Ch. 14 – Complex Reaction Mechanisms- Top ten

___ reaction mechanisms can be combined into more ___ mechanisms

simple; complex

The ___ involves the treatment of an aldehyde or ketone with hydrazine and hydroxide at elevated temperatures to afford a methylene (alkane)

Wolff-Kishner Reduction

The ___ intermediate of the Wolff-Kishner is isomerized by the base to a diazene; deprotonation of the diazene eliminates N2 and forms a carbanion

hydrazone

___ protonation of the carbanion ends the Wolff-Kishner

Irreversible

The ___ forms a new cyclohexenone ring from ketone (often β-diketone) and an α,β-unsaturated ketone

Robinson Annulation

The Robinson Annulation involves an initial ___ followed, after proton transfers, by an intramolecular aldol condensation

Michael addition

___ can be formed from aldehydes and ketones by treatment with an alcohol in the presence of acid

Acetals

___ involves the initial addition of the alcohol to the carbonyl to form a hemiacetal intermediate; the hemiacetal is converted to an acetal by __ with the alcohol

Acetal formation; SN1 displacement

Treatment of a primary amine with nitrous acid (HONO) results in the formation of a ___

diazonium ion

____ are often unstable due to β-elimination of N2; aryl diazonium ions are stable at 0 ∘C and useful synthetic intermediates

Alkyl diazonium ions