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Carboxylic Acids: Nomenclature & Reactions

The document discusses carboxylic acids and their derivatives. It provides the IUPAC nomenclature for common carboxylic acids from formic acid to stearic acid. Carboxylic acids are weak acids that form hydrogen bonds and exist as dimers. They can be prepared through oxidation of alcohols or alkylbenzenes, hydrolysis of nitriles, or carbonation of Grignard reagents. Derivatives of carboxylic acids include esters, acid chlorides, acid anhydrides, and amides. Nucleophilic acyl substitution and addition reactions are important reactions of these derivatives. Reduction with lithium aluminum hydride can convert derivatives to alcohols except for amides

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Biotechnology IIUM Kuantan
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24 views37 pages

Carboxylic Acids: Nomenclature & Reactions

The document discusses carboxylic acids and their derivatives. It provides the IUPAC nomenclature for common carboxylic acids from formic acid to stearic acid. Carboxylic acids are weak acids that form hydrogen bonds and exist as dimers. They can be prepared through oxidation of alcohols or alkylbenzenes, hydrolysis of nitriles, or carbonation of Grignard reagents. Derivatives of carboxylic acids include esters, acid chlorides, acid anhydrides, and amides. Nucleophilic acyl substitution and addition reactions are important reactions of these derivatives. Reduction with lithium aluminum hydride can convert derivatives to alcohols except for amides

Uploaded by

Biotechnology IIUM Kuantan
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PPT, PDF, TXT or read online on Scribd

CHAPTER 12

CARBOXYLIC
ACIDS
IUPAC Nomenclature of Carboxylic Acid

Carbon atoms Common name IUPAC name Chemical formula

1 Formic acid Methanoic acid HCOOH


2 Acetic acid Ethanoic acid CH3COOH

3 Propionic acid Propanoic acid CH3CH2COOH

4 Butyric acid Butanoic acid CH3(CH2)2COOH

5 Valeric acid Pentanoic acid CH3(CH2)3COOH

6 Caproic acid Hexanoic acid CH3(CH2)4COOH

7 Enanthic acid Heptanoic acid CH3(CH2)5COOH

8 Caprylic acid Octanoic acid CH3(CH2)6COOH

9 Pelargonic acid Nonanoic acid CH3(CH2)7COOH

10 Capric acid Decanoic acid CH3(CH2)8COOH

12 Lauric acid Dodecanoic acid CH3(CH2)10COOH

16 Palmitic acid Hexadecanoic acid CH3(CH2)14COOH

18 Stearic acid Octadecanoic acid CH3(CH2)16COOH


3,3-dimethylcyclohexane carboxylic acid
NOMENCLATURE OF THE THE SALTS OF CARBOXYLIC ACIDS
Physical properties
• A weak acid.
• Polar and form hydrogen bonds with each other, exist as
dimeric pairs

• Lower carboxylic acid (C1-C4) misible with water, >C5


less soluble due to the increasing of the R chain.
PREPARATIONS OF THE
CARBOXYLIC ACIDS
A) Oxidation of Alkybenzenes
B) Oxidation of primary alcoholS
c) Hydrolysis of Nitriles
d) Carbonation of Grignard Reagents
- the alkyl halide is converted to corresponding grignard reagent then
followed by treament with CO2.
- The product has more carbon than the starting material
DERIVATIVES
OF
CARBOXYLIC ACIDS
Structure and nomenclature of the
carboxylic acid derivatives
1) EsterS
2)Acid Chlorides
3) Acid Anhydrides
4) Amides
NUCLEOPHILIC ACYL SUBSTITUTION REACTIONS

O Nu:- L:-
+ O
R C L H Nu: +
R C Nu H L
L = Cl, OH,OR, NR2, H-Nu:
OCOR
H-OH, H-OR,
H-NR2, H-OCOR
General mechanism
Nuetral nucleophile

-ve nucleophile

Acid catalyzed
a) Nuc Acyl Subst. reaction of ACID CHLORIDES
b) Nuc Acyl Subst. reaction of ACID ANHYDRIDES
C) Nuc Acyl Subst. reaction of CARBOXYLIC ACIDS
d) Nuc Acyl Subst. reaction of ESTERS
e) Nuc Acyl Subst. reaction of AMIDES
NUCLEOPHILIC ADDITION REACTIONS OF
CARBOXYLIC ACID DERIVATIVES

• Reduction with LiAlH4


-all acid derivatives can be reduced to 1 o
ROH except amide
- amides is reduced to amines

O
LiAlH4 H2O, H+
R C NR2
RCH2NR2
2) Reaction with Grignard Reagents
-esters and acid chloride react with grignard reagent to produce 3o
ROH
REACTION OF ACID DERIVATIVES INVOLVING
CARBANIONS

A) Malonic ester Synthesis – to prepare disubstituted acetic acids


O
C OEt
OEt = OCH2CH3
CH2
C OEt
O

H O R O
H C C H C C
H OH R OH
Mechanism:
How to prepare 2-isopropylpentanoic acid from malonic ester?
b) Claisen Condensation
– an ester is converted to β-keto ester

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