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Lecturer: Joel H. G. Tolentino, PhD JHGT Lecture Notes; DO NOT reproduce nor
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Chapter 14 • Functional group is the carboxyl group, -COOH, a

Carboxylic Acids and Derivatives combination of the carbonyl (-C=O) and hydroxyl
(-OH) groups
Structure, Nomenclature and Physical
Properties

Acidity of Carboxylic Acids

• Replacement of –OH in carboxyl group gives rise
Preparation of Carboxylic Acids
to different functional derivatives of carboxylic
acid
Chemical Reactions: Nucleophilic Acyl
Substitution (interconversion)
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• General formula of CA and D is: • Carboxylic Acid

acyl group

• CA and D are also called acyl compounds

• The common derivatives… (see handout)

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• Acid Halide • Ester

• Acid Anhydride • Amide

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• Carboxylic acids (CAs) have higher BP and MP • Amides have quite high BPs  capable of strong
than alcohols of comparable MW intermolecular H-bonding

H-bonding in amides
CAs can form
dimeric structures

• Acid chlorides, acid anhydrides and esters  BP

are comparable to those of aldehydes and ketones
of same MW  BP lower than alcohols and CAs

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Arrange the following compounds in order of • Acidity is due to:

increasing BP. 1. H in –COOH being bonded to electronegative O

1. diethylether, butanedioic acid, butanal and

1-butanol - + JHGT Lecture Notes; DO NOT reproduce nor
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2. propanamide, butanoyl chloride, butanamide

and propanoyl chloride 2. stability of the conjugate base upon
deprotonation

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• Acid strength  any factor that stabilizes the

carboxylate anion can increase acidity…

Electron-withdrawing groups (W)  increases acidity  stabilizes

the negative charge through dispersal of the charge

W = -F, -Cl, -Br, -NO2, -CHO

Electron-donating groups (D)  intensifies the negative charge 

destabilizes the anion  decreases acidity

D = -R, -OH, -OR, -NH2, -NHR

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1. Oxidative Methods (Review!)

some alkenes to aldehydes to CA

some alkynes to CA

alkyl benzene to benzoic acid

1 alcohols to aldehydes to CA

 aldehydes to CA

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2. Carboxylation of Grignard Reagent

3. Hydrolysis of Nitriles (-CN)

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End of Chapter 14

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