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Chapter 8: 8-5 (page 225)

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

Short Answer

Expert verified

The product formed by the reaction of cyclopentene with NBS and water is,

Step by step solution

01

Bromohydrins from alkenes

Bromohydrins formation takes place in the presence of an NBS reagent known as N-bromosuccinimide. It is stable and easily handled, and it slowly gets decomposed in water to give .In bromohydrin formation, a bromonium ion intermediate is formed.

02

The product expected from the reaction of cyclopentene with NBS and water

The formation of bromohydrin takes place when the solvent used is DMSO and the reagent used is NBS.

When cyclopentene is reacted with NBS and water, it forms bromohydrin, where Br and OH groups are trans to each other.

Product formation

The stereochemistry of the product is,

Stereochemistry of the product.

There is an anti addition where an OH is present below the plane and Br is present above the plane.

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Most popular questions from this chapter

Iodine azide,adds to alkenes by an electrophilic mechanism similar to that of bromine. If a monosubstituted alkene such as1-butene isused, only one product results:

b) Calculate formal charges for the atoms in both resonance structuresyou drew for,in part (a).

From what alkenes might the following alcohols have been prepared?

b)

Predict the products of the following reactions (the aromatic ring is

unreactive in all cases). Indicate regiochemistry when relevant.

Iodine azide,, adds to alkenes by an electrophilic mechanism similar to that of bromine. If a monosubstituted alkene such as 1-butene is used, only one product results:

c)

In light of the result observed when,adds to 1-butene, what is

the polarity of thebond? Propose a mechanism for the reaction

using curved arrows to show the electron flow in each step.

Show the structures of alkenes that give the following products on oxidative cleavage with in acidic solution

d.CHC3H2C=OCH2CH2CH2CH2CO2H
See all solutions

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