Depto. Química Orgánica

THE RESULT OF AN EXPERIMENT

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15/07/2017
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Optically pure (R)-2-bromooctane reacted with sodium hydroxide (a strong nucleophile) in the solvent DMF (dimethylformamide).
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The thorough analysis of the reaction mixture tells us that the result is the major production (80%) of an optically active alcohol,  
together with a series of optically inactive alkenes.
It is reasonable to think that the nucleophile (HO-) has attacked the haloalkane by the electron-deficient carbon of 2-bromooctane, that bonded to the bromine.
Consequently, the alcohol should be 2-octanol.
Let's check a chemical catalog, where we can find the following data:
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The comparison between the measured and tabled optical rotations tells us that the alcohol is mainly (not exclusively) the S enantiomer.
The olefins have been separated and analyzed.
The global result is summarized in the following scheme:
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These results take us to the conclusions that follows:
This logical deductions should allow the proposal of a reasonable reaction mechanism, i.e. a reasonable stepwise sequence describing the precise moment when the bonds are broken and formed.