542 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION A second molecule of dimethylamine abstracts a proton from the tetrahedral intermediate L)NH N(CH3)2 CO H,N(CH3)2 Tetrahedral mediate sec Product of reaction imethy lamin (d) Hydroxide acts as a nucleophile to form the tetrahedral intermediate and as a base to facilitate Formation of tetrahedral intermediate: +m一 thalia anhydride OH HO O Dissociation of tetrahedral intermediate oH COH +h. In base, the remaining carboxylic acid group is deprotonated. Co-H OH CO 十 CO Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE WebsiteA second molecule of dimethylamine abstracts a proton from the tetrahedral intermediate. (d) Hydroxide acts as a nucleophile to form the tetrahedral intermediate and as a base to facilitate its dissociation. Formation of tetrahedral intermediate: Dissociation of tetrahedral intermediate: In base, the remaining carboxylic acid group is deprotonated. CO CO O O H2O H CO CO O O OH O OH O O H COH CO O O HO H2O Tetrahedral intermediate O HO OH O O O OH O H2O OH Phthalic anhydride O O O O O OH OH O Tetrahedral intermediate second Product of reaction molecule of dimethylamine O N(CH3)2 O O H (CH3)2NH CN(CH3)2 CO O O H2N(CH3)2 542 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website