Question

Write the structures of the major products expected from the following reactions:

$A$: Mononitration of 3-methylphenol

$B$: Dinitration of 3-methylphenol

$C$: Mononitration of phenyl methanoate

Answer 1

$A$:

Mononitration of $3-$methylphenol

Mononitration means addition of one nitro group to the compound. As we know that both methyl group $(-C{H}_3)$ and hydroxyl group $(-OH)$ are ortho and para directing and increases electron density at ortho and para positions.

So, electrophile $(\text{nitronium ion},N{O}_2^{+})$ attacks the ortho and para position with respect to hydroxyl group $(-OH)$ and methyl group $(-C{H}_3)$. Moreover, hydroxyl group $(-OH)$ is more electron donating as compared to methyl group $(-C{H}_3)$.

So, the nitro group will be attached at ortho or para position with respect to $(-OH)$ group and replaces $H-atom$ from that position and this reaction is known as electrophilic aromatic substitution.
Major product
So, the major product will be: 3-Methyl-4nitrophenol

$B$:

Dinitration

Dinitration means addition of two nitro group into a compound.

Dinitration of 3-methylphenol

As we know that both methyl group $(-C{H}_3)$ and hydroxyl group $(-OH)$ are ortho and para directing and increases electron density at ortho and para position.
So, the nitro group will be attached at ortho or para position w.r.t. $(-OH)$ group.
Below is the reaction takes place here –
Major product
So, the major product will be: $5-\text{methyl}-2,4-\text{dinitrophenol}$

$C$:

Mononitration
Mononitration means addition of one nitro group to the compound. As we know that $(-OCOC{H}_3)$ is ortho and para directing, and it increases electron density at ortho and para position. So, the nitro group will be attached at ortho and para position with respect to $(-OCOC{H}_3)$ group.

Major product
So, the major product will be: $4-Nitrophenylethanoate$