20.13: Additional Exercises
- Page ID
- 183133
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)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.