Lawrie Ryan and Roger Norris Solutions for Chapter: Benzene and its Compounds, Exercise 9: Question

Place these molecules in order of ease of nitration, with the most reactive first:

${\mathrm{C}}_6{\mathrm{H}}_6 {\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{CH}}_3 {\mathrm{C}}_6{\mathrm{H}}_5\mathrm{COOH} {\mathrm{C}}_6{\mathrm{H}}_5\mathrm{OH}$.

Write a balanced equation to show the reaction when excess chlorine is bubbled through aqueous phenol at room temperature.

How would the reaction conditions differ from those in excess chlorine is bubbled through aqueous phenol at room temperature if you wanted to make chlorobenzene from benzene and chlorine?

Predict the reaction of excess $1$-naphthol with potassium hydroxide solution, and draw one of the organic product formed.

Predict the reaction of excess $1$-naphthol with sodium metal, and draw one of the organic product formed.

Predict the reaction of excess $1$-naphthol with bromine water, and draw one of the organic product formed.

Predict the reaction of excess $1$-naphthol with dilute nitric acid, and draw one of the organic products formed.