Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH...

Carboxylic Acids

Introduction

The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon.

Carboxyl group is usually written -COOH .

Aliphatic acids have an alkyl group bonded to -COOH.

Aromatic acids have an aryl group.

Fatty acids are long-chain aliphatic acids.>=

Common Names

Many aliphatic acids have historical names.

Positions of substituents on the chain are labeled with Greek letters.

CH3CH2CHC

-chlorobutyric acid

CH3CH2CH2CHCH2COOH

-phenylcaproic acid

IUPAC Names

Remove -e from alkane (or alkene) name, add -oic acid.

The carbon of the carboxyl group is #1.

CH3CH2CHC

2-chlorobutanoic acid

trans-3-phenyl-2-propenoic acid (cinnamic acid)

Naming Cyclic Acids

Cycloalkanes bonded to -COOH are named as cycloalkanecarboxylic acids.

Aromatic acids are named as benzoic acids.

CH(CH3)2

2-isopropylcyclopentanecarboxylic acid

o-hydroxybenzoic acid(salicylic acid)

Dicarboxylic Acids

Aliphatic diacids are usually called by their common names (to be memorized).

For IUPAC name, number the chain from the end closest to a substituent.

Two carboxyl groups on a benzene ring indicate a phthalic acid.

HOOCCH2CHCH2CH2COOH

3-bromohexanedioic acid -bromoadipic acid =>

Structure of Carboxyl

Carbon is sp2 hybridized.

Bond angles are close to 120.

O-H eclipsed with C=O, to get overlap of orbital with orbital of lone pair on oxygen.

Boiling Points

Higher boiling points than similar alcohols, due to dimer formation.

Acetic acid, b.p. 118C =>

Melting Points

Aliphatic acids with more than 8 carbons are solids at room temperature.Double bonds (especially cis) lower the melting point. Note these 18-C acids:

Stearic acid (saturated): 72COleic acid (one cis double bond): 16CLinoleic acid (two cis double bonds): -5C>=

Solubility

Water solubility decreases with the length of the carbon chain.

Up to 4 carbons, acid is miscible in water.

More soluble in alcohol.

Also soluble in relatively nonpolar solvents like chloroform because it dissolves as a dimer. >=

Acidity

Resonance Stabilization

Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH...

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