Starting with a Primary Alkyl Bromide, Which of the Following

Multiple Choice

Starting with a primary alkyl bromide, which of the following results in an overall decrease in the length of the carbon skeleton by one carbon?

A) substitute bromide with acetylide, then cleave the triple bond
B) substitute bromide with acetylide, then reduce the alkyne to an alkene
C) substitute bromide with methoxide
D) eliminate hydrogen bromide to produce an alkene, then cleave the double bond