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Chapter 22: Problem 541

Predict the products expected in the reactions of the following amines with nitrous acid (prepared from \(\mathrm{NaNO}_{2}+\mathrm{HCl}\) in aqueous solution):

Short Answer

Expert verified
To predict the products expected in the reactions of amines with nitrous acid, first identify the type of amine (primary, secondary, or tertiary). Primary amines form diazonium salts (\(R-N_{2}^{+}X^{-}\)), secondary amines form N-nitrosoamines (\(R_{2}-N-NO\)), and tertiary amines form nitrosoamines (\(R_{3}N-NO^{+}X^{-}\)).

Step by step solution

01

Identify the type of amine

Determine whether the amine is primary, secondary, or tertiary. Primary amines have one alkyl group attached to the nitrogen atom, secondary amines have two alkyl groups attached to the nitrogen atom, and tertiary amines have three alkyl groups attached to the nitrogen atom.
02

Reaction of primary amines with nitrous acid

If the given amine is primary, it will react with nitrous acid to form a diazonium salt. The reaction is as follows: \[R-NH_{2} + HNO_{2} \rightarrow R-N_{2}^{+}X^{-} + H_{2}O\] Where R is an alkyl group and X is the counter-ion (in this case, Cl-).
03

Reaction of secondary amines with nitrous acid

If the given amine is secondary, it will react with nitrous acid to form an N-nitrosoamine. The reaction is as follows: \[R_{2}NH + HNO_{2} \rightarrow R_{2}-N-NO + H_{2}O\] Where R is an alkyl group.
04

Reaction of tertiary amines with nitrous acid

If the given amine is tertiary, it will react with nitrous acid to form a nitrosoamine. The reaction is as follows: \[R_{3}N + HNO_{2} \rightarrow R_{3}N-NO^{+}X^{-}\] Where R is an alkyl group and X is the counter-ion (in this case, Cl-). Follow these steps based on the type of amine reactant provided to predict the product(s) expected from the reaction of the amine with nitrous acid.

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