Predict the reagents or products $(1)$ to $(5)$ in the following reaction sequence:
$p-Nitrotoluene$ $\xrightarrow{(1)} p-Toluidine$ $\xrightarrow{(CH_3CO)_2O/\text{Pyridine}} p-Acetotoluidide$ $\xrightarrow{HNO_3/H_2SO_4} (2)$ $\xrightarrow{(3)} (4)$ $\xrightarrow{(5)} 3-Nitrotoluene$

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(A) The reaction sequence is as follows:
$(1)$ Reduction of $p-nitrotoluene$ to $p-toluidine$ is carried out using $Sn/HCl$.
$(2)$ Nitration of $p-acetotoluidide$ gives $2-nitro-4-methylacetanilide$ (or $4-acetamido-3-nitrotoluene$).
$(3)$ Hydrolysis of the acetamido group using $H_2O/H^+$ gives $4-amino-3-nitrotoluene$.
$(4)$ Diazotization of $4-amino-3-nitrotoluene$ using $NaNO_2/HCl$ at $0-5^{\circ}C$ gives $3-nitro-4-methylbenzenediazonium$ chloride.
$(5)$ Reduction of the diazonium salt using $H_3PO_2/H_2O$ gives $3-nitrotoluene$.

Explore More

Similar Questions

$C_6H_5CH_2Cl$ $\xrightarrow{\text{Alc. } NH_3} A$ $\xrightarrow{2 CH_3Cl} B$. The product $B$ is

$X$ and $Y$ (major products) in the following reaction sequence are:

Which of the following compounds is more basic than aniline?

Which of the following statements is incorrect for primary amines?

Difficult
View Solution

Nitrosobenzene can be prepared by oxidizing aniline with which of the following reagents?

Difficult
View Solution

Vedclass Products

For Students

Vedclass Test Series

Mock tests in real JEE/NEET style with performance analysis. 5-day free trial.

Start Free Trial
For Teachers

Exam Paper Generator

Generate Set A/B/C/D exam papers from 7.5L+ questions in 2 minutes. 3 chapters free.

Try Free
For Institutes

Online Exam Module

Live online exams with unlimited students, 360° analytics & white-label branding.

See Demo