Alkyne acidity and carbon carbon bond formation

Abstract

This activity introduces student to the effects of hybridization of carbon atoms on the acidity (pKa value) of the C-H bond.  The activity then discusses how the acetylide ion can be used as an effective nucleophile in SN2 reactions with methyl and primary substrates.  Upon completion of this activity students should understand relative acidity of C-H bonds on carbons with different hybridizations and demonstrate how to form and use acetylide ions as nucleophiles in SN2 reactions.

Level: Undergraduate

Setting: Classroom

Activity Type: Learning Cycle

Discipline: Chemistry

Course: Organic chemistry

Keywords: alkynes, SN2, substitution, acid/base, acetylide ions, nucleophile, pKa