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

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

Question

(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

Vedclass · Accepted Answer

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

Vedclass · Answer

(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

The major product $(R)$ of the following reaction is:
Aniline $\xrightarrow[{pyridine}]{{CH_3COCl}}$ $P$ $\xrightarrow[{CH_3COOH}]{{Br_2}}$ $Q$ $\xrightarrow{{{H_3O^{+}}}}$ $R$

In the reaction $CH_3NH_2 + X + KOH \rightarrow CH_3NC + 3KCl + 3H_2O$,what is $X$?

What is the product formed when acetamide reacts with $NaOBr$ in an alkaline medium?

Which one of the following is the most basic compound?

In the given reaction,$[X]$ is:
$4-\text{nitrostyrene} \xrightarrow{[X]} 4-\text{ethylaniline}$

Vedclass Test Series

Exam Paper Generator

Online Exam Module