Question

When (R)-3-bromo-2,3-dimethylpentane is treated with sodium hydroxide, four different alkenes are formed.
Draw all four products and rank them in order of increasing stability.

Answer 1

How would i choose which hydrogens will undergo a proton transfer? I figured few products but i am not sure if the procedure i am doing is correct.

Answer 2

Simply, i am looking over the hydrogens that are capable of creating a double bond when its protons gets transferred.

Answer 3

Do i need to draw the newman projections to see which hydrogens creates an antiperiplanar with the bromide ? If they are adjacent, then that hydrogen is the one getting transferred.

Answer 4

@Photon336

Answer 5

I am just going by the hydrogens that its electrons can create a double bond.

Answer 6

The four products would be