Here's a diagram of the reaction:
CH₂NH₂ + TsOH -> [CH₂NH₂H⁺] + TsO⁻
[CH₂NH₂H⁺] -> CH₂NH⁺ + H₂O
CH₂NH⁺ + TsO⁻ -> C₆H₅NH₂⁺TsO⁻
C₆H₅NH₂⁺TsO⁻ -> C₆H₅SO₂NH₂ + TsOH
What is the major product?
The major product of the reaction CH₂NH₂ + TsOH is benzenesulfonamide (C₆H₅SO₂NH₂):
Reaction:
CH₂NH₂ + TsOH → C₆H₅SO₂NH₂ + H₂O
Step-by-step explanation:
TsOH (p-toluenesulfonic acid) acts as a catalyst in this reaction. It protonates the amine group on methylamine (CH₂NH₂) to make it a better leaving group.
The protonated methylamine then loses water, forming a reactive intermediate called a nitrenium ion (CH₂NH⁺).
The nitrenium ion attacks the benzene ring of the tosyl group (TsOH), displacing the tosylate group (OTs).
The resulting intermediate then loses a proton to form the final product, benzenesulfonamide.
This reaction is an example of electrophilic aromatic substitution.
The product, benzenesulfonamide, is a useful intermediate in the synthesis of many pharmaceuticals and other organic compounds.