On which structure of C_8H_{10} can we get mono-nitro product with nitration?

Question:

On which structure of {eq}\rm C_8H_{10} {/eq} can we get mono-nitro product with nitration?

Substitution Reactions:

Substitution can occur in aromatic and aliphatic compounds. Mono-substitution, di- substitution or more than two substitutions can occur depending on the stability of the product and type of reagents used.

Answer and Explanation:


The given molecular formula is {eq}{{\rm{C}}_{\rm{8}}}{{\rm{H}}_{{\rm{10}}}} {/eq}. Nitration usually occurs in an aromatic compound. Here, nitration will occur in benzene derivatives.

The derivate with formula {eq}{{\rm{C}}_{\rm{8}}}{{\rm{H}}_{{\rm{10}}}} {/eq} that gives mono-nitro product is p-xylene. o-xylene and m-xylene can produce more than one mono-nitro product and also di-nitro products.

The reason is that, methyl group is ortho para directing group and thus only ortho substitution to one of the methyl group takes place. Substitution in other positions is not stable.

The reaction for the above mentioned compound is given below.

Therefore, the structure with formula {eq}{{\rm{C}}_{\rm{8}}}{{\rm{H}}_{{\rm{10}}}} {/eq} that gives mono-nitro product is p-xylene.


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