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Chapter 26: Q19P (page 1049)

What product is formed by ring-closing metathesis of each compound?

a.

b.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Metathesis reaction

There are several classes of metathesis reactions, and some of them are ring-opening metathesis reactions and ring-closing metathesis reactions. The pharmaceutical industry utilizes metathesis reactions for synthesizing drugs.

02

Ring-closing metathesis reaction

Ring-closing metathesis reactions occur with the help of a Grubbs catalyst. Several alkenes are acquired as products in metathesis reactions.

03

Starting material needed to synthesize the given compounds

a. The given diene reacts with a Grubbs catalyst to form the ring-closing metathesis product. The reaction can be given as follows.

Product formed by the ring-closing metathesis of compound a

b. The reaction of the given compound with a Grubbs catalyst gives rise to the ring-closing metathesis product. The reaction can be given as follows.

Product formed by the ring-closing metathesis of compound b

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Most popular questions from this chapter

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 “expected” coupling product F with the phenyl group bonded directly to the carbon–carbon 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 products formed when each alkene is treated with Grubbs catalyst.

a.

b.

c.

Devise a synthesis of the given trans vinylborane, which can be used for bombykol synthesis (Figure 26.1). All of the carbon atoms in the vinylborane must come from acetylene, nonane-1,9-diol, and catecholborane.

Although diazomethane ( CH2N2) is often not a useful reagent for preparing cyclopropanes,other diazo compounds give good yields of more complex cyclopropanes. Draw a stepwisemechanism for the conversion of diazo compound A to B, an intermediate in the synthesis ofsirenin, the sperm attractant produced by the female gametes of the water mold Allomyces.

Devise a synthesis of (E)-1-phenylhex-1-ene ( CH3CH2CH2CH2CH=CHPh) using hydrocarbons having ≤ 6 C’s and a Suzuki reaction as one of the steps.
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