A chemist was attempting to make the compound below. They dissolved the required

Question

A chemist was attempting to make the compound below. They dissolved the required carbonyl reactant in methanol, added the solution to a round-bottom flask and then added acetic acid. A Dean-Stark trap with a reflux condenser was fitted onto the round-bottom flask and the solution was brought to boiling. The chemist, however, did not observe an aqueous layer in the Dean-Stark trap. Additionally, analysis of the mixture indicated that no reaction had taken place and the carbonyl reactant was recovered. First, list the reasons this reaction would not be successful (at least 5). Second, explain why each error would impede the reaction. Third, suggest specific modifications that the chemist should make to correct each error.

Explanation / Answer

The reaction is used for protecting the carbonyl group by treating the corresponding the ketone with ethane diol

reason for failure

reaction will not occur in ester carbonyl group

the reaction medium is the problem because the methanol will also react to form acetal

secondly in methanol water will be there it will also affect the reaction

reaction medium should be non-polar

reaction medium should be in dry medium without moisture and water

modification in reaction

replace the ester to ketone

proceed the reaction in non polar solvent and in dry condition

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