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

Question

Quizplus · Accepted Answer

Eliminating hydrogen bromide to form an alkene and then cleaving the double bond (e.g., via ozonolysis) can result in the shortening of the carbon chain by one carbon.

Starting with a Primary Alkyl Bromide, Which of the Following