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Colour by Design

Choosing between routes on yield and atom economy

  • 1 thing to know
  • Components 01, 02 and 03

Overview

Recall questions on multiplying step yields, why fewer steps are preferred, and comparing two routes on atom economy.

What you need to know

Answer each one before you reveal it.

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Numbers

Adding HCN to ethanal has an atom economy of 100%, while CH₃CH₂Br + KCN → CH₃CH₂CN + KBr has 31.6%. Why might a chemist still choose the cyanide substitution route?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    Why is there no need to memorise the reactions printed on the Data Sheet?

    Model answer

    They are available during the examination, so the skill required is recognising when a route needs one and applying it with the right conditions.

  2. 2

    Suggest a route from propan-1-ol to butanoic acid.

    Model answer

    Replace the –OH group with bromine by heating with sodium bromide and concentrated sulfuric acid to give 1-bromopropane, reflux this with potassium cyanide in ethanol to give butanenitrile, then reflux the nitrile with aqueous acid to give butanoic acid.

  3. 3

    Suggest how 2-hydroxypropanoic acid could be made from ethanal.

    Model answer

    Add hydrogen cyanide to the ethanal to give 2-hydroxypropanenitrile, then heat this under reflux with aqueous acid to hydrolyse the nitrile group to –COOH.

  4. 4

    What must be stated alongside the reagent at every stage of a proposed synthetic route?

    Model answer

    The conditions: the solvent, the temperature, any catalyst, and whether the mixture is refluxed or distilled.

  5. 5

    Why is a route with fewer steps generally preferred?

    Model answer

    Every step loses some product, so the overall yield falls sharply as steps are added, and each step also costs time, energy and reagents.

  6. 6

    A three-step synthesis has step yields of 80%, 70% and 75%. Calculate the overall percentage yield.

    Model answer

    The overall yield is 0.80 × 0.70 × 0.75 = 0.42, that is 42%.

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