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Organic Chemistry Nomenclature - Carboxylic Acids

Organic Chemistry Nomenclature - Carboxylic Acids

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Organic Nomenclature
Carboxylic Acids and DerivativesSpring 2006
Single carboxylic acids
Carboxylic acid nomenclature is very tough for a couple of reasons. First, mostcarboxylic acids are called by their common names. These names do not allow you toidentify the structure. Secondly, there is the IUPAC method for naming carboxylic acids.The stated IUPAC method for naming carboxylic acids is to drop the -e ending of thecorresponding alkane and add –oic acid. Finally, many compounds are called acids thatare not carboxylic acids. Some examples of each method are given below. IUPAC nameswill be in
italics
.
H OHO
 
OHO
 
OHO
 
OHO
 
Methanoic acid Ethanoic acid Propanoic acid Butanoic acid 
Formic acid Acetic acid Propionic acid Butyric acid
OHOOH
 
OHOOH
 
OHO
 
2-Hydroxypropanoic acid 
 
2-Hydroxy-2-phenylethanoic acid Propenoic acid 
 Lactic acid Mandelic acid Acrylic acid
NHNHHOHO
 
HHHHOHOHHH
 
9,10-didehydro-6-methyl 
 
1a,2,2a,5,5a,7a,7b,7c-octahydro-5-phenyl-1H-cyclo
 
ergoline-8-carboxylic acid 
 
but[bc]acenaphthylene-1-acetic acid 
Lysergic Acid Endiandric acid A
Double carboxylic acids
 
 
There are many ways to remember the dicarboxylic acids. My favorite is “Oh MySuch Good Apple Pie.”
HOOHOO
 
HOOOHO
 
HOOOHO
 
 Ethanedioic acid 
 
 Propanedioic acid 
 
 Butanedioic acid 
 Oxalic acid Malonic acid Succinic acidOH MY SUCH
HOOOHO
 
HOOOHO
 
 Pentanedioic acid 
 
 Hexanedioic acid 
 Glutaric acid Adipic acidGOOD APPLE
Salts of carboxylic acids
Salts of carboxylic acids are made by deprotonation of the carboxylic acid(s). TheIUPAC rule is to drop the ic or oic acid and add the suffix –ate.
OO
 Na
+
 
OO
+
OO
 Na
+
HOONH
2
 
Sodium acetate
 
 Potassium benzoate
 
Monosodium glutamate (MSG)
 
Compounds that are called acids even though they are not carboxylic acids
There are many compounds that are called acids even though they are notcarboxylic acids. I have included a few examples below.
OO OO
 
O OHO OH
 
OOHOHOOHHO
 Meldrum’s acid Squaric acid Ascorbic acid
Acid Chlorides
 
Acid halides are named by replacing –ic acid endings with –yl followed by theappropriate halide. Some examples are shown below.
ClO
 
Br OF
 
 Acetyl chloride
 
 p-Fluorobenzoyl bromide
 
Acid Anhydrides
Acid anhydrides are named by replacing acid with anhydride. If the acyl groupsare different, the groups are listed in alphabetical order. Some examples are shown below. Anhydrides are made from two carboxylic acids with water removed which iswhy they are called anhydrides.
OO O
 
OO O
 
OOO
 
 Acetic anhydride
 
 Acetic Benzoic anhydride
 
Maleic anhydride
 
Esters
Esters have two names. The first name is the alkyl group attached to the sp3hybridized oxygen. The second name is of the carboxylic acid portion. The –ic or –oicacid is dropped from this portion and replaced with –ate. Some examples follow.
OO
 
OO
 
OO
 
 Ethyl acetate
 
Methyl benzoate
 
 Phenyl acetate
 The (CAINE)s are esters. (Cocaine, Novocain)
NOOOO
 
NOOH
2
N
 Cocaine (free base) Novacain

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