Carboxylic Acid Reactions

Carboxylic Acid Reactions - 3/amine with an acid anhydride...

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Carboxylic Acid Reactions Preparation of Carboxylic Acids 1) Oxidation of 1 o alcohols with a strong oxidizer (see Alcohol reactions sheet) 2) Oxidation of alkyl side chains on benzene rings (see Benzene reactions sheet) 3) Grignard plus CO 2 MgX CO 2 H + 2) O OH 2) Hydrolysis of a nitrile N H 2 O H + or OH - OH O ** To form a nitrile, react a 1 o alkyl halide with the CN - ion ** X CN - N Preparation of acyl halides (acid chorides and acid bromides) 1) React a carboxylic acid with SOCl 2 , PBr 3 , or PCl 3 O OH SOCl 2 Cl O O OH PX 3 O X Preparation of acid anhydrides 1) React an acyl halide with a carboxylic acid O OH + R O X O O O R 2) Dehydration (heating) of a carboxylic acid O OH + R O OH O O O R heat
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Preparation of Esters 1) Equilibrium reaction of a carboxylic acid and an alcohol (less desirable) O OH + R R' OH O O R R 2) Reaction of an alcohol with an acid anhydride or acyl halide (desirable) OH R O X + R O O R O X + R O OR' R'OH Preparation of Amides (i.e amine) 1) Less desirable -- Heating a carboxylic acid with NH 3 /amine (the N group must have at least one H on it) O OH + O NR 2 HNR 2 heat 2) More desirable -- Reaction of NH
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Unformatted text preview: 3 /amine with an acid anhydride or acyl halide (the amine must have an H) R' O X HNR 2 + R' O NR 2 R' O O O R' HNR 2 + R' O NR 2 Reactions of Carboxylic Acids 1) Salt formation – reaction of a carboxylic acid with an alkali metal hydroxide (NaOH, LiOH, KOH) O OH MOH O O M Reactions of Esters 1) Hydrolysis R O O R' H 2 O H + R O OH + R'OH 2) Transesterification R O O R' R"OH R O O R" + H + R'OH 3) Ammonoylsis R O O R' NH 3 heat R O NH 2 + R'OH 4) Saponification R O O R' NaOH H 2 O, heat R O O Na + + R'OH 5) Reduction – produces a primary alcohol R O O R' R OH + R'OH LiAlH 4 , ether H + 2) 1 o alcohol 6) Grignard reaction – produces a tertiary alcohol R O O R' R R" R" OH 2 R"MgX ether 2) H + Reactions of Amides 1) Hydrolysis R O NH 2 H 2 O H + R O OH + , heat NH 3 2) Alcoholysis R O NH 2 R"OH R O O R" + H + , heat NH 3 3) Reduction – use LiAlH 4 to produce an amine R O NH 2 R NH 2 LiAlH 4 , ether H + 2)...
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Carboxylic Acid Reactions - 3/amine with an acid anhydride...

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