Draw the structures of major monohaloge products in each of the following reactions.

Explanation

Since benzylic radicals are more stable, therefore, benzylic hydrogen is abstracted.

Only alcoholic but not phenolic OH groups are replaced by Cl on heating with HCl.

Iodide ion is a stronger nucleophile and hence it displaces bromide ion. further, since NaBr is insoluble while NaI is soluble in dry acetone, therefore, the equilibrium shifts in the forward direction.
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In presence of heat and light, allylic bromination occurs to form 3-bromocyclohex-1-ene.