57E - Organic Chemistry (Mcmurry)

Question

All attempts to isolate primary and secondary nitroso compounds result solely in the formation of oximes. Tertiary nitroso compounds, however, are stable. Explain.

Step-by-Step Solution

Answer

The tertiary nitroso compound is stable due to the lack of hydrogen atoms and isomerisation.

Step 1: Primary or secondary nitroso compounds

Primary or secondary nitroso compounds can exhibit isomerisation as shown below:

 

 

                                                               Isomerisation 

 

Hence, the  nitoso compounds are unstable.

Step 2: Tertiary nitroso compound

The structure of a tertiary nitroso compound is as shown below:

Tertiary nitroso compound

 

The nitrogen is bonded with three alkyl groups and with an oxygen atom.

The tertiary nitroso compound does not consist of any hydrogen atom. So, it will not undergo isomerisation and form any oxime.

 Thus, the tertiary nitroso compound is stable.