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The highlighted bond joins a nitrile carbon atom to an alkyne carbon atom. The
nitrile carbon atom, being joined to a nitrogen atom via a carbon-nitrogen triple
bond, can only be joined to one additional atom. Therefore, this atom is sp hybri-
dized. Additionally, the alkyne carbon is joined to the nitrile carbon and a second
alkyne carbon atom. Because the two alkyne carbon atoms are joined by a triple
bond, there can be no more than two atoms bound to the highlighted alkyne
carbon. Therefore, because the alkyne carbon is bound to two separate atoms, this
carbon is sp hybridized. Based on the atomic hybridizations, the nitrile carbon is con-
nected to its bound atoms in a linear geometry, and the alkyne carbon is connected to
its bound atoms in a linear geometry.
The highlighted bond joins two methyl carbon atoms. Each methyl carbon is joined
to a methyl carbon and three hydrogen atoms. Therefore, because each methyl
carbon is bound to four separate atoms, they are sp 3 hybridized. Based on the
atomic hybridizations, each methyl carbon is connected to its bound atoms in tetra-
hedral geometries.
The highlighted bond joins a nitrile carbon atom to an amine nitrogen atom. The
nitrile carbon atom, being joined to a nitrogen atom via a carbon-nitrogen triple
bond, can only be joined to one additional atom. Therefore, this atom is sp hybri-
dized. However, the amine nitrogen is joined to the nitrile carbon and two hydrogen
atoms. Additionally, the amine nitrogen possesses one lone electron pair. Therefore,
because the amine nitrogen is bound to three separate atoms and possesses one lone
electron pair, this nitrogen is sp 3 hybridized. Based on the atomic hybridizations, the
nitrile carbon is connected to its bound atoms in a linear geometry, and the amine
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