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Chapter 25: Problem 36

Describe the intermediate that is thought to form in the addition of a hydrogen halide to an alkene, using cyclohexene as the alkene in your description.

Short Answer

Expert verified
The intermediate formed during the addition of a hydrogen halide to cyclohexene is a carbocation, with the structure: \( \chemfig{ *6(=-=(-[+])-=-=) } \) This species is generated after the alkene's double bond attacks the electropositive hydrogen atom in the hydrogen halide, breaking its bond with the halogen atom. The carbocation then reacts with the negatively charged halide anion to form the final product of the reaction.

Step by step solution

01

Identify the reactants

In this reaction, the reactants are cyclohexene (an alkene) and a hydrogen halide (HX, where X could be a halogen atom like Cl, Br or I). Cyclohexene: \( \chemfig{*6(=-=-=-)} \) HX: H-X
02

Understand the reaction mechanism

The reaction mechanism for the addition of a hydrogen halide to an alkene is an electrophilic addition reaction. In this mechanism, the double bond of the alkene will attack the hydrogen atom of the hydrogen halide, breaking its bond with the halogen atom. This leads to the formation of a carbocation, which is a species with a positive charge on a carbon atom. The halogen anion then attacks the carbocation to form the final product.
03

Describe the attack of the alkene double bond on the hydrogen atom

Initially, the pi electrons in the alkene's double bond will be attracted to the electropositive hydrogen atom in the hydrogen halide, forming a new bond between the hydrogen atom and one of the carbons of the alkene. This breaks the bond between hydrogen and halogen, leaving a negatively charged halide anion (X^-) and generating a carbocation intermediate.
04

Describe the formation of the carbocation intermediate

When the pi bond in the cyclohexene attacks the hydrogen atom in the hydrogen halide, the cyclohexene loses its double bond and forms a carbocation intermediate. This intermediate has a positive charge on the carbon atom that was part of the double bond but did not form a new bond with the hydrogen atom. The carbocation intermediate formed looks like this: \( \chemfig{ *6(=-=(-[+])-=-=) } \)
05

Describe the attack of the halide anion on the carbocation

Finally, the negatively charged halide anion (X^-) that was produced earlier will attack the positively charged carbon atom in the carbocation intermediate. This leads to the formation of a new bond between the carbon and the halogen atom, yielding the final product of the addition reaction between cyclohexene and the hydrogen halide. In conclusion, the intermediate formed during the addition of a hydrogen halide to cyclohexene is a carbocation, which looks like this: \( \chemfig{ *6(=-=(-[+])-=-=) } \)

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Most popular questions from this chapter

Imagine a single DNA strand containing a section with the following base sequence: \(5^{\prime}\) -GCATTGGC-3'. What is the base sequence of the complementary strand? (The two strands of DNA will come together in an antiparallel fashion: that is, \(5^{\prime}-\mathrm{TAG}-3^{\prime}\) will bind to \(3^{\prime}-\mathrm{ATC}-5^{\prime} .\) )

What are the characteristic hybrid orbitals employed by (a) carbon in an alkane, (b) carbon in a double bond in an alkene, (c) carbon in the benzene ring, (d) carbon in a triple bond in an alkyne?

(a) What is the difference between a straight-chain and branched-chain alkane? (b) What is the difference between an alkane and an alkyl group? (c) Why are alkanes said to be saturated? (d) Give an example of an unsaturated molecule.

Does 3-chloro-3-methylhexane have optical isomers? Why or why not?

(a) When cyclopropane is treated with HI, 1-iodopropane is formed. A similar type of reaction does not occur with cyclopentane or cyclohexane. How do you account for the reactivity of cyclopropane? (b) Suggest a method of preparing ethylbenzene, starting with benzene and ethylene as the only organic reagents.
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