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Chapter 16: PROBLEM 16.44 (page 635)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

Mechanism for the formation of products

Step by step solution

01

Radical formation

The reagent ROOR undergoes homolytic fission to form two radical species.

02

Nature of HBr

HBr behaves opposite to its normal nature of attacking the carbon in the C=C with fewer hydrogen atoms. In the presence of radical species, the ion adds to the carbon with more hydrogen atoms.

03

Products of given reactions

ROOR undergoes homolytic fission to form its two radical fragments.

The radicals attack the HBr and thus form radicals. These radicals attack the diene to form two new radicals giving two products. The products and mechanism of the reaction are shown hereunder:

Now, the two radical structures react with HBr as:

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Most popular questions from this chapter

Question. Draw all possible resonance structures for the following cation and indicate which structure makes the largest contribution to the resonance hybrid.

Question: What diene and dienophile are needed to prepare each Diels–Alder product?

a.

b.

c.

d.

Question: Explain why the cyclopentadienide anion A gives only one signal in its 13C NMR spectrum.

Question: Ignoring stereoisomers, draw all products that form by addition of HBr to (E)-hexa-1,3,5-triene.

Question: Use resonance theory explains why the labeled C-O bond lengths are equal in the acetate ion.
See all solutions

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