Terpenes: Naturally Occurring Alkenes -

Dimethylallyl diphosphate


Key Terms -

- anti stereochemistry
- bromonium ion
- carbene, $\mathrm{R}_{2} \mathrm{C}$
- chain-growth polymer
- epoxide
- glycol
- halohydrin
- hydroboration
- hydrogenated
- hydroxylation
- monomer
- oxidation
- oxirane
- oxymercuration-demercuration
- ozonide
- polymer
- reduction
- Simmons-Smith reaction
- stereospecific
- syn stereochemistry


Key Terms -


Summary -

With the background needed to understand organic reactions now covered, this chapter has begun the systematic description of major functional groups.
Alkenes are generally prepared by an elimination reaction, such as dehydrohalogenation, the elimination of HX from an alkyl halide, or dehydration, the elimination of water from an alcohol. The converse of this elimination reaction is the addition of various substances to the alkene double bond to give saturated products.
$\mathrm{HCl}, \mathrm{HBr}$, and HI add to alkenes by a two-step electrophilic addition mechanism. Initial reaction of the nucleophilic double bond with $\mathrm{H}^{+}$gives a carbocation intermediate, which then reacts with halide ion. Bromine and chlorine add to alkenes via three-membered-ring bromonium ion or chloronium ion intermediates to give addition products having anti stereochemistry. If water is present during the halogen addition reaction, a halohydrin is formed.


Summary -

Hydration of an alkene-the addition of water-is carried out by either of two procedures, depending on the product desired. Oxymercuration-demercuration involves electrophilic addition of $\mathrm{Hg}^{2+}$ to an alkene, followed by trapping of the cation intermediate with water and subsequent treatment with $\mathrm{NaBH}_{4}$. Hydroboration involves addition of borane $\left(\mathrm{BH}_{3}\right)$ followed by oxidation of the intermediate organoborane with alkaline $\mathrm{H}_{2} \mathrm{O}_{2}$. The two hydration methods are complementary: oxymercuration-demercuration gives the product of Markovnikov addition, whereas hydroboration-oxidation gives the product with non-Markovnikov syn stereochemistry.


Summary -

Alkenes are reduced by addition of $\mathrm{H}_{2}$ in the presence of a catalyst such as platinum or palladium to yield alkanes, a process called catalytic hydrogenation. Alkenes are also oxidized by reaction with a peroxyacid to give epoxides, which can be converted into trans-1,2-diols by acid-catalyzed hydrolysis. The corresponding cis-1,2-diols can be made directly from alkenes by hydroxylation with $\mathrm{OsO}_{4}$. Alkenes can also be cleaved to produce carbonyl compounds by reaction with ozone, followed by reduction with zinc metal. In addition, alkenes react with divalent substances called carbenes, $\mathbf{R}_{\mathbf{2}} \mathbf{C}$ :, to give cyclopropanes. Nonhalogenated cyclopropanes are best prepared by treatment of the alkene with $\mathrm{CH}_{2} \mathrm{I}_{2}$ and zinc-copper, a process called the Simmons-Smith reaction.


Summary -

Alkene polymers-large molecules resulting from repetitive bonding of many hundreds or thousands of small monomer units-are formed by chain-reaction polymerization of simple alkenes. Polyethylene, polypropylene, and polystyrene are examples. As a general rule, radical addition reactions are not common in the laboratory but occur frequently in biological pathways.


Summary -

Many reactions give chiral products. If the reactants are optically inactive, the products are also optically inactive. If one or both of the reactants is optically active, the products can also be optically active.


LEARNING REACTIONS -

What's seven times nine? Sixty-three, of course. You didn't have to stop and figure it out; you knew the answer immediately because you long ago learned the multiplication tables. Learning the reactions of organic chemistry requires the same approach: reactions have to be learned for quick recall if they are to be useful.


LEARNING REACTIONS -

Different people take different approaches to learning reactions. Some people make flashcards; others find studying with friends to be helpful. To help guide your study, most chapters in this book end with a summary of the reactions just presented. In addition, the accompanying Study Guide and Student Solutions Manual has several appendixes that organize organic reactions from other perspectives. Fundamentally, though, there are no shortcuts. Learning organic chemistry does take effort.


Summary of Reactions -

No stereochemistry is implied unless specifically indicated with wedged, solid, and dashed lines.


Summary of Reactions -

1. Addition reactions of alkenes
a. Addition of $\mathrm{HCl}, \mathrm{HBr}$, and HI (Section 7.7 and Section 7.8)


Summary of Reactions -

Markovnikov regiochemistry occurs, with H adding to the less highly substituted alkene carbon and halogen adding to the more highly substituted carbon.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0268.jpg?height=131&width=456&top_left_y=322&top_left_x=886)
b. Addition of halogens $\mathrm{Cl}_{2}$ and $\mathrm{Br}_{2}$ (Section 8.2)


Summary of Reactions -

Anti addition is observed through a halonium ion intermediate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0268.jpg?height=136&width=529&top_left_y=539&top_left_x=847)
c. Halohydrin formation (Section 8.3)


Summary of Reactions -


Summary of Reactions -

Syn addition occurs.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0268.jpg?height=129&width=578&top_left_y=1410&top_left_x=822)
g. Epoxidation with a peroxyacid (Section 8.7)

Syn addition occurs.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0268.jpg?height=150&width=529&top_left_y=1627&top_left_x=847)
h. Hydroxylation with $\mathrm{OsO}_{4}$ (Section 8.7)


Summary of Reactions -

Syn addition occurs.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0268.jpg?height=142&width=659&top_left_y=1859&top_left_x=779)
i. Addition of carbenes to yield cyclopropanes (Section 8.9)
(1) Dichlorocarbene addition
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0268.jpg?height=185&width=665&top_left_y=2106&top_left_x=779)
(2) Simmons-Smith reaction
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0268.jpg?height=172&width=681&top_left_y=2359&top_left_x=771)
2. Hydroxylation by acid-catalyzed epoxide hydrolysis (Section 8.7)


Summary of Reactions -

Anti stereochemistry occurs.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0269.jpg?height=142&width=502&top_left_y=281&top_left_x=844)
3. Oxidative cleavage of alkenes (Section 8.8)
a. Reaction with ozone followed by zinc in acetic acid
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0269.jpg?height=140&width=698&top_left_y=510&top_left_x=768)
b. Reaction with $\mathrm{KMnO}_{4}$ in acidic solution
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0269.jpg?height=142&width=722&top_left_y=691&top_left_x=750)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0269.jpg?height=142&width=709&top_left_y=878&top_left_x=757)
4. Cleavage of 1,2 -diols (Section 8.8)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0269.jpg?height=134&width=635&top_left_y=1088&top_left_x=780)


Additional Problems -


Visualizing Chemistry -

PROBLEM Name the following alkenes, and predict the products of their reaction with (1)
8-22 meta-chloroperoxybenzoic acid, (2) $\mathrm{KMnO}_{4}$ in aqueous acid, (3) $\mathrm{O}_{3}$, followed by Zn in acetic acid:
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0269.jpg?height=391&width=543&top_left_y=1458&top_left_x=482)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0269.jpg?height=282&width=386&top_left_y=1469&top_left_x=1103)


Visualizing Chemistry -

PROBLEM Draw the structures of alkenes that would yield the following alcohols on hydration (red = 0). Tell in
8-23 each case whether you would use hydroboration-oxidation or oxymercuration-demercuration.
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0269.jpg?height=328&width=457&top_left_y=1983&top_left_x=490)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0269.jpg?height=304&width=432&top_left_y=1992&top_left_x=1020)


Visualizing Chemistry -

PROBLEM The following alkene undergoes hydroboration-oxidation to yield a single product rather than a
8-24 mixture. Explain the result, and draw the product showing its stereochemistry.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0270.jpg?height=386&width=364&top_left_y=195&top_left_x=433)


Visualizing Chemistry -

PROBLEM From what alkene was the following 1,2-diol made, and what method was used, epoxide hydrolysis $\mathbf{8 - 2 5}$ or $\mathrm{OsO}_{4}$ ?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0270.jpg?height=331&width=468&top_left_y=729&top_left_x=430)


Mechanism Problems -


Mechanism Problems -

PROBLEM Draw the structures of the organoboranes formed when borane reacts with the following alkenes,
8-27 including the regiochemistry and stereochemistry as appropriate. Propose a mechanism for each reaction.
(a)
<img class="imgSvg" id = "m6sn3naf8azyuciav05" 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(b)
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(c)
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Mechanism Problems -

PROBLEM Which of the reactions below would result in a product mixture that would rotate plane-polarized 8-30 light?
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0271.jpg?height=270&width=389&top_left_y=315&top_left_x=456)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0271.jpg?height=147&width=465&top_left_y=311&top_left_x=884)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0271.jpg?height=117&width=495&top_left_y=581&top_left_x=468)


Mechanism Problems -

PROBLEM Reaction of 2-methylpropene with $\mathrm{CH}_{3} \mathrm{OH}$ in the presence of $\mathrm{H}_{2} \mathrm{SO}_{4}$ catalyst yields methyl tert-butyl
8-31 ether, $\mathrm{CH}_{3} \mathrm{OC}\left(\mathrm{CH}_{3}\right)_{3}$, by a mechanism analogous to that of acid-catalyzed alkene hydration. Write the mechanism, using curved arrows for each step.


Mechanism Problems -

PROBLEM Iodine azide, $\mathrm{IN}_{3}$, adds to alkenes by an electrophilic mechanism similar to that of bromine. If a
8-32 monosubstituted alkene such as 1-butene is used, only one product results:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0271.jpg?height=104&width=871&top_left_y=997&top_left_x=416)
(a) Add lone-pair electrons to the structure shown for $\mathrm{IN}_{3}$, and draw a second resonance form for the molecule.
(b) Calculate formal charges for the atoms in both resonance structures you drew for $\mathrm{IN}_{3}$ in part (a).
(c) In light of the result observed when $\mathrm{IN}_{3}$ adds to 1-butene, what is the polarity of the $\mathrm{I}-\mathrm{N}_{3}$ bond? Propose a mechanism for the reaction using curved arrows to show the electron flow in each step.


Mechanism Problems -

PROBLEM 10-Bromo- $\alpha$-chamigrene, a compound isolated from marine algae, is thought to be biosynthesized
8-33 from $\gamma$-bisabolene by the following route:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0271.jpg?height=378&width=1454&top_left_y=1535&top_left_x=409)


Mechanism Problems -

Draw the structures of the intermediate bromonium and cyclic carbocation, and propose mechanisms for all three steps.


Mechanism Problems -

PROBLEM Isolated from marine algae, prelaureatin is thought to be biosynthesized from laurediol by the
8-34 following route. Propose a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0271.jpg?height=370&width=907&top_left_y=2138&top_left_x=411)


Mechanism Problems -

PROBLEM Dichlorocarbene can be generated by heating sodium trichloroacetate. Propose a mechanism for
8-35 the reaction, and use curved arrows to indicate the movement of electrons in each step. What relationship does your mechanism bear to the base-induced elimination of HCl from chloroform?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0272.jpg?height=172&width=828&top_left_y=348&top_left_x=418)


Mechanism Problems -

PROBLEM Reaction of cyclohexene with mercury(II) acetate in $\mathrm{CH}_{3} \mathrm{OH}$ rather than $\mathrm{H}_{2} \mathrm{O}$, followed by treatment 8-36 with $\mathrm{NaBH}_{4}$, yields cyclohexyl methyl ether rather than cyclohexanol. Suggest a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0272.jpg?height=146&width=666&top_left_y=648&top_left_x=445)


Mechanism Problems -

Cyclohexene
Cyclohexyl methyl ether


Mechanism Problems -

PROBLEM Use your general knowledge of alkene chemistry to suggest a mechanism for the following reaction.
8-37
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0272.jpg?height=261&width=874&top_left_y=973&top_left_x=409)


Mechanism Problems -

PROBLEM Treatment of 4-penten-1-ol with aqueous $\mathrm{Br}_{2}$ yields a cyclic bromo ether rather than the expected
8-38 bromohydrin. Suggest a mechanism, using curved arrows to show electron movement.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0272.jpg?height=109&width=760&top_left_y=1366&top_left_x=417)

4-Penten-1-ol 2-(Bromomethyl)tetrahydrofuran
PROBLEM Hydroboration of 2-methyl-2-pentene at $25{ }^{\circ} \mathrm{C}$, followed by oxidation with alkaline $\mathrm{H}_{2} \mathrm{O}_{2}$, yields
8-39 2-methyl-3-pentanol, but hydroboration at $160{ }^{\circ} \mathrm{C}$ followed by oxidation yields 4-methyl-1-pentanol. Suggest a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0272.jpg?height=375&width=909&top_left_y=1710&top_left_x=418)


Reactions of Alkenes -

PROBLEM Predict the products of the following reactions (the aromatic ring is unreactive in all cases). Indicate
8-40 regiochemistry when relevant.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0273.jpg?height=522&width=743&top_left_y=181&top_left_x=409)


Reactions of Alkenes -


Reactions of Alkenes -

PROBLEM Which reaction would you expect to be faster, addition of HBr to cyclohexene or to
8-43 1-methylcyclohexene? Explain.
PROBLEM What product will result from hydroboration-oxidation of 1-methylcyclopentene with deuterated
8-44 borane, $\mathrm{BD}_{3}$ ? Show both the stereochemistry (spatial arrangement) and the regiochemistry (orientation) of the product.


Reactions of Alkenes -

PROBLEM The cis and trans isomers of 2-butene give different cyclopropane products in the Simmons-Smith
8-45 reaction. Show the structures of both, and explain the difference.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0273.jpg?height=150&width=592&top_left_y=2126&top_left_x=414)


Reactions of Alkenes -

PROBLEM Predict the products of the following reactions. Don't worry about the size of the molecule;
8-46 concentrate on the functional groups.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0274.jpg?height=450&width=996&top_left_y=187&top_left_x=413)


Reactions of Alkenes -

PROBLEM Addition of HCl to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclohexane as a sole product.
8-47 Use resonance structures of the carbocation intermediate to explain why none of the alternate regioisomer is formed.
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$\xrightarrow{\mathrm{HCl}}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0274.jpg?height=33&width=72&top_left_y=894&top_left_x=723)


Reactions of Alkenes -

1-Chloro-1-methoxy-
cyclohexane


Reactions of Alkenes -

Synthesis Using Alkenes
PROBLEM How would you carry out the following transformations? What reagents would you use in each case?