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CBSE Class 12 Chemistry 2015 Solved Paper

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Question : 13 of 26
Marks: +1, -0
How do you convert the following:
(i) Phenol to anisole
(ii) Propan-2-ol to 2-methylpropan-2-ol
(iii) Aniline to phenol
OR
(a) Write the mechanism of the following reaction:
2CH3CH2OHCH3CH2−OH→+2 \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH} \overset{\mathrm{H}{\rightarrow}^{+}}{\mathrm{CH}_3 \mathrm{CH}_2-\mathrm{O}} −CH2CH3- \mathrm{CH}_2 \mathrm{CH}_3
(b) Write the equation involved in the acetylation of Salicylic acid.
Solution:  
(i) C6H5OH+NaOH→C6H5ONa\mathrm{C}_6 \mathrm{H}_5 \mathrm{OH} + \mathrm{NaOH} \rightarrow \mathrm{C}_6 \mathrm{H}_5 \mathrm{ONa} →CH3XC6H5OCH3\xrightarrow{\mathrm{CH}_3 \mathrm{X}} \mathrm{C}_6 \mathrm{H}_5 \mathrm{OCH}_3
Or
C6H5OH+Na→C6H5ONa\mathrm{C}_6 \mathrm{H}_5 \mathrm{OH} + \mathrm{Na} \rightarrow \mathrm{C}_6 \mathrm{H}_5 \mathrm{ONa} →CH3XC6H5OCH3\xrightarrow{\mathrm{CH}_3 \mathrm{X}} \mathrm{C}_6 \mathrm{H}_5 \mathrm{OCH}_3
(ii) CH3CH(OH)CH3→CrO3  or  Cu/573 K\mathrm{CH}_3 \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_3 \xrightarrow{\mathrm{CrO}_3 \;\text{or}\; \mathrm{Cu} / 573 \,\mathrm{K}} CH3COCH3→(ii) H2O(i) CH3MgX(CH3)2C(OH)CH3\mathrm{CH}_3 \mathrm{COCH}_3 \xrightarrow[\text{(ii) } \mathrm{H}_2\mathrm{O}]{\text{(i) } \mathrm{CH}_3\mathrm{MgX}} (\mathrm{CH}_3)_2 \mathrm{C}(\mathrm{OH}) \mathrm{CH}_3
(iii) C6H5NH2→273 KNaNO2+HClC6H5N2+Cl−\mathrm{C}_6 \mathrm{H}_5 \mathrm{NH}_2 \xrightarrow[273\,\mathrm{K}]{\mathrm{NaNO}_2+\mathrm{HCl}} \mathrm{C}_6 \mathrm{H}_5 \mathrm{N}_2^{+} \mathrm{Cl}^{-} →H2O  warm  C6H5OH\xrightarrow{\mathrm{H}_2\mathrm{O} \;\text{warm}\;} \mathrm{C}_6 \mathrm{H}_5 \mathrm{OH}
OR
(Acetyl chloride instead of acetic anhydride may be used)
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