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Dolbier HW Solutions 206

Dolbier HW Solutions 206 - b To decide on the best sequence...

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Unformatted text preview: ( b ) To decide on the best sequence of reactions, we must begin by writing structural formulas to determine what kinds of transformations are required. We already know from part ( a ) how to convert trans-2-methylcyclopentanol to cis-2-methyl- cyclopentyl acetate. So all that is really necessary is to design a synthesis of trans-2-methyl- cyclopentanol. Therefore, Hydroboration – oxidation converts 1-methylcyclopentene to the desired alcohol by anti- Markovnikov syn hydration of the double bond. The resulting alcohol is then converted to its p-toluenesulfonate ester and treated with acetate ion as in part ( a ) to give cis-2-methyl- cyclopentyl acetate. 8.35 ( a ) The reaction of an alcohol with a sulfonyl chloride gives a sulfonate ester. The oxygen of the alcohol remains in place and is the atom to which the sulfonyl group becomes attached. ( b ) Sulfonate is similar to iodide in its leaving-group behavior. The product in part ( a ) is attacked by NaSCH 2 CH 3 in an S N 2 reaction. Inversion of con2 reaction....
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