Nucleophilic Substitution

Nucleophilic substitution

1. nucleophilic addition to acid derivative

2. pi donation

Result: nucleophile replaces another group or atom (the leaving group) in a molecule

pi donation

reverse of nucleophilic addition mechanistic step

acid derivatives

Compounds containing functional groups that can be converted to carboxylic acids by acidic or basic hydrolysis

acid derivative reactivity

Mechanism for Acid Chloride to Ester

acid chloride to aldehyde

1. LiAl(OR)3H

2. H2O

acid chloride to alcohol

1) LAH

2) H2O

acid derivatives to tertiary alcohol

carboxylic acid to acid chloride

SOCl2

carboxylic acid to ester

1. SOCl2

2. Alcohol

acid chloride to amide

NH3

Acid Chloride to Anhydride

R'COOH, R'COO-

Alcohol to sulfonate ester

sulfonyl chloride

Hydrolysis of amides

NaOH

Hydrolysis of esters

NaOH

basic hydrolysis of nitriles

NaOH

Claisen Condensation

enolate ion of one ester acts as nucleophile attacking another ester