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Question
How can phenol be converted to aspirin?
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Solution

2-hydroxybenzoic acid on treatment with acetic anhydride will give asprin.
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\[\begin{array}{cc}
\phantom{..}\ce{H}\phantom{...}\ce{CH3}\phantom{.}\ce{H}\phantom{..}\\
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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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\phantom{..............}\ce{CH3}\\
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\ce{CH3 - CH - CH - C - CH3}\\
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\end{array}\]
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\[\begin{array}{cc}
\phantom{................}\ce{CH3}\\
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\ce{CH3 - CH - CH - C - CH3}\\
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