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InterviewSolution
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An unknown alkene of molecular formula `C_(8)H_(16)` on oxidation with hot alkakline `KMnO_(4)` yields propanoic acid and pentanoic acid. Find the structure of the alkene. Strategy: `C_(8)H_(16)underset((2)H_(3)O^(+))overset((1)KMnO_(4)`,H_(2)O,OH^(-)"heat")rarrCH_(3)CH_(2)-underset("acid")underset("Pentanoic")overset(O)overset(||)C-OH+HO-underset("acid")underset("Pentanoic")overset(O)overset(||)C-CH_(2)CH_(2)CH_(2)CH_(3)` Remove the `OH` groups and join the carboxylic acid carbons by a double bond to get the alkene. |
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Answer» The known alkene is either cis-or-trans-oct-`3-"ene"`. Oxidative cleavage takes place as follows: `underset("Unknown alkane either cis-or trans -oct -3 -ene")(CH_(3)CH_(2)-CH!=CH-CH_(2)CH_(2)CH_(2)CH_(3))`underset((2)H_(3)O^(+))overset((1)KMnO_(4),H_(2)O`,`OH^(-)" heat")to` `CH_(3)CH_(2)-overset(O)overset(||)C-OH+CH_(3)CH_(2)CH_(2)CH_(2)-overset(O)overset(||)C-OH` |
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