ABSTRACT
Section 17.2; Chapter 21, Section 21.3.3) • keto-enol tautomerism (Chapter 10, Sections 10.6.3 and 10.6.4;
Chapter 18, Section 18.5) • the E2 reaction (Chapter 12, Sections 12.1 and 12.2) • the SN2 reaction with alkyl halides (Chapter 11, Sections
11.1-11.3) • differences in nucleophilic strength (Chapter 11, Section 11.3) • formation of Grignard reagents and organolithium reagents
(Chapter 15, Sections 15.1, 15.5) • that Grignard reagents and organolithium reagents are strong
bases (Chapter 15, Sections 15.3 and 15.5.2) • that amines react as acids in the presence of a strong base
(Chapter 15, Section 15.5.2; Chapter 6, Section 6.4.1) • acyl addition reactions of nucleophiles (Chapter 16, Section 16.3;
Chapter 18, Section 18.1) • acyl addition of organometallic reagents to aldehydes and
ketones (Chapter 18, Section 18.4) • reaction of alcohols and amines with aldehydes and ketones
(Chapter 18, Sections 18.6 and 18.7) • reactions that generate carboxylic acids (Chapter 17, Section 17.4;
Chapter 20, Section 20.2) • reactions that generate acid derivatives (Chapter 20, Sections
20.3-20.6) • acyl substitution reactions (Chapter 16, Section 16.8; Chapter
20, Section 20.1) • electron-releasing and -withdrawing substituents (Chapter 3,
Section 3.7; Chapter 21, Section 21.3) • how to identify a good leaving group (Chapter 11, Section 11.2) • how to convert alkoxide anions to the corresponding alcohol
via an acid-base workup (Chapter 5, Section 5.7; Chapter 6, Section 6.2; Chapter 18, Section 18.1)
• E and Z nomenclature (Chapter 9, Section 9.4)
• absolute configuration and stereogenic centers (Chapter 9, Sections 9.1 and 9.3)
• diastereomers (Chapter 9, Section 9.5) • decarboxylation (Chapter 12, Section 12.6)
This chapter will discuss carbanion-like reactions that utilize enolate anions. The acid-base reactions used to form enolate anions will be discussed. Formation of enolate anions from aldehyde, ketones, and esters will lead to substitution reactions, acyl addition reactions, and acyl substitution reactions. Several classical named reactions that arise from these three fundamental reactions of enolate anions are presented. In addition, phosphonium salts will be prepared from alkyl halides and converted to ylids, which react with aldehydes or ketones to form alkenes. These ylids are treated as phosphorus-stabilized carbanions in terms of their reactivity.
