ABSTRACT
Section 5.7; Chapter 6, Section 6.4.4) • mechanisms (Chapter 7, Section 7.8) • carbocations (Chapter 10, Section 10.2; Chapter 11, Section 11.4) • the concept of Lewis acids and Lewis bases (Chapter 6, Section 6.5) • the concept of a nucleophile (Chapter 6, Section 6.7; Chapter 11,
Sections 11.2 and 11.3) • the concept of a leaving group (Chapter 11, Section 11.2.4) • the SN2 transition state and the fundamental mechanistic details
of the SN2 reaction (Chapter 11, Sections 11.1-11.3)
This chapter will revisit the IUPAC nomenclature system for aldehydes, ketones, and carboxylic acids, as well as introduce nomenclature for the four main acid derivatives: acid chlorides, anhydrides, esters, and amides. The chapter will show the similarity of a carbonyl and an alkene in that both react with a Brønsted-Lowry acid or a Lewis acid. The reaction of a carbonyl compound with an acid will generate a resonance stabilized oxocarbenium ion. Ketones and aldehydes react with nucleophiles by what is known as acyl addition to give an alkoxide product, which is converted to an alcohol in a second chemical step. Acid derivatives differ from aldehydes or ketones in that a leaving group is attached to the carbonyl carbon. Acid derivatives react with nucleophiles by what is known as acyl substitution, via a tetrahedral intermediate.
