Question

Write structure of the products of the following reactions:

Hint:

HI cleaves ethers → forms alcohol + alkyl iodide.

Answer 1

(a) Reaction of Anisole (methoxybenzene) with HI: HI protonates the ether oxygen, cleaving the C–O bond. The methyl group is eliminated as methyl iodide (CH$_3$I), yielding phenol (C$_6$H$_5$OH). Products: Phenol and CH$_3$I.

(b) Electrophilic substitution on Phenol: The phenol group strongly activates the benzene ring. Reaction with concentrated nitric acid results in the attachment of multiple nitro groups at the ortho and para positions, forming 2,4,6-trinitrophenol (picric acid). This is a nitration of an activated aromatic compound.

(c) Grignard reaction with Formaldehyde: Cyclohexylmagnesium bromide (Grignard reagent) attacks the carbonyl carbon of formaldehyde, forming an alkoxide intermediate. Acid hydrolysis protonates the alkoxide, producing a primary alcohol. Product: Cyclohexylmethanol (Cyclohexane–CH$_2$–OH).