20.13: Additional Exercises

Last updated
Save as PDF

Page ID: 183133

\( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\)

General Review

22-1 Suggest a carboxylic acid and an acid derivative that could be reacted together to form the following molecule.

22-2 For the following reaction, predict the product if:

only one equivalent of the Grignard reagent was used (and the product could be isolated)
if two equivalents were used (followed by an acid workup)

22-3 Provide the final products of the following reactions.

22-4 Predict the final product of the following reaction.

Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution

22-5 Predict the interconverted acid derivatives of the following reactions.

22-6 Predict the structure of the product and give its IUPAC nomenclature.

22-7 Choose the correct answer for the product of the following reaction.

Transesterification

22-8 Choose the correct IUPAC nomenclature of the product of the following reaction.

a) ethyl butanoate

b) propan-2-yl butanoate

c) dipropyl carbonate

d) propyl butanoate

22-9 Explain why transesterification can be done under acidic or basic conditions.

22-10 Give the products of the following transesterification reactions.

Hydrolysis of Carboxylic Acid Derivatives

22-11 Provide the correct structure of the product of the following hydrolysis reaction.

22-12 Provide the structure of all the products resulting from the hydrolysis of the following triglyceride.

22-13 Provide the structures and IUPAC nomenclature of the products.

Reduction of Acid Derivatives

22-14 Give the structure of the product of the following reaction.

22-15 Provide the structure of all the products (including leaving groups) formed in the following reaction.

22-16 Choose the correct answer that gives the products of a fully reduced 1,3-dimethyl-1,3-diazinan-2-one.

Reactions of Acid Derivatives with Organometallic Reagents

22-17 Predict the product of the following reaction.

22-18 Choose the correct IUPAC nomenclature of the product of the following reaction.

a) 6-amino-5-chlorohexan-2-one

b) 6-amino-5-chloro-2-methylhexan-2-ol

c) 6-amino-4-chloro-2-methylhexan-2-ol

d) 4-chloro-2-methylpiperidin-2-ol

22-19 Decide whether or not the following reaction is the best way to obtain the final product. If not, suggest a better route of synthesis.