John E. McMurry
ISBN #9781285842912
3rd Edition
1,528 Questions
Homework Questions
This section presents a comprehensive examination of carboxylic acid derivatives and their reactions, anchored on the mechanism of nucleophilic acyl substitution. Key naming rules and reactivity orders are discussed, along with detailed mechanisms for hydrolysis, alcoholysis, aminolysis, reduction, and Grignard reactions. Applications range from laboratory synthesis (including Fischer esterification and DCC-mediated amide formation) to the preparation of step-growth polymers and the activation processes in biological systems. Understanding these concepts is crucial to mastering both synthetic organic chemistry and the chemistry underlying biochemical pathways.
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CONCEPT
DEFINITION
Definition: The study of molecular reactivity via polar covalent bonds where differences in electronegativity create dipole moments, guiding acid–base behavior.
The study of molecular reactivity via polar covalent bonds where differences in electronegativity create dipole moments, guiding acid–base behavior. •
Give IUPAC names for the following substances: a. b. c. d. e. f. g. h. i.
Draw structures corresponding to the following names: (a) Phenyl benzoate (b) $N$ -Ethyl- $N$ -methylbutanamide (c) 2,4 -Dimethylpentanoyl chloride (d) Methyl 1-methylcyclohexanecarboxylate (e) Ethyl 3-oxopentanoate (f) Methyl $p$ -bromothiobenzoate (g) Formic propanoic anhydride (h) cis-2-Methylcyclopentanecarbonyl bromide
Show the mechanism of the following nucleophilic acyl substitution reaction, using curved arrows to indicate the electron flow in each step:
Rank the compounds in each of the following sets in order of their expected reactivity toward nucleophilic acyl substitution: a. b.
Predict the products of the following nucleophilic acyl substitution reactions: a. b. c. d.