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Chapter 11: 5P (page 426)

Convert each compound to hex-1-yne,

a.b.

c.

Short Answer

Expert verified

a.

b.

c.

.

Step by step solution

01

Preparation of alkyne from geminal dihalide

Geminal dihalides are treated with a strong base to remove the halides and hydrogens to form alkyne. The pathway of the elimination reaction is E2.The general reaction scheme is given below:

02

Conversion of the compounds to hex-1-yne

a.The given compound is a dihalide and thus can directly be converted to an alkyne upon treatment with 2 equivalent . The reaction is shown below:

Conversion of geminal halide to alkyne

b.

The given compound has one halide attached to the alkene group and can directly be converted to alkyne using one equivalent .

c.

The given compound is a simple alkene and has to be converted to a dihalide by treating it with chloride. It is further converted to alkyne using a similar reagent.

Alkyne formation

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Most popular questions from this chapter

Question: What reagents are needed to convert(CH3CH2)3C鈮�CHto each compound?


a.


b.


c.

d.

Question: Devise a synthesis of CH3CH2CH2CHO from two-carbon starting materials.

Question: How is each compound related to A? Choose from tautomers, constitutional isomers but not tautomers, or neither


A.

Question: Tautomerization in base resembles tautomerization in acid, but deprotonation precedes protonation in the two-step mechanism. (a) Draw a stepwise mechanism for the following tautomerization. (b) Then, draw a stepwise mechanism for the reverse reaction, the conversion of the keto form to the enol.

Question:

(a) Draw two different enol tautomers of 2-methylcyclohexanone.

(b) Draw two constitutional isomers that are not tautomers, but contain a C=C and an O-H group.

2-methylcyclohexanone
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