Organic Chemistry Synthesis

Question

Use the following starting material and any other non organic materials to create the target molecule. Pay attention to having a green synthesis.

Starting material: 3-methyl hex-1-yne

Target molecule: 3-bromo 3 methyl hexane

Answer 1

The transformation you're describing can be accomplished in two steps. The first reaction will be with one equivalent of HBr. This will be an addition reaction where the hydrogen will be added to the terminal position of the alkyne to form the more stable secondary carbocation. This species will undergo a hydride transfer rearrangement to form the even more stable tertiary carbocation. The bromide anion will them come and attack the carbocation to form 3-bromo-3-methylhex-1-ene. This alkene can then be reduced to the alkane in a second reaction using hydrogen gas and palladium on carbon.