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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: Why is compound X formed in the following reaction instead of its constitutional isomer Y?

Question: Draw the enol tautomer of (a) and the keto tautomer of (b).

a.

b.

Question: Draw a stepwise mechanism for the following reaction.

Question: Draw the products formed when the following alkynes are treated with each set of reagents: [1] H2O,H2SO4,HgSO4;[2]R2BHfollowedbyH2O2,OH-.

a.

b.

Question: Devise a synthesis of CH3CH2C≡CCH2CH2OHfromCH3CH2OHas the only organic starting material. You may use any other needed reagents.
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