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Chapter 9: Q9-7P a (page 272)

How would you prepare the following carbonyl compounds starting from an alkyne (reddish brown Br)?

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01

Hydroboration – oxidation reaction

The hydroboration–oxidation to the direct, mercury(II)-catalyzed hydration reaction. Direct hydration with aqueous acid and mercury(II) sulfate leads to a methyl ketone,

02

 Formation of compound a

Terminal alkyne undergoes two additions, giving a doubly hydroborated intermediate.

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Most popular questions from this chapter

Synthesize the following compounds using 1-butyne as the only source of carbon along with any inorganic reagents you need. More than one step may be needed.(a) 1,1,2,2- Tetrachlorobutane(b) 1,1- Dichloro-2-ethylcyclopropane

Question: Identify the reagents a–c in the following scheme:

Question: How would you carry out the following conversions? More than one

step may be needed in some instances.

Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.

b.(CH3)2CHC≡CCH2CH3

A cumulene is a compound with three adjacent double bonds. Draw an orbital picture of a cumulene. What kind of hybridization do the two central carbon atoms have? What is the geometric relationship of the substituents on one end to the substituents on the other end? What kind of isomerism is possible? Make a model to help see the answer.

R2C=C=C=CR2

A cumulene
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