CAIE A Level Chemistry 9701 · Nitrogen compounds

Nitrogen compounds: compare question

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A student wants to prepare pentanoic acid, CHX3CHX2CHX2CHX2COOH\ce{CH3CH2CH2CH2COOH}, starting from 1-bromobutane, CHX3CHX2CHX2CHX2Br\ce{CH3CH2CH2CH2Br}. Two possible routes are suggested.

Route 1: Heat 1-bromobutane with KCN\ce{KCN} in ethanol, then hydrolyse the product with dilute HX2SOX4\ce{H2SO4}.

Route 2: Convert 1-bromobutane to butanal, then treat the butanal with HCN\ce{HCN} in the presence of KCN\ce{KCN} and heat, then hydrolyse the product with dilute HX2SOX4\ce{H2SO4}.

Compare these two routes in terms of:

(a) the type of intermediate organic product formed in each route before hydrolysis,

(b) the reagents and conditions needed for each step,

(c) which route is more likely to give a higher yield of pentanoic acid, and why.

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