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Chapter 16: PROBLEM 16.41 (page 635)

Question: Draw the products formed when each compound is treated with one equivalent of HBr.

a.

b.

c.

Short Answer

Expert verified

a.

b.

c.

Step by step solution

01

Addition of HBr

The addition of HBr takes place via the “carbocation formation.”

02

1,2 and 1,4 addition

During the addition of HBr, two carbocationic intermediates form as part of the reaction.

03

Products of given reactions

a. The double bonds are not conjugated. Hence, the addition of HBr leads to the formation of only one addition product.

Product of a

b.The given diene is conjugated. Hence, the addition of the strong acid HBr leads to the formation of two products, i.e., 1,2 and 1,4 addition products.

The addition products of the reaction are:

Products of bc. The given diene is conjugated. Hence, the addition of the strong acid HBr leads to the formation of two products, i.e., 1,2 and 1,4 addition products.

The addition products of the reaction are:

Products of c

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Most popular questions from this chapter

Question: Addition of HBr to alleneCH2=C=CH2forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.

Question: The following reactions have been used to synthesize dieldrin and aldrin (named for Diels and Alder), two pesticides having a similar story to DDT (Section 7.4). Identify the lettered compounds in this reaction scheme.

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

Question: Devise a stepwise synthesis of each compound from dicyclopentadiene using a Diels–Alder reaction as one step. You may also use organic compounds having ≤ 4 C’s, and any required organic or inorganic reagents:

a.

b.

c.

Question: What diene and dienophile are needed to prepare each compound by a Diels-Alder reaction?

a.

b.
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