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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

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: Show the products you expect when each compound reacts with NBS with light shining on the reaction.

d)

Triethyloxonium tetrafluoroborate, (CH3CH2)3O+ BF4−, is a solid with melting point 91–92°C. Show how this reagent can transfer an ethyl group to a nucleophile (Nuc:−) in an SN2 reaction. What is the leaving group? Why might this reagent be preferred to using an ethyl halide? (Consult Table 6-2.)

Predict the compound in each pair that will undergo the SN2 reaction faster.

(a.)

(b.)

(c.)

(d.)

(e.)

(f.)

Draw the structures of the following compounds.

(a)sec-butyl bromide

(b)isobutyl chloride

(c) 1,2-chloro-3-methylpentane

(d) 2,2,2-tribromoethanol

(e) trans-1-bromo-2-methylcyclohexane

(f) methylene bromide

(g) iodoform

(h) 1-bromo-1-isopropylcyclopentane

(i) tert-pentyl bromide
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