03. Synthesis of a Bulky Alkyne

This is a challenging synthesis as it pushes students towards the incorrect solution if they are not paying attention to the limitations of their reactions.

The key here is to recognize that it’s impossible to do the SN2 reaction using the alkynide ion with a tertiary alkyl halide. So, we’ll have to find the alternative synthetic strategy. The alternative strategy I propose here involves making a new carbon-carbon bond using the Grignard reaction and then reconstructing our triple bond anew.