CBSE Class 12 Chemistry 2015 Solved Paper

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:

2 {\CH}_3 {\CH}_2 {\OH} {\ { ────▸}}↖{ {\H}^{+}} {\CH}_3 {\CH}_2- {\O}

- {\CH}_2 {\CH}_3

(b) Write the equation involved in the acetylation of Salicylic acid.

Solution:

(i)

{\C}_6 {\H}_5 {\OH}+ {\NaOH} { ───▸} {\C}_6 {\H}_5 {\ONa}

\ {  ────▸}↖{ {\CH}_3 {\X}} {\C}_6 {\H}_5 {\OCH}_3

{\C}_6 {\H}_5 {\OH}+ {\Na } { ───▸} {\C}_6 {\H}_5 {\ONa}

\ {  ────▸}↖{ {\CH}_3 {\X}} {\C}_6 {\H}_5 {\OCH}_3

(ii)

{\CH}_3 {\CH}( {\OH}) {\CH}_3 \ {  ──────────▸}↖{ {\CrO}_3 \;\text " or "\; {\Cu} \/ 573 {\K}}

{\CH}_3 {\COCH}_3 \ {  ──  ──  ────▸}↖{(\i){\CH}_3 {\MgX}_2} ↙ {(\ii) \H_2\O}( {\CH}_3) _2 {\C}( {\OH}) {\CH}_3

(iii)

{\C}_6 {\H}_5 {\NH}_2 {\ {  ─ ─────▸}↙{{273 \K}}↖{ {\NaNO}_2+ {\HCl}}}\; {\C}_6 {\H}_5 {\N}^{+}{ }_2 {\Cl}^{-}

\ {  ────▸}↖{ {\H}_2 {\O} \;\text " warm "\;} {\C}_6 {\H}_5 {\OH}

(Acetyl chloride instead of acetic anhydride may be used)

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