Roberts discovered the nucleophilic aromatic substitution of chlorobenzene with an amino group has an intermediate with this functional group.
In the presence of a strong base and 1,3-diaminopropane, this functional group moves to the end of an unbranched chain. A two-step reaction that produces these compounds starts with a one carbon homologation of an aldehyde to a dibromoolefin, then treats it with an alkyllithium reagent. Roberts discovered the nucleophilic aromatic substitution of chlorobenzene with an amino group has an intermediate with this functional group. Hydrogens attached to them have a pKa of about 25. This functional group is synthesized in the Corey-Fuchs reaction. For 10 points, identify this functional group, which can be partially hydrogenated to an alkene via Lindlar's catalyst and contains a carbon-carbon triple bond.
In the presence of a strong base and 1,3-diaminopropane, this functional group moves to the end of an unbranched chain.
alkyne [prompt on acetylene]