Chapter 26: Q 17. (page 1067)
What starting material is needed to synthesize each compound by a ring-closing metathesis reaction?
a.

b.

c.

Short Answer
Answer
a.

b.

c.

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Chapter 26: Q 17. (page 1067)
What starting material is needed to synthesize each compound by a ring-closing metathesis reaction?
a.

b.

c.

Answer
a.

b.

c.

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The reaction of cyclohexene with iodo-benzene under Heck conditions forms E, a coupling product with the new phenyl group on the allylic carbon, but none of the 鈥渆xpected鈥 coupling product F with the phenyl group bonded directly to the carbon鈥揷arbon double bond.
a. Draw a stepwise mechanism that illustrates how E is formed.
b. Step [2] in Mechanism 26.2 proceeds with syn addition of Pd and R' to the double bond.What does the formation of E suggest about the stereochemistry of the elimination reaction depicted in Step [3] of Mechanism 26.2?

Draw the product formed from the ring-closing metathesis of each compound. Then, devisea synthesis of each metathesis starting material using any of the following compounds: , alcohols with less than five carbons, and any needed organic and inorganicreagents.
a.

b.

What product is formed in the Suzuki coupling of A and B? This reaction was a key step in the synthesis of losartan, a drug used to treat hypertension.

Draw the products formed when each alkene is treated with Grubbs catalyst.
a.

b.

c.

Devise a synthesis of each substituted cyclopropane. Use acetylene , as a startingmaterial in part (a), and cyclohexanone as a starting material in part (b). You may use anyother organic compounds and any needed reagents.
a.

b.

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