Carboxylic acid and carboxylic acid derivatives Carboxylic acid and carboxylic acid derivatives Dr. Nabila Al Jaber

Carboxylic acid R-COOH Ar-COOH Aliphatic (carboxylic cid) aromatic (benzoic acid) 1) replace ane by -ic acid Nomenclature : CommonIUPACFormula No. C Formic acid Acetic acid Prpionic acid Butyric acid valeric acid Salicylic acid Benzoic acid Methanoic acid Ethanoic acid Prpanoic acid Butanoic acid Pentanoic acid 2-hydroxy ben. a HCOOH CH 3 COOH CH 3 CH 2 COOH CH 3 (CH 2 ) 2 COOH CH 3 (CH 2 ) 3 COOH 12345

2) Longest continuous chain CH 3 CH 2 CHCH 2 CH 2 COOH 4-Methyl hexanoic acid CH 3      C-C-C-C-C-COOH CH 3 CH 2 CHCH 2 CH 2 COOH γ-Methyl hexenoic acid CH 3

commmone:  -  - Dimethyl butyric acid IUPAC: 2,3-Dimethyl butanoic a CH 3 -CHBr-CHCl-CO 2 H 3-Bromo-2-chlorobutnoic acid

3) In cyclic ring cycloalkane carb. a'

5) Aromatic acid by common name

Physical properties 1] They form hydrogen 2] comp. 1-7 soli in H 2 O. 3] mor than 7 carbon less soli. (bec. R increased) 4] Aromatic acids insoluble. In H 2 O 5] BP. Acid > Alcohol

Deac. gps inc. acidity Acti gps dec. acidity

HCOOH > CH 3 COOH > CH 3 CH 2 COOH > CH 3 CH 2 CH 2 COOH More acidity Substitution with halogen : CH 3 CH 2 COOH < CH 2 Cl-CH 2 COOH (more acidic) CH 3 CH 2 COOH < CH 2 ClCOOH < CHCl 2 COOH < CCl 3 COOH More acidity

Preparation of carboxylic acid 1] Oxidation a) 1  alcohols & Aldehydes

Preparation of carboxylic acid

b) of alkyl benzene

2)Hydrolysis of nitriles

3] Carbonation of Grignard reagent:

Preparation of carboxylic acid Hofmann Reaction Hofmann Reaction Collb’s Reaction Collb’s Reaction

Reactions of acids 1)Salt formation: it react with strong base & we can use CaOH, NaOH or KOH

reaction with weak base Sodium bicarb. Can be used to distinguish between carboxylic acid and phenols Reactions of acids

2) Formation of Easter: 3) Formation of amide: Reactions of acids

4) Formation of acid anhydride: 5) Formation of acid chloride: Reactions of acids

Addition anti marco.

Nomenclature of carboxylic acid derivatives When Oxygen of Carboxylic acid is replaced with Nu Carb. a' deriv

1] Salt:

2] Acid chloride

3] Ester: The alkyl gp. Named 1st then the name of parent acid with ending – ate in place of -ic acid

4]Amides: -oic acid or -ice a' by – amide.f 1 or 2 subst. on nitrogen we say N-subs. or N,N-disubs. (sub. Name 1st )

4] Acid anhydride: replacing -acid with anhydride

R-CO-Cl > R-(CO) 2 O-R > RCO 2 R > RCO 2 H > RCONH 2 Acid chloride Acid anhydride Ester Acid Amide Order of reaction: Benzoic acid anhydride

AMIDESAMIDES

ESTER S

ANHYDRIDESANHYDRIDES

Overview Reaction

Reactions of acid derivatives a) Acid chlorides: Reduction:

B] Acid anhydride: Reduction:

C] Esters: Reduction:

d] Amide: Reduction: Dehydration: Hoffman degradation: