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Chapter 6: Q50P (page 330)

Give a mechanism to explain the two products formed in the following reaction.

Short Answer

Expert verified

The mechanism of the given reaction is as follows,

Step by step solution

01

Concept

The bromination reaction is the process by which one or more bromine atoms are added to a chemical. Halogination reaction includes bromination reactions. N-bromosuccinimide, also known as NBS (sourse of Br), is employed in this reaction as a reagent to aid in radical substitution.

A free radical is a molecule that lacks charge and has an unpaired electron. Free radicals are extremely reactive substances with a brief shelf life.

02

Explain the mechanism

  1. First, the reagent N-bromosuccinimide (NBS) that produces the bromine radical Br undergoes radical formation.

2. In the second step, the 3-methylbut-1-ene reacts with the benzylic free radical to form tertiary allylic free radical.

3. In the third step, the tertiary allylic free radical is gives the reasonance structure of primary allylic free radical,

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Most popular questions from this chapter

Question: Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.

d)

For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.

(a) ethyl chloride or ethyl iodide

(b) 1-bromopropane or cyclopropane

(c) cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-ene

(d) cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutane.

Question: For each of the following compounds,

  1. give the IUPAC name.
  2. give the common name (if possible).
  3. classify the compound as a methyl, primary, secondary, or tertiary halide.

a)

b)

c)

d)

e)

f)

Strawberry growers have used large quantities of methyl bromide (b.p. 4掳C) to sterilize the soil before planting their crops. Like some of the freons, methyl bromide can diffuse up into the stratosphere, where it damages the protective ozone layer. Agricultural chemists have suggested using methyl iodide (b.p. 43掳C) as a replacement for methyl bromide. Why is methyl iodide likely to be more toxic to agricultural pests (and people) than methyl bromide? Why is methyl iodide less likely to reach the stratosphere than methyl bromide?

Kepone, aldrin, and chlordane are synthesized from hexachlorocyclopentadiene and other five-membered ring compounds. Show how these three pesticides are composed of two five-membered rings.
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