Question

Write structure of the products of the following reactions:

Hint:

HI cleaves ethers → forms alcohol + alkyl iodide.

Answer 1

(a) Anisole (methoxybenzene) reacts with HI.
HI protonates the ether oxygen and breaks the C–O bond. 
The methyl group leaves as methyl iodide (CH$_3$I) and phenol (C$_6$H$_5$OH) is formed. 
So, products are: Phenol + CH$_3$I.

(b) Phenol activates the benzene ring strongly towards electrophilic substitution. 
With concentrated nitric acid, multiple nitro groups attach to ortho and para positions. 
So, 2,4,6-trinitrophenol (picric acid) is formed. 
This reaction is an example of nitration of an activated aromatic compound.

(c)The Grignard reagent (Cyclohexyl–MgBr) attacks the carbonyl carbon of formaldehyde. 
This forms an alkoxide intermediate. 
On acid hydrolysis, the alkoxide is protonated to give a primary alcohol. 
So, the product is cyclohexylmethanol (Cyclohexane–CH$_2$–OH).