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CBSE Class 12 Chemistry 2017 Outside Delhi Set 1 Solved Paper

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Question : 6 of 26
Marks: +1, -0
(a) Arrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenol.
(b) Write the mechanism (using curved arrow notation) of the following reaction:
CH2=CH2CHH→3O+3−C↖+H2+H2O{CH}_2= {CH}_2 \overset{ {H}{ \rightarrow}_3 {O}^{+}} {CH}_3- { {C}}↖{+} {H}_2+ {H}_2 {O}
OR
Write the structures of the products when Butan-2ol reacts with the following :
(a) CrO3{CrO}_3
(b) SOCI2{SOCI}_2
Solution:  
(a) Increasing order of acidic strength:
p-nitrophenol in most acidic due to presence of −NO2- {NO}_2 group i.e., electron with drawing group (-I group) which stabilises phenoxide ion so increases acidity while p-serve is least acidic due to presence of −CH3- {CH}_ 3 group i.e., electron releasing group (+ I group) which destablises phenoxide ion so decreases acidity.
(b) Mechanism:
(i) Electrophilic attack of H3O+{H}_3 {O}^{+}
H2O+H+  "(Fromacid)"  →H3O+{H}_2 {O}+ {H}^{+} \;\text "(From acid) "\; \rightarrow{H}_3 {O}^{+}
(ii) Nucleophilic attack of water on carbocation.
(iii) Deprotonation:
OR
(a) When Butan-2-ol reacts with CrO3{CrO}_3, it forms butan-2-one.
CH3−CH∣OH−CH2−CH3→CrO3{CH}_3- \underset{\mathrm{OH}}{\underset{\vert}{\mathrm{CH}}}- {CH}_2- {CH}_3 \overset{\mathrm{CrO}_3}{\rightarrow} CH3−C∥O−CH2−CH3↙Butan−2−one+H2O{ {CH}_3 - \underset{\mathrm{O}}{\underset{∥}{\mathrm{C}}}- {CH}_2- {CH}_3}↙{Butan-2-one}+ {H}_2 {O}
(b) Butan-2-ol reacts with /SOCl2{/SOCl}_2 to form 2-chlorobutane.
H−C∣H↙∣H−C∣H↙∣OH−C∣H↙∣H−C∣H↙∣H−H+SOCl2→{H}- \overset{\mathrm{H}}{\overset{\vert}{\mathrm{C}}}\swarrow\underset{H}{|}- \overset{\mathrm{H}}{\overset{\vert}{\mathrm{C}}}\swarrow\underset{OH}{|}- \overset{\mathrm{H}}{\overset{\vert}{\mathrm{C}}}\swarrow\underset{H}{|}- \overset{\mathrm{H}}{\overset{\vert}{\mathrm{C}}}\swarrow\underset{H}{|}- {H}+ {SOCl}_2 \rightarrow H−C∣H∣H−C∣H∣Cl−C∣H∣H−C∣H∣H−H2−Chlorobutane+SO2+HCl{{H}- \overset{\mathrm{H}}{\overset{\vert}{\mathrm{C}}}\underset{H}{|}- \overset{\mathrm{H}}{\overset{\vert}{\mathrm{C}}}\underset{Cl}{|}- \overset{\mathrm{H}}{\overset{\vert}{\mathrm{C}}}\underset{H}{|}- \overset{\mathrm{H}}{\overset{\vert}{\mathrm{C}}}\underset{H}{|}- {H}}_{2-\text{Chlorobutane}}+ {SO}_2+ {HCl}
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