ABSTRACT
Chapter 18, Section 18.1) • fundamentals of acyl substitution and the structure of a tetra-
hedral intermediate (Chapter 16, Section 16.8) • acid-base reactions of the carbonyl group and formation of oxo-
carbenium ions (Chapter 18, Sections 18.1 and 18.5) • how to identify a good leaving group (Chapter 11, Sections
11.1 and 11.2) • how to identify relative nucleophilic strength (Chapter 11,
Section 11.2; Chapter 18, Sections 18.3-18.7) • characteristics and reactivity of Grignard reagents, and organo-
lithium reagents (Chapter 15, Sections 15.1 and 15.5) • characteristics and reactivity of organocuprates (Chapter 15,
Section 15.6) • nucleophilic acyl addition of organometallic reagents to carbo-
nyl compounds (Chapter 18, Section 18.4) • acid-catalyzed nucleophilic acyl addition of weak nucleophiles
to carbonyl compounds (Chapter 18, Sections 18.5 and 18.6) • the mechanism of acetal and ketal formation (Chapter 18,
Section 18.6) • oxidation reactions of peroxyacids (Chapter 10, Section 10.5;
Chapter 17, Section 17.3) • reagents for the conversion of alcohols to alkyl halides (Chapter
11, Section 11.7)
This chapter will discuss methods for the preparation of esters, acid chlorides, anhydrides, and amides from carboxylic acids, based on acyl substitution reactions. Acyl substitution reactions of carboxylic acid derivatives will include hydrolysis, interconversion of one acid derivative into another, and reactions with strong nucleophiles such as organometallic reagents. In addition, the chemistry of dicarboxylic acid derivatives will be discussed, as well as cyclic esters, amides, and anhydrides. Sulfonic acid derivatives will be introduced as well as sulfate esters and phosphate esters. Finally, nitriles will be shown to be acid derivatives by virtue of their reactivity.
