(i) Phenoxide ion is generated by treating phenol with sodium hydroxide which is even more reactive than phenol towards electrophilic aromatic substitution. Hence, it undergoes electrophilic substitution with carbon dioxide which is a weak electrophile. Ortho hydroxybenzoic acid is formed as the main reaction product.
(ii) Anisole undergoes Friedel-Crafts acylation, i.e., acyl groups are introduced at ortho and para positions by reaction with acyl halide in the presence of anhydrous aluminium chloride (a Lewis acid) as catalyst.
(b) (i) Ethanol and phenol
Phenol gives a violet coloration with FeCl3 solution but ethanol does not.
(ii) Propan-2-ol and 2-methylpropan-2-ol
Propan-2-ol when warmed with NaOI (I2/NaOH) gives yellow precipitate of iodoform while 2-methylpropan-2-ol does not.
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