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Question
Write the IUPAC name of the following compound:
\[\begin{array}{cc}
\ce{CH3 - CH - CH - CH3}\\
|\phantom{.........}|\phantom{...}\\
\ce{OH}\phantom{....}\ce{OH}\\
\end{array}\]
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Solution
Butane-2,3-diol
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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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\[\begin{array}{cc}
\ce{CH3 - CH - O - CH2 - CH2 - CH3}\\
|\phantom{....................}\\
\ce{CH3}\phantom{.................}
\end{array}\] is 2-Ethoxy-2-methylethane.
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Reason: –OH group in phenol is o–, p– directing.
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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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