有机合成必看(官能团转换).docVIP

Reactions of Alcohols - I (Carey, Chap. 4 +) Reaction Product Notes Prep. of alkoxides;conjugate bases of ?? pKa 16-18 acids SN1 subst. (2o 3o);carbocation intermediaterearrangement possiblerel. rates: HBr HCl; 3o 2o SN2 subst.;no rearrangement rel. rates: 1o 2o SN2 subst.;no rearrangement rel. rates: 1o 2o Chap. 8sulfonate estersgood leaving groups,(like halide) Chap. 5E1 elimination;carbocation intermediaterearrangement possible Chap. 10allylic carbocationresonance stabilized Reactions of Alkenes (Carey, Chap. 6 +) Reaction Product Notes carbocation intermediaterearrangement possible cyclic halonium ion, no rearrangementBr2 diagnostic for C=C cyclic halonium ion, no rearrangement carbocation intermediaterearrangement possible synchronous addn ofB H,no rearrangement ? Chap. 15concerted addition, 6 e- cyclic transition state epoxidation;concerted addition alkene cleavage;useful for structureelucidation alkene cleavage;useful for structureelucidation ? Chap. 9addition, followed bydouble E2 eliminationof vicinal dihalide;prep. of alkynes Chap. 10allylic free radical;resonance-stabilizedNBS = N-bromosuccinimide Chap. 10allylic carbocation;resonance-stabilized1,2-adduct major with??kinetic control1,4-adduct major with??thermodyn. control Chap. 10allylic carbocation;resonance-stabilized1,2-adduct major with??kinetic control1,4-adduct major with??thermodyn. control Reactions of Alkyl Halides (Carey, Chap. 8 +) Reaction Product Notes SN2 with strong Nu:- polar aprotic solvent.SN1 with weak Nu: protic solvent.Rearrangement possiblewhen SN1. also Chap. 5E2 elimination;requires anti-parallelconformation;no rearrangement ? Chap. 9double E2 eliminationof vicinal dihalide;prep. of alkynes ? Chap. 9double E2 eliminationof geminal dihalide;prep. of alkynes Chap. 10E1 or E2 elimination Re