Question

Convert each compound to hex-1-yne,

a.b.

c.

Short answer

a.

b.

c.

.

Step-by-step solution

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:

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