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The compound 2,6-dimethyl-N,N-dimethylaniline is a substantially stronger base than simple N,N-dimetAmines Chemistry Question

Question

The compound 2,6-dimethyl-N,N-dimethylaniline is a substantially stronger base than simple N,N-dimethylaniline. What phenomenon causes this?

Answer: B

💡 Solution & Explanation

Severe steric clash between the ortho methyl groups and the N-methyl groups forces the bulky $-N(CH_3)_2$ moiety to twist completely out of the benzene ring's plane (Steric Inhibition of Resonance). This prevents lone pair delocalization, heavily localizing electron density on nitrogen.

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