有机反应机理的书写艺术课后答案-第二章-The-Art-of-writing-reasonable-.pdf

Answers To Chapter 2 In-Chapter Problems. 2.1. LDA is a strong base. Two E2 eliminations give an alkyne, which is deprotonated by the excess LDA to give an alkynyl anion. This species then reacts with MeI by an SN2 process. Cl OMe – H OMe N(i-Pr ) 2 H H H OMe H OMe – H OMe – (i-Pr )N N(i-Pr ) 2 2 Me I MeO MeO Me 2.2(a). LDA deprotonates the C α to the ester, which adds to the aldehyde to give the aldol product after workup. O O O O O H C – H C 3 N(i-Pr ) 3 2 Et H3C O H H3C O CH3 CH3 O O H C 3 Et workup H3C O H product CH3 O– 2.2(b). BuLi deprotonates the C α to the nitrile, which adds to the ketone to give the aldol product after workup. O Et Et H O– Li B