# 9.19: Additional Exercises

$$\newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} }$$

$$\newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}}$$

$$\newcommand{\id}{\mathrm{id}}$$ $$\newcommand{\Span}{\mathrm{span}}$$

( \newcommand{\kernel}{\mathrm{null}\,}\) $$\newcommand{\range}{\mathrm{range}\,}$$

$$\newcommand{\RealPart}{\mathrm{Re}}$$ $$\newcommand{\ImaginaryPart}{\mathrm{Im}}$$

$$\newcommand{\Argument}{\mathrm{Arg}}$$ $$\newcommand{\norm}[1]{\| #1 \|}$$

$$\newcommand{\inner}[2]{\langle #1, #2 \rangle}$$

$$\newcommand{\Span}{\mathrm{span}}$$

$$\newcommand{\id}{\mathrm{id}}$$

$$\newcommand{\Span}{\mathrm{span}}$$

$$\newcommand{\kernel}{\mathrm{null}\,}$$

$$\newcommand{\range}{\mathrm{range}\,}$$

$$\newcommand{\RealPart}{\mathrm{Re}}$$

$$\newcommand{\ImaginaryPart}{\mathrm{Im}}$$

$$\newcommand{\Argument}{\mathrm{Arg}}$$

$$\newcommand{\norm}[1]{\| #1 \|}$$

$$\newcommand{\inner}[2]{\langle #1, #2 \rangle}$$

$$\newcommand{\Span}{\mathrm{span}}$$ $$\newcommand{\AA}{\unicode[.8,0]{x212B}}$$

$$\newcommand{\vectorA}[1]{\vec{#1}} % arrow$$

$$\newcommand{\vectorAt}[1]{\vec{\text{#1}}} % arrow$$

$$\newcommand{\vectorB}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} }$$

$$\newcommand{\vectorC}[1]{\textbf{#1}}$$

$$\newcommand{\vectorD}[1]{\overrightarrow{#1}}$$

$$\newcommand{\vectorDt}[1]{\overrightarrow{\text{#1}}}$$

$$\newcommand{\vectE}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{\mathbf {#1}}}}$$

$$\newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} }$$

$$\newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}}$$

## 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.

9.19: Additional Exercises is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.