Chapter 26: Q 21. (page 1069)
What organic halide is needed to convert lithium divinylcuprate to each compound?
a.
b.
c.
Short Answer
Answer
a.
b.
c.
Chapter 26: Q 21. (page 1069)
What organic halide is needed to convert lithium divinylcuprate to each compound?
a.
b.
c.
Answer
a.
b.
c.
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Get started for freeWhat starting material is needed to prepare each compound by a ring-closing metathesis reaction?
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 โexpectedโ coupling product F with the phenyl group bonded directly to the carbonโcarbon 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?
Many variations of ring-closing metathesis have now been reported. Tandem ring-openingโ ring-closing metathesis can occur with cyclic alkenes that contain two additional carbonโ carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a DielsโAlder reaction with diethyl maleate as the dienophile.
a.
b.
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.
Treatment of cyclohexene with and Zn(Cu) forms two stereoisomers of molecular formula . Draw their structures and explain why two compounds are formed.
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