Organic Chemistry II - Reagents

Hg(OAC)_{2 ,} NaBH₄

Alkoxymercuration / demercuration is a two-step process to convert alkenes to alcohols or esters.

Cis diene, dienophile

Diels-Alder → 4+2 ring formation

Ether, excess HBr or HI, other halides

cleavage of ether into two alkyl halides or phenol +alkyl halide if benzene ring is present

Carboxylic acid, alcohol, strong acid

Fischer esterification → ester

Double OEt on double ester, alkyl halide,NaOEt, H₃O⁺, heat

Malonic ester synthesis → substituted carboxylic acid

Single OEt on double ester, alkyl halide, NaOEt, H₃O⁺, heat

Acetoacetic ester synthesis → substituted ketone

Ketone or Carbonyl (C=O), Ph₃P=C_xH_x

Wittig Rxn → changes ketone/carbonyl into alkene

Aromatic ring, Alkyl halide, lewis acid catalyst (AlCl₃)

Friedel Craft Alkyl/Acyl → adds alkyl group (C) or acyl group(C=O) to aromatic rings

Alcohol + Alkyl Halide, strong Base

Williamson Ether Syn → alcohol is deprotonated by base, O^-then attacks alkyl halide to form an ether

Ketone +Ketone, -OH

Michael addition → 1,5 Dicarbonyl → cylic Aldol reaction → ring + 2 carbonyl

MgBr plus carbonyl, H3O+