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

Identify the products $y$ and $x$ in the following reaction sequence:
$C_6H_5CONH_2 \xrightarrow{NaOBr} y$
$C_6H_5CONH_2 \xrightarrow[(ii) H_3O^+]{(i) C_6H_5SO_2Cl / py, \Delta} x$

Which among the following decreasing order of boiling points is correct for amines?

The diazonium salt of which of the following compounds will form a coloured dye on reaction with $\beta$-Naphthol in $NaOH$?

In the following compounds,the order of basicity is as follows:

Why is benzene diazonium chloride not stored and is used immediately after its preparation?

Vedclass Test Series

Exam Paper Generator

Online Exam Module