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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–enol 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

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

Let be a group and assume that for each positive integer i , Ni is a normal subgroup of G. If every element of can be written uniquely in the form ni1 .ni2 ...nikwith i1 < i2 < ... < ik and nij∈Nij , prove that G≅∑i=1 Ni (see Exercise 34). [Hint: Adapt the proof of Theorem 9.1 by defining f(a1, a2...) to be the product of those ai that are not the identity element.]

What products would you expect from the following reactions?

a. CH3CH2CH2C≡CH+Cl2

How would you carry out the following reactions to introduce deuterium into organic molecules?

(a)

b.

c.

d.

Each of the following syntheses requires more than one step. How

would you carry them out?

(a)

(b)

See all solutions

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