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Chapter 9: Q9-5P (page 270)

What alkynes would you start with to prepare the following ketones?

Short Answer

Expert verified

Answer:

a.

b.

Step by step solution

01

Hydration of alkynes

Alkyneundergo hydration in the presence of mercury(II) sulfate. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H attaches to the less highly substituted one.

Enol is an intermediate in the reaction, which rearranges into a ketone by a process called keto鈥揺nol tautomerism. The individual keto and enol forms are said to be tautomers.

02

Formation of ketone(a) from alkyne

The formation of the single product shows alkyne is symmetrical.

The reaction occurs with Markovnikov regiochemistry. Enol is an intermediate in the reaction, which rearranges into a ketone by a process called keto-enol tautomerism.

03

Formation of ketone(b) from alkyne

The formation of the two products shows alkyne is unsymmetrical.

The reaction occurs with Markovnikov regiochemistry. Enol is an intermediate in the reaction, which rearranges into a ketone by a process called keto-enol tautomerism

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Most popular questions from this chapter

Question: Identify the reagents a鈥揷 in the following scheme:

Terminal alkynes react with and water to yield bromo ketones. For example:

Propose a mechanism for the reaction. To what reaction of alkenes is

the process analogous?

Using any alkyne needed, how would you prepare the following alkenes?

(c) 3-Methyl-1-pentene

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

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鈮�CCH2CH3
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