9701_s16_qp_21
A paper of Chemistry, 9701
Questions:
5
Year:
2016
Paper:
2
Variant:
1

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A reaction sequence is shown. H3C CH2 Br bromoethane H3C CH2 OH ethanol H2C CH2 ethene reaction reaction reaction 1 H3C CH2 CN propanenitrile propanoic acid H3C CH2 C O OH W reaction 3 LiAl H4 reaction 2 Complete the diagram to show the mechanism of reaction 1. Include all necessary charges, partial charges, lone pairs and curly arrows. H3C C H H Br H3C C H H CN + –CN Give the name of the type of reaction involved in reaction 3. The infra-red spectrum of the propanoic acid produced by reaction 2 is shown. transmittance wavenumber / cm–1 Describe and explain the main difference between the infra-red spectrum of W and that of propanoic acid. Reactions 4 and 5 use the same reagent. Give the reagent and conditions needed for reaction 4. reagent conditions Give the conditions needed for reaction 5. Under appropriate conditions, ethanol and propanoic acid undergo a condensation reaction. State the condition necessary for the reaction. Draw the skeletal formula of the organic product of this reaction. Name the organic product of this reaction. Question 5 continues over the page. V reacts with acidified manganate(ions in two different ways depending on the conditions, as shown in the reaction sequence below. propanoic acid H3C CH2 C V T O OH hot, concentrated MnO4 – / H+ cold, dilute MnO4 – / H+ V decolourises bromine water. When the acidified manganate(is hot and concentrated, propanoic acid is the only organic product. When the acidified manganate(is cold and dilute, the organic product is T which has two chiral centres. Give the structural formulae of V and T. V T Identify the types of stereoisomerism shown by V and T. V T