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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 a second resonance structure and the hybrid for each species, and then rank the two resonance structures and the hybrid in order of increasing stability

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Question:Draw all reasonable resonance structures for acetic anhydride

Question: Compounds containing triple bonds are also Diels鈥揂lder dienophiles. With this in mind, draw the products of each reaction.

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Question: Draw the product of each Diels鈥揂lder reaction.

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Question: Draw the structure of each compound

  1. (Z)-penta-1,3-diene in the s-trans conformation
  2. (2E,4Z)-1-bromo-3-methylhexa-2,4-diene
  3. (2E,4E,6E)-octa-2,4,6-triene
  4. (2E,4E)-3-methylhexa-2,4-diene in the s-cis conformation
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