21.12: Additional Exercises
- Page ID
- 183147
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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
23-1 For each of the following reactions, predict the product. Then identify which one gives the kinetic product and which one gives the thermodynamic product. Explain your reasoning.
23-2 Predict the final product of the following reaction.
23-3 Explain why we obtain the products shown below as a result of the base catalyzed α-halogenation reaction, instead of a single or double halogenated product.
23-4 Identify the starting molecule of the aldol addition-condensation reaction that resulted in the final product below.
23-5 The following reaction is an example of an intramolecular aldol addition-condensation reaction. Given the aldol product, identify the starting molecule and the condensation product.
23-6 Provide the final product of the following reaction (for now, ignore any stereochemistry).
23-7 Predict the final product of the following reaction.
Enols and Enolate Ions
23-8 Choose the correct IUPAC nomenclature of the product of the following reaction and provide its structure.
a) dibromo(4-methylphenyl)methanol
b) 4-methylbenzoic acid
c) 4-methylbenzoyl bromide
d) bromo(4-methylphenyl)methanol
23-9 Draw the mechanism for the following self-catalyzed halogenation reaction.
23-10 Predict the product of the following reaction.
Formation and Alkylation of Enamines
23-11 Choose the correct IUPAC nomenclature for the product of the following reaction.
a) (2Z)-N,N-diethylpent-2-en-3-amine
b) N,N-diethylpentan-3-amine
c) 3-(diethylamino)pentan-3-ol
d) Tetraethylhydrazine
23-12 Predict the major products of the following reactions.
23-13 Predict the product of the following reaction.
Alpha Halogenation of Ketones
23-14 Predict the product of the following reaction.
23-15 Draw the mechanism for the α-halogenation step of the ketone in problem 23-14.
23-16 Provide the structures of the products of the following reactions.
Alpha Bromination of Acids: The HVZ Reaction
23-17 Give the product of the following reaction.
23-18 Choose the correct IUPAC nomenclature of the product of the following reaction.
a) 1-chlorocyclohexane-1-carboxylic acid
b) 1-bromocyclohexane-1-carbonyl chloride
c) 1-chlorocyclohexane-1-carbonyl chloride
d) 1-hydroxycyclohexane-1-carbonyl bromide
23-19 Provide the structure and IUPAC nomenclature of the product of the following reaction.
The Aldol Condensation of Ketones and Aldehydes
23-20 Give the structure of the product of the following aldol condensation reaction.
23-21 Predict the structure of the product of the following reaction.
23-22 Provide the structure of the product of the following reaction.
Dehydration of Aldol Products
23-23 Choose the correct IUPAC nomenclature for the product of the following aldol condensation reaction.
a) 5-ethyl-4-methylheptan-3-one
b) 5-ethyl-4-methylhept-4-en-3-one
c) 5-ethyl-5-hydroxy-4-methylheptan-3-one
d) (5Z)-5-ethyl-4-methylhept-5-en-3-one
23-24 Provide the mechanism for the reaction to the answer for the previous question.
23-25 For the following compounds, draw a possible product of the condensation step.
Crossed Aldol Condensations
23-26 Provide the structure of the product of the following reaction.
23-27 Suggest the structures of the starting compounds that were reacted to create this final crossed aldol condensation product.
23-28 Provide the structures of all possible products of the following crossed aldol condensation reaction.
Aldol Cyclizations
23-29 Provide the IUPAC name for the product of the following intramolecular aldol condensation reaction.
23-30 Identify the starting material used to create the following products of aldol cyclization.
23-31 Starting with a single diketone molecule, propose a method of synthesis for the following compound that includes an aldol cyclization step.
Claisen Condensations
23-32 Predict the product of the following Claisen condensation reaction.
23-33 Predict the final product of the following reaction.
23-34 Provide the structure of the products of the following crossed Claisen condensation reactions.
Syntheses Using β-Dicarbonyl Compounds
23-35 Give the structure and IUPAC nomenclature of the product of the following reaction.
23-36 Choose the correct IUPAC nomenclature of the product of the following reaction.
a_ 2,2,4,4-tetramethylpentan-3-one
b) 2,2,4-trimethylpentan-3-one
c) 2,4,4-trimethylpent-1-en-3-one
d) 2,4,4-trimethyl-3-oxopentanoic acid
23-37 Suggest a way to make (5-methylhexyl)benzene from 3-hydroxy-5-methylhexanoic acid.
Conjugate Additions: The Michael Reaction
23-38 For the following pairs of compounds, identify the Michael acceptor and the Michael donor.
23-39 Predict the product of the following reaction chain.
23-40 Pick the answer that correctly names the product of the following Michael addition reaction.
a) 3-(ethylamino)butan-2-one
b) 2-(ethylamino)butan-2-ol
c) 4-(ethylamino)butan-2-one
d) 4-(methylamino)butan-2-one
The Robinson Annulation
23-41 Predict a possible product of the following reactions.
23-42 Given the following compound, predict the Michael acceptor and donor that initially reacted to allow for the aldol condensation to occur.
23-43 Given the following Robinson annulation product, identify the intermediate compound that results from the Michael addition and exists before the aldol condensation.