Consider the molecule 1,3-dimethyl-1,2,3,4-te | vedclass

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(C) The basicity of nitrogen atoms depends on the availability of the lone pair. In $1,3-dimethyl-1,2,3,4-tetrahydroquinoxaline$,the amino group at th

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Structure with protonation at the $N-3$ position (tertiary amine).

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(C) The basicity of nitrogen atoms depends on the availability of the lone pair. In $1,3-dimethyl-1,2,3,4-tetrahydroquinoxaline$,the amino group at the $5$-position is conjugated with the benzene ring,reducing its basicity. The nitrogen at the $1$-position is an aniline-like nitrogen (conjugated with the ring),while the nitrogen at the $3$-position is an aliphatic tertiary amine. Aliphatic amines are more basic than aromatic/conjugated amines. Therefore,the nitrogen at the $3$-position is the most basic and will be protonated first to form the stable conjugate acid.

Consider the molecule $1,3-dimethyl-1,2,3,4-tetrahydroquinoxaline$ with an amino group at the $5$-position. Upon protonation,which nitrogen atom is the most basic and will be protonated first? Identify the correct structure of the product '$A$' formed after protonation.

Similar Questions

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