molecules, displayed formula of carboxylic acid molecules, shapes of carboxylic acid molecules, isomers of carboxylic acids molecule These detailed notes on the structure and naming of esters include the general formula of ester molecules, empirical formula of ester molecules, structural formula of ester molecules, skeletal formula of ester molecules, displayed formula of ester molecules, shapes of ester molecules, isomers of esters molecules These detailed notes on the structure and naming of acid amides include the general formula of amide molecules, empirical formula of amide molecules, structural formula of amide molecules, skeletal formula of amide molecules, displayed formula of amide molecules, shapes of amide molecules, isomers of amides molecules These detailed notes on the structure and naming of acid/acyl chlorides include the general formula of acid/acyl chloride molecules, empirical formula of acid/acyl chloride molecules, structural formula of acid/acyl chloride molecules, skeletal formula of acid/acyl chloride molecules, displayed formula of acid/acyl chloride molecules, shapes of acid/acyl chloride molecules, isomers of acid/acyl chlorides molecules IUPAC rules for carboxylic acid nomenclature. Students should be able to draw structural formula of carboxylic acids, displayed and skeletal formulas for carboxylic acid organic compounds apply IUPAC rules for nomenclature to name carboxylic acid organic compounds including chains and rings and be able to apply IUPAC rules for nomenclature to draw the structural, displayed or skeletal structure of carboxylic acid organic compounds from the carboxylic acid IUPAC name IUPAC rules for ester nomenclature. Students should be able to draw structural formula of ester, displayed and skeletal formulas for ester organic compounds apply IUPAC rules for nomenclature to name ester acid organic compounds including chains and rings and be able to apply IUPAC rules for nomenclature to draw the structural, displayed or skeletal structure of ester organic compounds from the ester IUPAC name from the homologous series of esters IUPAC rules for amide nomenclature. Students should be able to draw structural formula of amide, displayed and skeletal formulas for amide organic compounds apply IUPAC rules for nomenclature to name amide acid organic compounds including chains and rings and be able to apply IUPAC rules for nomenclature to draw the structural, displayed or skeletal structure of amide organic compounds from the amide IUPAC name from the homologous series of amides IUPAC rules for acyl/acid chloride nomenclature. Students should be able to draw structural formula of acyl/acid chloride, displayed and skeletal formulas for acyl/acid chloride organic compounds apply IUPAC rules for nomenclature to name acyl/acid chloride acid organic compounds including chains and rings and be able to apply IUPAC rules for nomenclature to draw the structural, displayed or skeletal structure of acyl/acid chloride organic compounds from the acyl/acid chloride IUPAC name from the homologous series of acyl/acid chlorides IUPAC rules for substituted carboxylic acids nomenclature. Students should be able to draw structural formula of substituted carboxylic acids, displayed and skeletal formulas for substituted carboxylic acids organic compounds apply IUPAC rules for nomenclature to name substituted carboxylic acids acid organic compounds including chains and rings and be able to apply IUPAC rules for nomenclature to draw the structural, displayed or skeletal structure of substituted carboxylic acids organic compounds from the substituted carboxylic acids IUPAC name from the homologous series of substituted carboxylic acids ANSWERS to the Question on naming more complex substituted carboxylic acids
The skeletal formula showing the molecular structure of (1) 3-methylpentanoic acid (2) 4-bromo-2-ethylpentanoic acid (3) 2,5-dimethylhexanoic acid (4) 4-chloro-3-hydroxyheptanoic acid and (6) 6-bromo-2-hydroxy-4-phenyloctanoic acid and watch out for numbering, the C of COOH is 1 and note the alphabetical order of substituents |
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