Show how the following synthetic transformation can be accomplished. Give the structures of all intermediates.
2,2-dibromopentane → pent-2-yne

Synthetic transformation of 2,2-dibromopentane to pent-2-yne with HBr.

Synthetic transformation of 2,2-dibromopentane to pent-2-yne with H2SO4.

Synthetic transformation of 2,2-dibromopentane to pent-2-yne with NaNH2.

Synthetic transformation of 2,2-dibromopentane to pent-2-yne with KOH.

Show how the following synthetic transformation can be accomplished. Give the structures of all intermediates.2,2-dibromopentane → pent-2-yne