11.12: 13.12 Additional Exercises
- Page ID
- 183001
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)Physical Properties of Alcohols
13-1 Identify which compound is more acidic. Explain your reasoning for each choice.
13-2 Identify which is the most acidic proton in the following compounds. Explain your reasoning for each choice.
13-3 Draw all possible resonance forms of the conjugate base of phenol.
13-4 List the following compounds in order from most to least acidic.
13-5 Predict which compound of each pair is more soluble in water and explain your reasoning.
- butan-1-ol or pentan-1-ol
- phenol or cyclohexanol
- octan-1,3-diol or octan-1-ol
- 1-chlorohexane or hexan-1-ol
13-6 Predict which compound has the higher boiling point and explain your reasoning.
- water or ethanol
- butan-1-ol or octan-1-ol
- hexan-2-ol or hexan-2-one
Synthesis of Alcohols
13-7 Show a possible way to synthesize the following alcohols.
13-8 Give the product of each reaction.
13-9 Give the product of each reaction.
13-10 Give the product of each reaction.
13-11 Give the product of each reaction.
Organometallic Reagents for Alcohol Synthesis
13-12 Draw the products of the following reactions.
13-13 Draw the products of the following reactions.
13-14 What is the final product of the following reaction.
13-15 Draw the mechanism for question 13-14.
13-16 Identify the product of the following reaction and explain why that is the correct answer.
Addition of Organometallic Reagents to Carbonyl Compounds
13-17 Give the product(s) of the following reactions. Include stereochemistry when necessary.
13-18 Show a possible carbonyl compound that was used to make the following alcohols through a Grignard reaction.
13-19 For the following compounds, identify the Grignard reagent used and the initial methyl ester compound.
13-20 Give the products of the following reactions.
Reduction of the Carbonyl Group
13-21 Identify whether the initial compound is undergoing oxidation or reduction.
13-22 Give the product of each reaction.
13-23 Give the product of each reaction (same starting molecule), making sure to specify where each proton ends up in the final product.
13-24 Give the mechanism for the following hydride reduction reaction.
13-25 Draw the structures for A and B.
Thiols (Mercaptans)
13-26 Name the following compounds following IUPAC nomenclature.
13-27 Identify the product of the following reaction. Include stereochemistry if appropriate.
13-28 Identify the product of the following reaction.