(a) (i) Phenol to anisole(ii) Ethanol to propan-2-olEthanol (a primary alcohol) when oxidized partially with the partial oxidizing agent such as PCC (Pyridinium chlorochromate) will be converted into acetaldehyde.
If we treat acetaldehyde with Grignard reagent (CH3−Mg−X) followed by acid hydrolysis, we will get propan2-ol which is the desired product. (c) The −OH group attached to the benzene ring in phenol is the highly activating group. The lone pair on oxygen is delocalised into the benzene ring and makes the phenol more electron rich than simple benzene. Thus, phenol undergoes electrophilic substitution more easily than benzene.
OR
(a) (i) o -Nitrophenol forms intramolecular H bond whereas molecules of p-Nitrophenol get associated through intermolecular H bond. During boiling, the strong intermolecular hydrogen bonding increases the boiling point but intramolecular hydrogen bonding cannot do so.
(ii) As the given alkyl halide is tertiary in nature, therefore on reaction with sodium methoxide, elimination reaction takes place in place of substitution and hence, alkene is formed as a major product. Therefore, in the given reaction, 2-methyl propene is formed as a major product.
(b) (i) The Reimer-Tiemann reaction is a chemical reaction used for the o-formylation of phenol. (c) Phenol being more acidic than ethanol will turn the blue litmus paper red but ethanol doesn't. Haloform test is also used to distinguish ethanol and phenol. Ethanol when treated with NaOH and iodine, iodoform is obtained which is yellow needle shaped. But phenol does not show positive haloform test.