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CAIE A Level Chemistry 9701 · Organic synthesis

Organic synthesis: compare question

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A student plans two separate preparations from the keto-ester ethyl 3-oxobutanoate, which contains both an ester group and a ketone group.

Route 1: the keto-ester is heated under reflux with an excess of aqueous sodium hydroxide, then acidified.

Route 2: the keto-ester is first treated with an excess of aqueous sodium borohydride, then the product is hydrolysed by heating under reflux with aqueous sodium hydroxide, then acidified.

Compare the two routes in terms of the functional groups present in the final organic product, and suggest the type of reaction and possible by-products for each step of Route 2.

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5 marks, so the mark scheme is looking for about 5 separate creditworthy points. Making the same point twice in different words earns it once.

Compare means: Give similarities or differences between two things, and say which side each point belongs to. Write each point as a pair, for example: A is X, whereas B is Y. Two separate descriptions rarely earn the marks.

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