540 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION (f) Water attacks the carbonyl group of benzoyl chloride to form the tetrahedral intermediate CsH CCI H,O CH-CCI tetrahedral oride Dissociation of the tetrahedral intermediate occurs by loss of chloride and the proton on C6HSCOH HCI Benzoic acid 20.5 One equivalent of benzoyl chloride reacts rapidly with water to yield benzoic acid C6HSCCI H,O C6HSCOH HCI Hydrogen chloride The benzoic acid produced in this step reacts with the remaining benzoyl chloride to give benzoic anhydride C6HSCCI CBH_ COH CBH_COCC H5 HCl enz Benzoic acid Benzoic anhydride Hydrogen 20.6 Acetic anhydride serves as a source of acetyl cation CH, CO-CCH3 CCH O≡CCH Acetyl catio 20.7(b) Acyl transfer from an acid anhydride to ammonia yields an amide. 00 CH, COCCH3 2NH, CHaCNH,+ CH3 CO NH4 Acetic anhydride ammonia etamide Ammonium acetate The organic products are acetamide and ammonium acetate Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website( f) Water attacks the carbonyl group of benzoyl chloride to form the tetrahedral intermediate. Dissociation of the tetrahedral intermediate occurs by loss of chloride and the proton on oxygen. 20.5 One equivalent of benzoyl chloride reacts rapidly with water to yield benzoic acid. The benzoic acid produced in this step reacts with the remaining benzoyl chloride to give benzoic anhydride. 20.6 Acetic anhydride serves as a source of acetyl cation. 20.7 (b) Acyl transfer from an acid anhydride to ammonia yields an amide. The organic products are acetamide and ammonium acetate. Acetic anhydride CH3COCCH3 O O 2NH3 Ammonia CH3CNH2 O Acetamide CH3CO NH4 O Ammonium acetate Acetyl cation CH3CO O CCH3 O O CCH3 O CCH3 HCl Hydrogen chloride C6H5COCC6H5 O O Benzoic anhydride C6H5CCl O Benzoyl chloride C6H5COH O Benzoic acid H2O Water C6H5CCl O Benzoyl chloride HCl Hydrogen chloride C6H5COH O Benzoic acid HCl Hydrogen chloride C6H5COH O Tetrahedral Benzoic acid intermediate C6H5C Cl O H OH C6H5CCl O Benzoyl chloride H2O Water Tetrahedral intermediate C6H5CCl OH OH 540 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website