General Problems -

PROBLEM Retin A, or retinoic acid, is a medication commonly used to reduce wrinkles and treat severe acne.
7-63 How many different isomers arising from $E, Z$ double-bond isomerizations are possible?
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Retin A (retinoic acid)
PROBLEM Fucoserratene and ectocarpene are sex pheromones produced by marine brown algae. What are
7-64 their systematic names? (Ectocarpene is difficult; make your best guess, and then check your answer in the Student Solutions Manual.)
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Fucoserratene
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General Problems -

Ectocarpene


General Problems -

PROBLEM tert-Butyl esters $\left[\mathrm{RCO}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\right]$ are converted into carboxylic acids $\left(\mathrm{RCO}_{2} \mathrm{H}\right)$ by reaction with
7-65 trifluoroacetic acid, a reaction useful in protein synthesis (Section 26.7). Assign $E, Z$ designation to the double bonds of both reactant and product in the following scheme, and explain why there is an apparent change in double-bond stereochemistry:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0233.jpg?height=237&width=1101&top_left_y=2082&top_left_x=417)


General Problems -

PROBLEM Vinylcyclopropane reacts with HBr to yield a rearranged alkyl bromide. Follow the flow of electrons
7-66 as represented by the curved arrows, show the structure of the carbocation intermediate in brackets, and show the structure of the final product.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0234.jpg?height=177&width=679&top_left_y=188&top_left_x=460)


Vinylcyclopropane -

PROBLEM Calculate the degree of unsaturation in each of the following formulas:
7-67 (a) Cholesterol, $\mathrm{C}_{27} \mathrm{H}_{46} \mathrm{O}$ (b) DDT, $\mathrm{C}_{14} \mathrm{H}_{9} \mathrm{Cl}_{5}$ (c) Prostaglandin $\mathrm{E}_{1}, \mathrm{C}_{20} \mathrm{H}_{34} \mathrm{O}_{5}$
(d) Caffeine, $\mathrm{C}_{8} \mathrm{H}_{10} \mathrm{~N}_{4} \mathrm{O}_{2}$
(e) Cortisone, $\mathrm{C}_{21} \mathrm{H}_{28} \mathrm{O}_{5}$ (f) Atropine, $\mathrm{C}_{17} \mathrm{H}_{23} \mathrm{NO}_{3}$


Vinylcyclopropane -

PROBLEM The isobutyl cation spontaneously rearranges to the tert-butyl cation by a hydride shift. Is the
7-68 rearrangement exergonic or endergonic? Draw what you think the transition state for the hydride shift might look like according to the Hammond postulate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0234.jpg?height=245&width=592&top_left_y=756&top_left_x=414)


Vinylcyclopropane -

PROBLEM Draw an energy diagram for the addition of HBr to 1-pentene. Let one curve on your diagram
7-69 show the formation of 1-bromopentane product and another curve on the same diagram show the formation of 2-bromopentane product. Label the positions for all reactants, intermediates, and products. Which curve has the higher-energy carbocation intermediate? Which curve has the higher-energy first transition state?
PROBLEM Sketch the transition-state structures involved in the reaction of HBr with 1-pentene (Problem
7-70 7-69). Tell whether each structure resembles reactant or product.
PROBLEM Aromatic compounds such as benzene react with alkyl chlorides in the presence of $\mathrm{AlCl}_{3}$ catalyst to
7-71 yield alkylbenzenes. This reaction occurs through a carbocation intermediate, formed by reaction of the alkyl chloride with $\mathrm{AlCl}_{3}\left(\mathrm{R}-\mathrm{Cl}+\mathrm{AlCl}_{3} \longrightarrow \mathrm{R}^{+}+\mathrm{AlCl}_{4}{ }^{-}\right)$. How can you explain the observation that reaction of benzene with 1-chloropropane yields isopropylbenzene as the major product?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0234.jpg?height=202&width=793&top_left_y=1558&top_left_x=411)


Vinylcyclopropane -

PROBLEM Reaction of 2,3-dimethyl-1-butene with HBr leads to an alkyl bromide, $\mathrm{C}_{6} \mathrm{H}_{13} \mathrm{Br}$. On treatment of
7-72 this alkyl bromide with KOH in methanol, elimination of HBr occurs and a hydrocarbon that is isomeric with the starting alkene is formed. What is the structure of this hydrocarbon, and how do you think it is formed from the alkyl bromide?


CHAPTER 8 -


Alkenes: Reactions and Synthesis -


Alkenes: Reactions and Synthesis -

FIGURE 8.1 The Spectra fiber used to make the bulletproof vests used by police and military is made of ultra-high-molecular-weight polyethylene, a simple alkene polymer. (credit: modification of work "US Navy 081028-N-3857R-007 Seabees participate in a chemical, biological and radiological warfare drill" by U.S. Navy photo by Mass Communication Specialist 1st Class Chad Runge/Wikimedia Commons, Public Domain)


CHAPTER CONTENTS -

8.1 Preparing Alkenes: A Preview of Elimination Reactions
8.2 Halogenation of Alkenes: Addition of $X_{2}$
8.3 Halohydrins from Alkenes: Addition of HO-X
8.4 Hydration of Alkenes: Addition of $\mathrm{H}_{2} \mathrm{O}$ by Oxymercuration
8.5 Hydration of Alkenes: Addition of $\mathrm{H}_{2} \mathrm{O}$ by Hydroboration
8.6 Reduction of Alkenes: Hydrogenation
8.7 Oxidation of Alkenes: Epoxidation and Hydroxylation
8.8 Oxidation of Alkenes: Cleavage to Carbonyl Compounds
8.9 Addition of Carbenes to Alkenes: Cyclopropane Synthesis
8.10 Radical Additions to Alkenes: Chain-Growth Polymers
8.11 Biological Additions of Radicals to Alkenes
8.12 Reaction Stereochemistry: Addition of $\mathrm{H}_{2} \mathrm{O}$ to an Achiral Alkene
8.13 Reaction Stereochemistry: Addition of $\mathrm{H}_{2} \mathrm{O}$ to a Chiral Alkene


CHAPTER CONTENTS -

WHY THIS CHAPTER? Much of the background needed to understand organic reactions has now been covered, and it's time to begin a systematic description of the major functional groups. In this chapter on alkenes, and in future chapters on other functional groups, we'll discuss a variety of reactions, but try to focus on the general principles and patterns of reactivity that tie organic chemistry together. There are no shortcuts; you have to know the reactions to understand organic and biological chemistry.


CHAPTER CONTENTS -

Alkene addition reactions occur widely, both in the laboratory and in living organisms. Although we've studied
only the addition of HX thus far, many closely related reactions also take place. In this chapter, we'll see briefly how alkenes are prepared and we'll discuss further examples of alkene addition reactions. Particularly important are the addition of a halogen $\left(\mathrm{X}_{2}\right)$ to give a 1,2-dihalide, addition of a hypohalous acid (HOX) to give a halohydrin, addition of water to give an alcohol, addition of hydrogen to give an alkane, addition of a single oxygen to give a three-membered cyclic ether called an epoxide, and addition of two hydroxyl groups to give a 1,2-diol.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0236.jpg?height=825&width=861&top_left_y=474&top_left_x=632)


CHAPTER CONTENTS -

FIGURE 8.2 Some useful alkene reactions.


CHAPTER CONTENTS - 8.1 Preparing Alkenes: A Preview of Elimination Reactions

Before getting to the main subject of this chapter-the reactions of alkenes-let's take a brief look at how alkenes are prepared. The subject is a bit complex, though, so we'll return to it in Chapter 11 for a more detailed study. For the present, it's enough to realize that alkenes are readily available from simple precursors-usually alcohols in biological systems and either alcohols or alkyl halides in the laboratory.


Just as the chemistry of alkenes is dominated by addition reactions, the preparation of alkenes is dominated by elimination reactions. Additions and eliminations are, in many respects, two sides of the same coin. That is, an addition reaction might involve the addition of HBr or $\mathrm{H}_{2} \mathrm{O}$ to an alkene to form an alkyl halide or alcohol, whereas an elimination reaction might involve the loss of HBr or $\mathrm{H}_{2} \mathrm{O}$ from an alkyl halide or alcohol to form an alkene.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0236.jpg?height=125&width=708&top_left_y=1862&top_left_x=703)


The two most common elimination reactions are dehydrohalogenation-the loss of HX from an alkyl halide-and dehydration-the loss of water from an alcohol. Dehydrohalogenation usually occurs by reaction of an alkyl halide with strong base such as potassium hydroxide. For example, bromocyclohexane yields cyclohexene when treated with KOH in ethanol solution.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0236.jpg?height=205&width=871&top_left_y=2185&top_left_x=643)


Bromocyclohexane Cyclohexene (81\%)
Dehydration is often carried out in the laboratory by treatment of an alcohol with a strong acid. For example, when 1-methylcyclohexanol is warmed with aqueous sulfuric acid in tetrahydrofuran (THF) solvent, loss of
water occurs and 1-methylcyclohexene is formed.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0237.jpg?height=171&width=812&top_left_y=256&top_left_x=678)


1-Methylcyclohexanol
1-Methylcyclohexene (91\%)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0237.jpg?height=147&width=774&top_left_y=520&top_left_x=643)


In biological pathways, dehydrations rarely occur with isolated alcohols. Instead, they normally take place on substrates in which the -OH is positioned two carbons away from a $\mathrm{C}=\mathrm{O}$ group. In the biosynthesis of fats, for instance, $\beta$-hydroxybutyryl ACP is converted by dehydration to trans-crotonyl ACP, where ACP is an abbreviation for acyl carrier protein. We'll see the reason for this requirement in Section 11.10.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0237.jpg?height=172&width=874&top_left_y=860&top_left_x=628)
$\boldsymbol{\beta}$-Hydroxybutyryl ACP
trans-Crotonyl ACP
PROBLEM One problem with elimination reactions is that mixtures of products are often formed. For example,
8-1 treatment of 2-bromo-2-methylbutane with KOH in ethanol yields a mixture of two alkene products. What are their likely structures?


PROBLEM How many alkene products, including $E, Z$ isomers, might be obtained by dehydration of 8-2 3-methyl-3-hexanol with aqueous sulfuric acid?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0237.jpg?height=156&width=505&top_left_y=1364&top_left_x=414)


3-Methyl-3-hexanol -


3-Methyl-3-hexanol - 8.2 Halogenation of Alkenes: Addition of $X_{2}$

Bromine and chlorine add rapidly to alkenes to yield 1,2-dihalides, a process called halogenation. For example, nearly 50 million tons of 1,2-dichloroethane (ethylene dichloride) are synthesized worldwide each year, much of it by addition of $\mathrm{Cl}_{2}$ to ethylene. The product is used both as a solvent and as starting material for the manufacture of poly(vinyl chloride), PVC, the third most widely synthesized polymer in the world afterpolyethelyne and polypropolyne. Fluorine is too reactive and difficult to control for most laboratory applications, and iodine does not react with most alkenes.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0237.jpg?height=158&width=611&top_left_y=1951&top_left_x=730)


Ethylene
1,2-Dichloroethane (ethylene dichloride)
Based on what we've seen thus far, a possible mechanism for the reaction of bromine with alkenes might involve electrophilic addition of $\mathrm{Br}^{+}$to the alkene, giving a carbocation intermediate that could undergo further reaction with $\mathrm{Br}^{-}$to yield the dibromo addition product.


Possible -


Possible -

Although this mechanism seems plausible, it's not fully consistent with known facts. In particular, it doesn't explain the stereochemistry of the addition reaction. That is, the mechanism doesn't account for which product stereoisomer is formed.


Possible -

When the halogenation reaction is carried out on a cycloalkene, such as cyclopentene, only the trans stereoisomer of the dihalide addition product is formed, rather than the mixture of cis and trans isomers that might have been expected if a planar carbocation intermediate were involved. We say that the reaction occurs with anti stereochemistry, meaning that the two bromine atoms come from opposite faces of the double bond-one from the top face and one from the bottom face.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0238.jpg?height=343&width=989&top_left_y=834&top_left_x=568)


Possible -

An explanation for the observed stereochemistry of addition was suggested in 1937 by George Kimball and Irving Roberts, who proposed that the reaction intermediate is not a carbocation but is instead a bromonium ion, $\mathbf{R}_{\mathbf{2}} \mathbf{B r}^{+}$, formed by electrophilic addition of $\mathrm{Br}^{+}$to the alkene. (Similarly, a chloronium ion contains a positively charged, divalent chlorine, $\mathrm{R}_{2} \mathrm{Cl}^{+}$.) The bromonium ion is formed in a single step by interaction of the alkene with $\mathrm{Br}_{2}$ and the simultaneous loss of $\mathrm{Br}^{-}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0238.jpg?height=307&width=646&top_left_y=1402&top_left_x=734)

How does the formation of a bromonium ion account for the observed anti stereochemistry of addition to cyclopentene? If a bromonium ion is formed as an intermediate, we can imagine that the large bromine atom might "shield" one side of the molecule. Reaction with $\mathrm{Br}^{-}$ion in the second step could then occur only from the opposite, unshielded side to give the trans product.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0239.jpg?height=863&width=1039&top_left_y=189&top_left_x=538)


Possible -

The bromonium ion postulate, made more than 85 years ago to explain the stereochemistry of halogen addition to alkenes, is a remarkable example of deductive logic in chemistry. Arguing from experimental results, chemists were able to make a hypothesis about the intimate mechanistic details of alkene electrophilic reactions. Subsequently, strong evidence supporting the mechanism came from the work of George Olah at the University of Southern California, who prepared and studied stable solutions of cyclic bromonium ions in liquid $\mathrm{SO}_{2}$. There's no question that bromonium ions exist.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0239.jpg?height=279&width=799&top_left_y=1354&top_left_x=658)


Possible -

Alkene halogenation reactions occur in nature just as they do in the laboratory but are limited primarily to marine organisms living in halide-rich environments. These biological halogenation reactions are carried out by enzymes called haloperoxidases, which use $\mathrm{H}_{2} \mathrm{O}_{2}$ to oxidize $\mathrm{Br}^{-}$or $\mathrm{Cl}^{-}$ions to a biological equivalent of $\mathrm{Br}^{+}$or $\mathrm{Cl}^{+}$. Electrophilic addition to the double bond of a substrate molecule then yields a bromonium or chloronium ion intermediate just as in the laboratory, and reaction with another halide ion completes the process. Halomon, for example, an antitumor pentahalide isolated from red alga, is thought to arise by a route that involves twofold addition of BrCl through the corresponding bromonium ions.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0239.jpg?height=166&width=543&top_left_y=1961&top_left_x=601)
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Possible -

Halomon
PROBLEM What product would you expect to obtain from addition of $\mathrm{Cl}_{2}$ to 1,2 -dimethylcyclohexene? Show 8-3 the stereochemistry of the product.

PROBLEM Addition of HCl to 1,2-dimethylcyclohexene yields a mixture of two products. Show the 8-4 stereochemistry of each, and explain why a mixture is formed.


Possible - 8.3 Halohydrins from Alkenes: Addition of HO-X

Another example of an electrophilic addition is the reaction an alkene with either $\mathrm{Br}_{2}$ or $\mathrm{Cl}_{2}$ in the presence of
water to yield a 1,2-halo alcohol, called a halohydrin.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0240.jpg?height=132&width=245&top_left_y=262&top_left_x=772)


A halohydrin


We saw in the previous section that when $\mathrm{Br}_{2}$ reacts with an alkene, the cyclic bromonium ion intermediate reacts with the only nucleophile present, $\mathrm{Br}^{-}$ion. If the reaction is carried out in the presence of an additional nucleophile, however, the intermediate bromonium ion can be intercepted by the added nucleophile and diverted to a different product. In the presence of a high concentration of water, for instance, water competes with $\mathrm{Br}^{-}$ion as a nucleophile and reacts with the bromonium ion intermediate to yield a bromohydrin. The net effect is addition of $\mathrm{HO}-\mathrm{Br}$ to the alkene by the pathway shown in FIGURE 8.3.


FIGURE 8.3 MECHANISM


Bromohydrin formation by reaction of an alkene with $\mathrm{Br}_{2}$ in the presence of water.
Water acts as a nucleophile in step 2 to react with the intermediate bromonium ion.
(1) Reaction of the alkene with $\mathrm{Br}_{2}$ yields a bromonium ion intermediate, as previously discussed.
(2) Water acts as a nucleophile, using a lone pair of electrons to open the bromonium ion ring and form a bond to carbon. Since oxygen donates its electrons in this step, it now has the positive charge.
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(1) $\mathrm{Br}_{2}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0240.jpg?height=226&width=361&top_left_y=1253&top_left_x=1218)


2
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0240.jpg?height=196&width=321&top_left_y=1599&top_left_x=1216)


Loss of a proton $\left(\mathrm{H}^{+}\right)$from oxygen then gives $\mathrm{H}_{3} \mathrm{O}^{+}$and the neutral bromohydrin addition product.


(3) -


(3) -

In practice, few alkenes are soluble in water, and bromohydrin formation is often carried out in a solvent such as aqueous dimethyl sulfoxide, $\mathrm{CH}_{3} \mathrm{SOCH}_{3}$ (DMSO), using a reagent called N -bromosuccinimide (NBS) as a source of $\mathrm{Br}_{2}$. NBS is a stable, easily handled compound that slowly decomposes in water to yield $\mathrm{Br}_{2}$ at a controlled rate. Bromine itself can also be used in the addition reaction, but it is more dangerous and more difficult to handle than NBS.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0241.jpg?height=394&width=987&top_left_y=188&top_left_x=561)


(3) -

Notice that the aromatic ring in the above example does not react with $\mathrm{Br}_{2}$, even though it appears to have three carbon-carbon double bonds. As we'll see in Section 15.2, aromatic rings are a good deal more stable and less reactive than might be expected.


(3) -

There are a number of biological examples of halohydrin formation, particularly in marine organisms. As with halogenation (Section 8.2), halohydrin formation is carried out by haloperoxidases. For example:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0241.jpg?height=201&width=966&top_left_y=832&top_left_x=577)


(3) -

PROBLEM What product would you expect from the reaction of cyclopentene with NBS and water? Show the 8-5 stereochemistry.


(3) -

PROBLEM When an unsymmetrical alkene such as propene is treated with $N$-bromosuccinimide in aqueous
8-6 dimethyl sulfoxide, the major product has the bromine atom bonded to the less highly substituted carbon atom. Is this Markovnikov or non-Markovnikov orientation? (Section 7.8) Explain.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0241.jpg?height=93&width=576&top_left_y=1295&top_left_x=414)


(3) - 8.4 Hydration of Alkenes: Addition of $\mathrm{H}_{2} \mathrm{O}$ by Oxymercuration

Water adds to alkenes to yield alcohols, a process called hydration. The reaction takes place on treatment of the alkene with water and a strong acid catalyst, such as $\mathrm{H}_{2} \mathrm{SO}_{4}$, by a mechanism similar to that of HX addition. Thus, as shown in FIGURE 8.4, protonation of an alkene double bond yields a carbocation intermediate, which reacts with water to yield a protonated alcohol product, $\mathrm{ROH}_{2}{ }^{+}$. Loss of $\mathrm{H}^{+}$from this protonated alcohol gives the neutral alcohol and regenerates the acid catalyst.


FIGURE 8.4 MECHANISM -

Mechanism of the acid-catalyzed hydration of an alkene to yield an alcohol. Protonation of the alkene gives a carbocation intermediate, which reacts with water. The initial product is then deprotonated.