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प्रश्न
Explain why p-nitrophenol is more acidic than phenol.
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उत्तर
The electron-withdrawing group (−NO2), withdraws electrons and disperses the negative charge. Therefore, the −NO2 group stabilizes the phenoxide ion. Hence p-nitrophenol is more acidic than phenol.
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\[\begin{array}{cc}
\phantom{.....................................}\ce{CH2OH}\\
\phantom{............................}|\\
\ce{CH3 - CH - CH2 - CH - CH - CH3}\\
|\phantom{....................}|\phantom{............}\\
\ce{CH3}\phantom{..............}\ce{OH}\phantom{.........}\\
\end{array}\]
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\[\begin{array}{cc}
\phantom{........................}\ce{CH3}\\
\phantom{....................}|\\
\ce{CH3 - CH - CH - C - CH3}\\
|\phantom{.........}|\phantom{.........}|\\
\phantom{...}\ce{CH3}\phantom{....}\ce{OH}\phantom{....}\ce{CH3}\\
\end{array}\]
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\[\begin{array}{cc}
\phantom{..}\ce{H}\phantom{...}\ce{CH3}\phantom{.}\ce{H}\phantom{..}\\
\phantom{}|\phantom{....}|\phantom{....}|\phantom{}\\
\ce{H - C - C - C - H}\\
\phantom{}|\phantom{....}|\phantom{....}|\phantom{}\\
\phantom{.}\ce{H}\phantom{...}\ce{OH}\phantom{.}\ce{H}\phantom{.}\\
\end{array}\]
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| Column I | Column II | ||
| (i) | CH3—O—CH3 | (a) |  |
| (ii) | \[\begin{array}{cc} \ce{CH3}\phantom{..................}\\ \backslash\phantom{.............}\\ \ce{CH-O-CH3}\\ /\phantom{..............}\\ \ce{CH3}\phantom{..................} \end{array}\] |
(b) | \[\begin{array}{cc} \ce{CH3}\phantom{....}\\ |\phantom{.......}\\ \ce{CH3-C-I + CH3OH}\\ |\phantom{.......}\\ \ce{CH3}\phantom{....} \end{array}\] |
| (iii) | \[\begin{array}{cc} \ce{CH3}\phantom{.}\\ |\phantom{....}\\ \ce{H3C-C-O-CH3}\\ |\phantom{....}\\ \ce{CH3}\phantom{..} \end{array}\] |
(c) |  |
| (iv) |  |
(d) | CH3—OH + CH3—I |
| (e) | \[\begin{array}{cc} \ce{CH3}\phantom{.....................}\\ \backslash\phantom{.................}\\ \ce{CH-OH + CH3I}\\ /\phantom{.................}\\ \ce{CH3}\phantom{.....................} \end{array}\] |
||
| (f) | \[\begin{array}{cc} \ce{CH3}\phantom{.....................}\\ \backslash\phantom{.................}\\ \ce{CH-I + CH3OH}\\ /\phantom{.................}\\ \ce{CH3}\phantom{.....................} \end{array}\] |
||
| (g) | \[\begin{array}{cc} \ce{CH3}\phantom{....}\\ |\phantom{.......}\\ \ce{CH3-C-OH + CH3I}\\ |\phantom{.......}\\ \ce{CH3}\phantom{....} \end{array}\] |
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