9.19: Additional Exercises
- Page ID
- 122586
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)Addition of Hydrogen Halides to Alkenes
9-1 Give the IUPAC name for the product of the following reaction.
9-2 Draw the reaction mechanism of the previous problem (9-1).
9-3 Identify the product of the following reactions.
9-4 Identify the products of the following reactions.
Addition of Water: Hydration of Alkenes
9-5 Identify the product of the following reactions.
9-6 Identify the product of the following reaction.
9-7 Propose a plausible route of synthesis for the following product starting with 1-butanol.
9-8 Which of the following alkenes can be used to obtain 3,4-dimethylpentan-2-ol through a hydration reaction using dilute acid?
a) (2Z)-3,4-dimethylpent-2-ene
b) 3,4-dimethylpent-1-ene
c) 2,3,4-trimethylpent-2-ene
d) 2,4-dimethyl-3-methylidenepentane
Hydration by Oxymercuration-Demercuration
9-9 Explain why hydration of an alkene by Oxymercuration-Demercuration gives the Markovnikov product.
9-10 Identify the products of the following reactions.
9-11 Identify the product of the following reaction.
9-12 Propose a possible route of synthesis for the following ether starting with 2-ethylbutan-1-ol.
9-13 Give the IUPAC name of the product of the following reaction.
a) 2-methylpropan-2-ol
b) 2,2-dimethylbutane
c) 2-methoxy-2-methylpropane
d) 1,1-dimethylcyclopropane
Hydroboration of Alkenes
9-14 Identify the products of the following reactions.
9-15 Identify the products of the following reactions.
9-16 Give the IUPAC name for the product of the following reaction.
Addition of Halogens to Alkenes
9-17 Identify the products of the following reactions.
9-18 Identify the product of the following reaction.
9-19 What is the product of the following reaction?
a) (2Z)-2-bromo-3-methylpent-2-ene
b) 2-bromo-3-methylpentane
c) 2,3-dibromo-3-methylpentane
d) (2E)-4-bromo-3-methylpent-2-ene
9-20 What reagents can be used in each step to obtain the following products?
9-21 Explain why you do not obtain a mixture of cis- and trans-brominated products when you react Br2/CCl4 with cyclopentene.
Formation of Halohydrins
9-22 Identify the product of the following reaction, making sure to include stereochemistry.
9-23 Draw the mechanism of the reaction in the previous problem (9-22).
9-24 Give the IUPAC name for the product of the following reaction.
9-25 Identify the product of the following reaction.
Catalytic Hydrogenation of Alkenes
9-26 Identify the products of the following reactions.
9-27 Suggest a possible route of synthesis, that includes a catalytic hydrogenation step, to obtain the following product.
9-28 Identify the product of the following reaction.
9-29 Identify the product of the following reaction, making sure to include stereochemistry.
Addition of Carbenes to Alkenes
9-30 Identify the product of the following reaction.
9-31 Identify the product(s) of the following reaction.
9-32 Identify the product of the reaction when (2E)-3-methylhex-2-ene reacts with the carbene product from the previous problem (9-31), then reacts with Br2 and hv.
9-33 Propose a possible route of synthesis for the following reaction.
9-34 Identify the product of the following reaction.
Epoxidation of Alkenes and Acid-Catalyzed Opening of Epoxides
9-35 Identify the product of the following reaction.
9-36 Identify the product of the following reactions, specifying stereochemistry where appropriate.
9-37 Identify the products of the following reaction, including stereochemistry.
9-38 What is the product of the following reaction?
a) benzoic acid
b) 1-cyclohexylethan-1-ol
c) 1-cyclohexylethan-1-one
d) cyclohexanol
9-39 What is the product of the following reaction?
a) 4-chlorobutane-1,3-diol
b) 3-chlorobutan-1-ol
c) 2-chlorobutane-1,4-diol
d) 2,4-dichlorobutan-1-ol
9-40 Draw the arrows for the following epoxidation reaction to show the movement of electrons.
Syn Dihydroxylation of Alkenes
9-41 Identify the product of the following reaction, including stereochemistry.
9-42 Give the IUPAC name for the product(s) of the following reaction. Include stereochemistry.
9-43 Identify the product of the following reaction.
9-44 Suggest a possible route of synthesis for the following compound starting with cyclopentanol.
Oxidative Cleavage of Alkenes
9-45 Identify the products of the following reactions.
9-46 Identify the products of the following reactions.
9-47 Identify the product of the following reaction.
Polymerization of Alkenes
9-48 Identify the alkene monomer that composes the following polymer.
9-49 Draw the mechanism for the acid catalyzed formation of the polymer in the previous problem (9-48).
9-50 Draw the resulting polymer of the following reaction. Draw the chain four monomers in length.