538 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION (d) Acyl transfer from benzoyl chloride to the nitrogen of methylamine yields the amide N-methyl C6HsCCI 2CH,NH C6HSCNHCH3 CHaNH3 CI Benzoyl Methy lamine N-Methy benzamide chloride (e) In analogy with part(d), an amide is formed. In this case the product has two methyl groups CI t 2(CH)2NH H3)2+(CH3)2NH2 (f) Acyl chlorides undergo hydrolysis on reaction with water. The product is a carboxylic acid CsH +H2O—CH5COH+HCl Hyd chloride 20.4(b) Nucleophilic addition of benzoic acid to benzoyl chloride gives the tetrahedral intermediate own C6HsCCI CH COH C6H-COCC6H5 Benzoic acid Dissociation of the tetrahedral intermediate occurs by loss of chloride and of the proton on the oxygen. C6H-COCC6H5 C6H COCC6H5 HCI Tetrahedral intermediate Benzoic anhydrid chloride (c) Ethanol is the nucleophile that adds to the carbonyl group of benzoyl chloride to form the tetrahedral intermediate C6HSCCI CH, CH,OH C6H, CH3 Ethanol Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website538 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION (d) Acyl transfer from benzoyl chloride to the nitrogen of methylamine yields the amide N-methyl￾benzamide. (e) In analogy with part (d), an amide is formed. In this case the product has two methyl groups on nitrogen. ( f) Acyl chlorides undergo hydrolysis on reaction with water. The product is a carboxylic acid. 20.4 (b) Nucleophilic addition of benzoic acid to benzoyl chloride gives the tetrahedral intermediate shown. Dissociation of the tetrahedral intermediate occurs by loss of chloride and of the proton on the oxygen. (c) Ethanol is the nucleophile that adds to the carbonyl group of benzoyl chloride to form the tetrahedral intermediate. C6H5CCl O Benzoyl chloride CH3CH2OH Ethanol Tetrahedral intermediate C6H5COCH2CH3 OH Cl C6H5COCC6H5 O O Benzoic anhydride HCl Hydrogen chloride Tetrahedral intermediate C6H5COCC6H5 O H Cl O C6H5CCl O Benzoyl chloride C6H5COH O Benzoic acid C6H5COCC6H5 HO Cl O Tetrahedral intermediate C6H5CCl O Benzoyl chloride H2O Water C6H5COH O Benzoic acid HCl Hydrogen chloride C6H5CCl O Benzoyl chloride 2(CH3)2NH Dimethylamine C6H5CN(CH3)2 O N,N-Dimethylbenzamide (CH3)2NH2 Cl C6H5CCl O Benzoyl chloride 2CH3NH2 Methylamine C6H5CNHCH3 O N-Methylbenzamide CH3NH3 Cl Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website