Consider the reaction of N,N-dimethylaniline with nitrous acid at 0-5 degrees Celsius. What is the major product formed?

A. p -Nitroso-N,N-dimethylaniline — Tertiary aromatic amines undergo electrophilic aromatic substitution with the nitrosonium ion at the para position.

JEE Main · ChemistryHard

$Consider the reaction of C_{6} H_{5} N (CH_{3})_{2} with HNO_{2} at 0 - 5^{\circ} C . What is the major product formed?$

A. $p -Nitroso-N,N-dimethylaniline$
B. $N -Nitroso-N-methylaniline$
C. $C_{6} H_{5} N_{2}^{+} Cl^{-}$
D. $N,N-Dimethyl-p-nitroaniline$

Show correct answer & step-by-step solution

Correct answer: A — $p -Nitroso-N,N-dimethylaniline$

Solution

$The reaction of HNO_{2} with HCl generates the electrophile NO^{+} .$
$Tertiary aromatic amines like C_{6} H_{5} N (CH_{3})_{2} are highly activated toward electrophilic aromatic substitution.$
$The NO^{+} ion attacks the para position due to the strong ortho/para directing effect of the dimethylamino group.$
$Hence the answer is (A).$

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Consider the reaction of C6​H5​N(CH3​)2​ with HNO2​ at 0−5∘C. What is the major product formed?

Solution

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$Consider the reaction of C_{6} H_{5} N (CH_{3})_{2} with HNO_{2} at 0 - 5^{\circ} C . What is the major product formed?$