An Unknown Compound with the Molecular Formula C₁₅H₂₃N Is Treated

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The Answer is The conditions indicate a Hofmann elimination occurred. Recall that the first step of the Hofmann elimination is alkylation of an amine to form a good leaving group. In the second step, the Ag₂O acts as a base to drive an E2 elimination and form an alkene. Working backward, the amine must have been bonded to one of the alkene carbons, and the methyl group on the amine came from the CH₃I.

The conditions indicate a Hofmann elimination occurred. Recall that the first step of the Hofmann elimination is alkylation of an amine to form a good leaving group. In the second step, the Ag<sub>2</sub>O acts as a base to drive an E2 elimination and form an alkene. Working backward, the amine must have been bonded to one of the alkene carbons, and the methyl group on the amine came from the CH<sub>3</sub>I. Note that option A has two possible beta hydrogens that can be removed. Elimination of the tertiary proton will give the products indicated, but the major product will be removal of the secondary proton, since it forms the less stable disubstituted alkene. Option B has only one possible beta hydrogen and the elimination will give the desired product. Therefore, option B must have been the unknown compound.

Note that option A has two possible beta hydrogens that can be removed. Elimination of the tertiary proton will give the products indicated, but the major product will be removal of the secondary proton, since it forms the less stable disubstituted alkene. Option B has only one possible beta hydrogen and the elimination will give the desired product. Therefore, option B must have been the unknown compound.

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An Unknown Compound with the Molecular Formula C₁₅H₂₃N Is Treated

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