Chapter 26: Q 40. (page 1072)
Devise a synthesis of diene A from (Z)-2-bromostyrene as the only organic starting material. Use a Suzuki reaction in one step of the synthesis.

Short Answer
Answer
Synthesis of compound A
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Chapter 26: Q 40. (page 1072)
Devise a synthesis of diene A from (Z)-2-bromostyrene as the only organic starting material. Use a Suzuki reaction in one step of the synthesis.

Answer
Synthesis of compound A
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Draw the product formed from ring-closing metathesis of each compound.
a.

b.

Draw the coupling product formed when each pair of compounds is treated with , , and .

What starting material is needed to prepare each compound by a ring-closing metathesis reaction?

One step in the synthesis of the nonsteroidal anti-inflammatory drug rofecoxib (trade name Vioxx) involves Suzuki coupling of A and B. What product is formed in this reaction?

In addition to using and base to synthesize dihalocarbenes (Section 26.4), dichlorocarbene can be prepared by heating sodium trichloroacetate. Draw a stepwise mechanism for this reaction.
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