Mechanism Problems -

PROBLEM Assuming that halogens add to alkynes in the same manner as they add to alkenes, propose a
9-18 mechanism for and predict the product(s) of the reaction of phenylpropyne with $\mathrm{Br}_{2}$.
PROBLEM Assuming that strong acids add to alkynes in the same manner as they add to alkenes, propose a
9-19 mechanism for each of the following reactions.
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0299.jpg?height=113&width=638&top_left_y=1147&top_left_x=478)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0299.jpg?height=109&width=603&top_left_y=1149&top_left_x=1184)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0299.jpg?height=153&width=711&top_left_y=1271&top_left_x=482)


Mechanism Problems -

PROBLEM The mercury-catalyzed hydration of alkynes involves the formation of an organomercury enol
9-20 intermediate. Draw the electron-pushing mechanism to show how each of the following intermediates is formed.
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0299.jpg?height=145&width=898&top_left_y=1586&top_left_x=483)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0299.jpg?height=191&width=744&top_left_y=1753&top_left_x=479)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0299.jpg?height=214&width=822&top_left_y=1945&top_left_x=413)


Mechanism Problems -

PROBLEM The final step in the hydration of an alkyne under acidic conditions is the tautomerization of an enol
9-21 intermediate to give the corresponding ketone. The mechanism involves a protonation followed by a deprotonation. Show the mechanism for each of the following tautomerizations.
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0299.jpg?height=153&width=703&top_left_y=2317&top_left_x=475)
(b)
<img class="imgSvg" id = "m6sn3ndnikp6pxveg7" src="data:image/svg+xml;base64,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"/>
$\xrightarrow{\mathrm{H}_{3} \mathrm{O}^{+}}$
<img class="imgSvg" id = "m6sn3ndoosp4ey2fvmp" src="data:image/svg+xml;base64,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"/>
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0300.jpg?height=177&width=586&top_left_y=204&top_left_x=477)


Mechanism Problems -


Mechanism Problems -

PROBLEM Identify the mechanisms for the following reactions as polar, radical, or both.
9-23 (a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0300.jpg?height=150&width=771&top_left_y=711&top_left_x=479)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0300.jpg?height=148&width=774&top_left_y=880&top_left_x=475)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0300.jpg?height=122&width=734&top_left_y=1034&top_left_x=476)

PROBLEM Predict the product and provide the complete electron-pushing mechanism for the following two-
9-24 step synthetic processes.
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0300.jpg?height=135&width=471&top_left_y=1274&top_left_x=480)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0300.jpg?height=132&width=469&top_left_y=1273&top_left_x=1015)
(c)


Mechanism Problems -

$$
\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH} \xrightarrow{\text { 2. } \mathrm{PhCH}_{2} \mathrm{Br}}
$$


Mechanism Problems -

PROBLEM Reaction of acetone with $\mathrm{D}_{3} \mathrm{O}^{+}$yields hexadeuterioacetone. That is, all the hydrogens in acetone are
9-25 exchanged for deuterium. Review the mechanism of mercuric-ion-catalyzed alkyne hydration, and then propose a mechanism for this deuterium incorporation.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0300.jpg?height=147&width=548&top_left_y=1675&top_left_x=417)


Acetone -

Hexadeuterioacetone


Naming Alkynes -


Naming Alkynes -

PROBLEM Draw structures corresponding to the following names:
9-27 (a) 3,3-Dimethyl-4-octyne (b) 3-Ethyl-5-methyl-1,6,8-decatriyne
(c) 2,2,5,5-Tetramethyl-3-hexyne (d) 3,4-Dimethylcyclodecyne
(e) 3,5-Heptadien-1-yne
(f) 3-Chloro-4,4-dimethyl-1-nonen-6-yne (g) 3-sec-Butyl-1-heptyne
(h) 5-tert-Butyl-2-methyl-3-octyne


Naming Alkynes -

PROBLEM The following two hydrocarbons have been isolated from various plants in the sunflower family.
9-28 Name them according to IUPAC rules.
(a) $\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHC} \equiv \mathrm{CC} \equiv \mathrm{CCH}=\mathrm{CHCH}=\mathrm{CHCH}=\mathrm{CH}_{2}$ (all trans)
(b) $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CC} \equiv \mathrm{CC} \equiv \mathrm{CC} \equiv \mathrm{CC} \equiv \mathrm{CCH}=\mathrm{CH}_{2}$


Reactions of Alkynes -

PROBLEM Terminal alkynes react with $\mathrm{Br}_{2}$ and water to yield bromo ketones. For example:
9-29
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0301.jpg?height=199&width=719&top_left_y=627&top_left_x=410)


Reactions of Alkynes -

Propose a mechanism for the reaction. To what reaction of alkenes is the process analogous?
PROBLEM Predict the products of the following reactions:
9-30
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0301.jpg?height=202&width=681&top_left_y=967&top_left_x=413)


Reactions of Alkynes -

PROBLEM Predict the products from reaction of 1-hexyne with the following reagents:
9-31 (a) 1 equiv HBr (b) 1 equiv $\mathrm{Cl}_{2}$ (c) $\mathrm{H}_{2}$, Lindlar catalyst (d) $\mathrm{NaNH}_{2}$ in $\mathrm{NH}_{3}$, then $\mathrm{CH}_{3} \mathrm{Br}$
(e) $\mathrm{H}_{2} \mathrm{O}, \mathrm{H}_{2} \mathrm{SO}_{4}, \mathrm{HgSO}_{4}$ (f) 2 equiv HCl

PROBLEM Predict the products from reaction of 5-decyne with the following reagents:
9-32 (a) $\mathrm{H}_{2}$, Lindlar catalyst
(b) Li in $\mathrm{NH}_{3}$
(c) 1 equiv $\mathrm{Br}_{2}$
(d) $\mathrm{BH}_{3}$ in THF, then $\mathrm{H}_{2} \mathrm{O}_{2}, \mathrm{OH}^{-}$
(e) $\mathrm{H}_{2} \mathrm{O}, \mathrm{H}_{2} \mathrm{SO}_{4}, \mathrm{HgSO}_{4}$
(f) Excess $\mathrm{H}_{2}, \mathrm{Pd} / \mathrm{C}$ catalyst

PROBLEM Predict the products from reaction of 2-hexyne with the following reagents:
9-33 (a) 2 equiv $\mathrm{Br}_{2}$
(b) 1 equiv HBr
(c) Excess HBr
(d) Li in $\mathrm{NH}_{3}$
(e) $\mathrm{H}_{2} \mathrm{O}, \mathrm{H}_{2} \mathrm{SO}_{4}, \mathrm{HgSO}_{4}$


Reactions of Alkynes -

PROBLEM Propose structures for hydrocarbons that give the following products on oxidative cleavage by
9-34 $\mathrm{KMnO}_{4}$ or $\mathrm{O}_{3}$ :
(a) $\mathrm{CO}_{2}+\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{5} \mathrm{CO}_{2} \mathrm{H}$
(b)


Reactions of Alkynes -


Reactions of Alkynes -

PROBLEM Identify the reagents a-c in the following scheme: 9-35
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0301.jpg?height=172&width=1368&top_left_y=2055&top_left_x=411)


Reactions of Alkynes -

Organic Synthesis
PROBLEM How would you carry out the following multistep conversions? More than one step may be needed 9-36 in some instances.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0302.jpg?height=481&width=692&top_left_y=188&top_left_x=413)

PROBLEM How would you carry out the following reactions?
9-37 (a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0302.jpg?height=120&width=524&top_left_y=742&top_left_x=475)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0302.jpg?height=77&width=559&top_left_y=756&top_left_x=1073)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0302.jpg?height=152&width=681&top_left_y=870&top_left_x=478)
(d)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0302.jpg?height=209&width=687&top_left_y=1023&top_left_x=470)
(e)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0302.jpg?height=82&width=532&top_left_y=1032&top_left_x=1214)
(f)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0302.jpg?height=101&width=852&top_left_y=1245&top_left_x=474)

PROBLEM Each of the following syntheses requires more than one step. How would you carry them out?
9-38 (a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0302.jpg?height=83&width=619&top_left_y=1422&top_left_x=479)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0302.jpg?height=150&width=749&top_left_y=1519&top_left_x=479)


Reactions of Alkynes -

PROBLEM How would you carry out the following multistep transformation?
9-39
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0302.jpg?height=202&width=773&top_left_y=1753&top_left_x=416)


Reactions of Alkynes -

PROBLEM How would you carry out the following multistep conversions?


9-40 -


9-40 -

PROBLEM Synthesize the following compounds using 1-butyne as the only source of carbon, along with any
9-41 inorganic reagents you need. More than one step may be needed.
(a) 1,1,2,2-Tetrachlorobutane (b) 1,1-Dichloro-2-ethylcyclopropane


9-40 -

PROBLEM How would you synthesize the following compounds from acetylene and any alkyl halides with four 9-42 or fewer carbons? More than one step may be needed.
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CCH}_{2} \mathrm{CH}_{3}$
(c)
<img class="imgSvg" id = "m6sn3ndwpcedo3u5vcs" src="data:image/svg+xml;base64,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(d)
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(e) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CHO}$


9-40 -

PROBLEM How would you carry out the following reactions to introduce deuterium into organic molecules?
9-43 (a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0303.jpg?height=153&width=603&top_left_y=520&top_left_x=479)
(c)
$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH} \xrightarrow{?} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CD}$
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0303.jpg?height=142&width=604&top_left_y=528&top_left_x=1148)
(d)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0303.jpg?height=148&width=632&top_left_y=685&top_left_x=1191)


9-40 -

PROBLEM How would you prepare cyclodecyne starting from acetylene and any required alkyl halide?


9-40 -

PROBLEM The sex attractant given off by the common housefly is an alkene named muscalure. Propose a
9-45 synthesis of muscalure starting from acetylene and any alkyl halides needed. What is the IUPAC name for muscalure?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0303.jpg?height=139&width=456&top_left_y=1118&top_left_x=417)


9-40 -

Muscalure


General Problems -

PROBLEM A hydrocarbon of unknown structure has the formula $\mathrm{C}_{8} \mathrm{H}_{10}$. On catalytic hydrogenation over the
9-46 Lindlar catalyst, 1 equivalent of $\mathrm{H}_{2}$ is absorbed. On hydrogenation over a palladium catalyst, 3 equivalents of $\mathrm{H}_{2}$ are absorbed.
(a) How many degrees of unsaturation are present in the unknown structure?
(b) How many triple bonds are present? (c) How many double bonds are present?
(d) How many rings are present? (e) Draw a structure that fits the data.


General Problems -

PROBLEM Compound $\mathbf{A}\left(\mathrm{C}_{9} \mathrm{H}_{12}\right)$ absorbed 3 equivalents of $\mathrm{H}_{2}$ on catalytic reduction over a palladium catalyst
9-47 to give $\mathbf{B}\left(\mathrm{C}_{9} \mathrm{H}_{18}\right)$. On ozonolysis, compound $\mathbf{A}$ gave, among other things, a ketone that was identified as cyclohexanone. On treatment with $\mathrm{NaNH}_{2}$ in $\mathrm{NH}_{3}$, followed by addition of iodomethane, compound $\mathbf{A}$ gave a new hydrocarbon, $\mathbf{C}\left(\mathrm{C}_{10} \mathrm{H}_{14}\right)$. What are the structures of $\mathbf{A}, \mathbf{B}$, and $\mathbf{C}$ ?

PROBLEM Hydrocarbon $A$ has the formula $\mathrm{C}_{12} \mathrm{H}_{8}$. It absorbs 8 equivalents of $\mathrm{H}_{2}$ on catalytic reduction over
9-48 a palladium catalyst. On ozonolysis, only two products are formed: oxalic acid $\left(\mathrm{HO}_{2} \mathrm{CCO}_{2} \mathrm{H}\right)$ and succinic acid $\left(\mathrm{HO}_{2} \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}\right)$. Write the reactions, and propose a structure for $\mathbf{A}$.


General Problems -

PROBLEM Occasionally, a chemist might need to invert the stereochemistry of an alkene-that is, to convert
9-49 a cis alkene to a trans alkene, or vice versa. There is no one-step method for doing an alkene inversion, but the transformation can be carried out by combining several reactions in the proper sequence. How would you carry out the following reactions?
(a)
(b) cis-5-Decene $\xrightarrow{?}$ trans-5-Decene
trans-5-Decene $\xrightarrow{?}$ cis-5-Decene


General Problems -

PROBLEM Organometallic reagents such as sodium acetylide undergo an addition reaction with ketones,
9-50 giving alcohols:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0303.jpg?height=133&width=603&top_left_y=2373&top_left_x=411)


General Problems -

How might you use this reaction to prepare 2-methyl-1,3-butadiene, the starting material used in the manufacture of synthetic rubber?


General Problems -


Mestranol -

PROBLEM 1-Octen-3-ol, a potent mosquito attractant commonly used in mosquito traps, can be prepared in 9-52 two steps from hexanal, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CHO}$. The first step is an acetylide-addition reaction like that described in Problem 9-50. What is the structure of the product from the first step, and how can it be converted into 1-octen-3-ol?
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Mestranol -


Mestranol -

PROBLEM Erythrogenic acid, $\mathrm{C}_{18} \mathrm{H}_{26} \mathrm{O}_{2}$, is an acetylenic fatty acid that turns a vivid red on exposure to
9-53 light. On catalytic hydrogenation over a palladium catalyst, 5 equivalents of $\mathrm{H}_{2}$ are absorbed, and stearic acid, $\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{16} \mathrm{CO}_{2} \mathrm{H}$, is produced. Ozonolysis of erythrogenic acid gives four products: formaldehyde, $\mathrm{CH}_{2} \mathrm{O}$; oxalic acid, $\mathrm{HO}_{2} \mathrm{CCO}_{2} \mathrm{H}$; azelaic acid, $\mathrm{HO}_{2} \mathrm{C}\left(\mathrm{CH}_{2}\right)_{7} \mathrm{CO}_{2} \mathrm{H}$; and the aldehyde acid $\mathrm{OHC}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CO}_{2} \mathrm{H}$. Draw two possible structures for erythrogenic acid, and suggest a way to tell them apart by carrying out some simple reactions.


Mestranol -

PROBLEM Hydrocarbon $\mathbf{A}$ has the formula $\mathrm{C}_{9} \mathrm{H}_{12}$ and absorbs 3 equivalents of $\mathrm{H}_{2}$ to yield $\mathbf{B}, \mathrm{C}_{9} \mathrm{H}_{18}$, when
9-54 hydrogenated over a $\mathrm{Pd} / \mathrm{C}$ catalyst. On treatment of $\mathbf{A}$ with aqueous $\mathrm{H}_{2} \mathrm{SO}_{4}$ in the presence of mercury(II), two isomeric ketones, $\mathbf{C}$ and $\mathbf{D}$, are produced. Oxidation of $\mathbf{A}$ with $\mathrm{KMnO}_{4}$ gives a mixture of acetic acid $\left(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\right)$ and the tricarboxylic acid $\mathbf{E}$. Propose structures for compounds $\mathbf{A}-\mathbf{D}$, and write the reactions.
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Mestranol -

E
PROBLEM A cumulene is a compound with three adjacent double bonds. Draw an orbital picture of a
9-55 cumulene. What kind of hybridization do the two central carbon atoms have? What is the geometric relationship of the substituents on one end to the substituents on the other end? What kind of isomerism is possible? Make a model to help see the answer.
$\mathrm{R}_{2} \mathrm{C}=\mathrm{C}=\mathrm{C}=\mathrm{CR}_{2}$


A cumulene -

PROBLEM Which of the following bases could be used to deprotonate 1-butyne?


9-56 -


CHAPTER 10 <br> Organohalides -


CHAPTER 10 <br> Organohalides -

FIGURE 10.1 The gases released during volcanic eruptions contain large amounts of organohalides, including chloromethane, chloroform, dichlorodifluoromethane, and many others. (credit: modification of work "Tavurvur volcano" by Taro Taylor, Richard Bartz/ Wikimedia Commons, CC BY 2.0)


CHAPTER CONTENTS -

10.1 Names and Structures of Alkyl Halides
10.2 Preparing Alkyl Halides from Alkanes: Radical Halogenation
10.3 Preparing Alkyl Halides from Alkenes: Allylic Bromination
10.4 Stability of the Allyl Radical: Resonance Revisited
10.5 Preparing Alkyl Halides from Alcohols
10.6 Reactions of Alkyl Halides: Grignard Reagents
10.7 Organometallic Coupling Reactions
10.8 Oxidation and Reduction in Organic Chemistry


CHAPTER CONTENTS -

WHY THIS CHAPTER? Alkyl halides are encountered less frequently than their oxygen-containing relatives and are not often involved in the biochemical pathways of terrestrial organisms, but some of the kinds of reactions they undergo-nucleophilic substitutions and eliminations-are encountered frequently. Thus, alkyl halide chemistry is a relatively simple model for many mechanistically similar but structurally more complex reactions found in biomolecules. We'll begin this chapter with a look at how to name and prepare alkyl halides, and we'll see several of their reactions. Then, in the next chapter, we'll make a detailed study of the substitution and elimination reactions of alkyl halides-two of the most important and well-studied reaction types in organic chemistry.


CHAPTER CONTENTS -

Now that we've covered the chemistry of hydrocarbons, it's time to start looking at more complex substances that contain elements in addition to C and H . We'll begin by discussing the chemistry of organohalides,
compounds that contain one or more halogen atoms.
Halogen-substituted organic compounds are widespread in nature, and more than 5000 organohalides have been found in algae and various other marine organisms. Chloromethane, for instance, is released in large amounts by ocean kelp, as well as by forest fires and volcanoes. Halogen-containing compounds also have an array of industrial applications, including their use as solvents, inhaled anesthetics in medicine, refrigerants, and pesticides.
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Trichloroethylene (a solvent)
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Halothane (an inhaled anesthetic)
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Tetrafluoropropene (a refrigerant)
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CHAPTER CONTENTS -

Bromomethane (a fumigant)


CHAPTER CONTENTS -

Still other halo-substituted compounds are used as medicines and food additives. The nonnutritive sweetener sucralose, marketed as Splenda, contains three chlorine atoms, for instance. Sucralose is about 600 times as sweet as sucrose, so only 1 mg is equivalent to an entire teaspoon of table sugar.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0307.jpg?height=218&width=554&top_left_y=940&top_left_x=783)