Which order of reactions would most effectively convert trans-2-butene into 1-butene?
A) convert to the gem-dibromoalkane, then to the terminal alkyne, then to the terminal alkene
B) convert to an alcohol, then to a terminal alkyne, finally to the terminal alkene
C) convert to the terminal alkene in one step
D) shorten the chain by two carbons, then add a two-carbon alkene to the end
E) convert to an alkane, then to a terminal alkyne, and finally to a terminal alkene

Question

Quizplus · Accepted Answer

Converting trans-2-butene to the gem-dibromoalkane will allow for elimination of HBr to form the terminal alkyne. The terminal alkyne can then be reduced to the terminal alkene using a variety of methods. This sequence of reactions is known as the Corey-Fuchs reaction and is commonly used for converting disubstituted olefins to terminal olefins.

Which Order of Reactions Would Most Effectively Convert Trans-2-Butene into 1-Butene