Question

How would you draw the skeletal structure of the product you would expect to result from the following reaction?

Answer 1

See below.

Explanation:

This is a reaction of nitrous acid with a secondary amine.

Nitrous acid is unstable and is always prepared immediately before use by reacting sodium nitrite in the cold with a strong acid like `"HCl"`.

Nitrous acid is a weak acid, so you get the reaction:

`"H"_3"O"^+ + "NO"_2^"-" → "H"_2"O" + "HNO"_2`

The nitrous acid reacts with a secondary amine to form a nitrosamine:

`underbrace("R"_2"NH")_color(red)("a secondary amine") + "HNO"_2 stackrelcolor(blue)("0 °C"color(white)(m))(→) underbrace("R"_2"N-N=O")_color(red)("a nitrosamine") + "H"_2"O"`

Your compound is a secondary amine. The structure of the product is therefore

Nitrosamines are insoluble yellow oils.

They are powerful carcinogens — Be extremely careful when handling them!