Questions
Q1.
The reaction of 2-bromobutane with aqueous alkali is a nucleophilic substitution.
C4H9Br + NaOH → C4H9OH + NaBr
Depending on the conditions, the mechanism of this reaction may be SN1 or SN2.
(a) Experiments were carried out to determine the rate equation for a reaction of
2-bromobutane with aqueous sodium hydroxide.
In each experiment, the reactants were mixed and the concentration of
2-bromobutane was measured at various times as the reaction proceeded.
The initial rate of the reaction was determined using these data.
(i) Describe how the initial rate would be determined from the results of one experiment.
(3)
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(ii) Give a reason why the concentration of sodium hydroxide used was very
much greater than the concentration of 2-bromobutane.
(1)
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(b) The results of a set of experiments are shown.
(i) By referring to the data in the table, show that the reaction was first order
with respect to both C4H9Br and NaOH.
(2)
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(ii) Calculate the rate constant for the reaction.
Use the data from experiment 1 and include units with your answer.
(2)
(c) (i) State why the reaction of 2-bromobutane with aqueous sodium hydroxide
being second order indicates an SN2 mechanism.
(1)
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(ii) Draw the first step of the mechanism, showing the transition state in the
SN2 mechanism for the reaction of 2-bromobutane with aqueous sodium hydroxide.
Include curly arrows, and any relevant dipoles and lone pairs of electrons.
(3)
(d) 2-bromobutane and butan-2-ol are chiral molecules.
(i) State the meaning of the term chiral molecule.
(1)
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* (ii) When a single enantiomer (optical isomer) of 2-bromobutane reacts with
aqueous alkali, the stereochemistry of the butan-2-ol formed depends on
whether the mechanism is SN1 or SN2.
Explain how the stereochemistry of the butan-2-ol differs with the
different mechanisms.
(4)
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(Total for question = 17 marks)
Mark Scheme
Q1.
