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Why is it generally impossible to separate the individual enantiomers of simple chiral aliphatic terAmines Chemistry Question

Question

Why is it generally impossible to separate the individual enantiomers of simple chiral aliphatic tertiary amines (like ethylmethylpropylamine) at room temperature?

Answer: B

💡 Solution & Explanation

Tertiary amines with three different alkyl groups possess a chiral nitrogen center. However, they undergo a rapid oscillation called nitrogen inversion (the umbrella effect) through a planar $sp^2$ transition state at room temperature. This interconverts the enantiomers too quickly for them to be isolated or resolved.

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