# Will 2-methylbutanal undergo aldol condensation

Will 2-methylbutanal undergo aldol condensation?

We are taught that it will not because the +I effect makes the carbanion unstable, but if we make an enolate ion, isn't it resonance stabilized by the C=O group?

There is no reason why the aldehyde cannot undergo an aldol reaction with itself. Enolates are not rendered unstable by the presence of additional alkyl substituents; in fact they are considered to be more stable. (See: formation of silyl enol ethers with $\ce{Et3N}$/$\ce{Me3SiCl}$.)
However, there is no way it can eliminate $\ce{H2O}$ to form the α,β-unsaturated ketone, since the aldol product does not have any α-hydrogens. Strictly you cannot call it an aldol condensation, although often no distinction is made in the literature between an aldol addition and a condensation.