Alcohols and phenols

Question 1

Why can’t phenol undergo nucleophilic substitution?

Answer 1

The p orbital of the O atom overlaps with the pi electron cloud of the ring, allowing the lone pair of electrons on the oxygen to delocalise into the ring. This results in a partial double bond character and thus a strengthened C-O bond that is difficult to break.

Question 2

State the ratio of the iodoform test for alcohols with the structural fragment.

Answer 2

4:6:5:5
in the order of reactant (iodine), medium (OH-), product (iodide ions) and water (H2O)