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Intramolecular Aldol Condensation

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Question

.Suggest a mechanism for the reaction

)(-)-2-bromaooctane when treated with aqueous NaOH produces (+)-octan-2-ol

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Solution

SN2 mechanism: As there is an inversion in configuration from (-) Bromo-octane to (+) octanol it is clear that the nucleophile has attacked from the opposite side to leaving group.

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Q. When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place:
Give a mechanism for this reaction.
(Hint : The secondary carbocation formed in step II rearranges to a more stable tertiary carbocation by a hydride ion shift from 3rd carbon atom.)

Q. When pent-4-en-1-ol is treated with aqueous bromine in KOH, a cyclic bromo ether is formed rather than the expected bromohydrin. Propose a suitable mechanism for the above.

Q. When pent-4-en-1-ol is treated with aqueous

B r_{2} / O H

, the compound formed is:

1 -

pentene is treated with an acid,

t r a n s - 2 -

pentene is produced. Propose mechanism of this isomerization reaction and justify.

When 3-methylbutan-2-ol is treated with HBr; the following reaction takes place.

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Intramolecular Aldol Condensation

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