Syllabus Edition
First teaching 2014
Last exams 2024
Define the term nucleophile.
Explain why the hydroxide ion, OH- , is a stronger nucleophile than water.
State the two ways a nucleophilic substitution reaction can occur.
State the the name of the mechanism occurring in the image below which will form ethanol in one step.
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The start of the electrophilic addition mechanism for the addition of hydrogen bromide to ethene is shown below:
Complete the mechanism by:
Draw the product of the reaction in part a).
The electrophilic addition of hydrogen bromide to but-1-ene results in two isomeric products - one is a major product and one is a minor product. The first steps of the electrophilic addition mechanism are shown below:
Explain why the secondary carbocation is more stable than the primary carbocation.
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Name the type of mechanism that benzene will undergo in order to form nitrobenzene.
State the reagents required to form nitrobenzene from benzene.
Phenylamine, C6H5NH2 , can be formed from nitrobenzene. State the reagents required.
Outline the mechanism for the formation of nitrobenzene from benzene.
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State what is meant by the term protic, polar solvent.
State what is meant by the term aprotic , polar solvent
State which type of solvent is best suited to the following nucleophilic substitution reactions.
Identify the type of reaction that converts aldehydes and ketones to their corresponding parent alcohol.
Name a reducing agents that can convert aldehydes and ketones into their corresponding alcohols.
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2-chloro-2-methylpropane is reacted with aqueous sodium hydroxide in ethanol and heated under reflux.
Outline the mechanism for the reaction given in part a).
State the type of bond breaking that occurs in this mechanism.
A student stated that changing the halogenoalkane for the reaction in part a) to 2-iodo-2-methylpropane, the reaction would be quicker. Is the student correct? Explain your answer.
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Halogen molecules can react with alkenes to produce halogenoalkanes which contain two halogen atoms. Explain why halogen molecules can react with alkenes.
Outline the mechanism for the reaction between 1-methylcyclohex-1-ene and hydrogen bromide, HBr, to form the major product.
Explain why a major product and minor product are produced in the reaction outlined in part b).
The major product from the reaction of part b) forms an alcohol when reacted with water. Predict the type of mechanism for this reaction and the structure of the alcohol.
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C5H11Cl is a chiral molecule.
Draw the three-dimensional shape of each enantiomer of this isomer showing their spatial relationship to each other
One of these enantiomers undergoes alkaline hydrolysis and approximately 75 % of the product formed shows an inversion of configuration.
Outline the mechanism that causes approximately 100% of the inversion of configuration.
Explain why the inversion of configuration is 75%.
Explain what would happen to the rate of the mechanism in part b) if the concentration of alkali is doubled.
Comment on the rate if ammonia was reacted with C5H11Cl compared to alkaline hydrolysis.
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The theoretical molecule cyclohexa-1,3,5-triene reacts differently with bromine than benzene.
Benzene will react with bromine in the presence of aluminium bromide. Outline the mechanism for this reaction.
State the name of the mechanism that occurs during the reaction between cyclohexa-1,3,5-triene and bromine.
The nitration of benzene is the first important step in the manufacture of dyes and explosives.
Phenylamine can be formed from nitrobenzene in two steps. The first step involves heating nitrobenzene in a water bath under reflux with a mixture of zinc and hydrochloric acid.
Explain why benzene can only undergo substitution reactions.
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Aqueous sodium tetrahydridoborate, NaBH4, is a common reducing agent.
State the IUPAC name of the two isomers with the formula C3H6O that can be reduced by aqueous NaBH4.
State the IUPAC name of two non-cyclic isomers with the formula C3H6O that cannot be reduced by aqueous NaBH4.
When NaBH4 is used as a reducing agent followed by the addition of acid, the reduction products of ketones can exhibit optical isomerism, while the reduction products of aldehydes cannot.
Deduce the structure when the following compound is reduced using NaBH4.
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The results of a series of experiments performed to determine the order of reaction between an isomer of bromobutane, C4H9Br, and aqueous sodium hydroxide are shown.
|
Experiment |
[C4H9Br] / mol dm-3 |
[OH-] / mol dm-3 |
Initial rate / mol dm-3 s-1 |
|
1 |
0.10 |
0.20 |
2.90 x 10-4 |
|
2 |
0.15 |
0.20 |
4.35 x 10-4 |
|
3 |
0.30 |
0.40 |
8.70 x 10-4 |
Determine, explaining your method, the rate expression for the reaction of the bromobutane isomer with aqueous sodium hydroxide.
Use your answer to (a) to deduce the type of mechanism for the reaction of the bromobutane isomer with aqueous sodium hydroxide, explain your reasoning.
Sketch the mechanism, using curly arrows to represent the movement of electrons.
State, giving your reason, the role of the hydroxide ion in the nucleophilic substitution.
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The starting material for many products are alkenes such as propene.
State the type of reaction that occurs when propene is converted into chloropropane.
Two possible isomeric products can be formed in the conversion of propene to chloropropane.
State the type of isomerism that is exhibited by these chloropropane products.
Explain the mechanism of the reaction that forms the major product when propene is converted to chloropropane using curly arrows to represent the movement of electron pairs.
Outline why the major product is formed.
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Kekulé proposed the following structure of benzene.
Discuss the physical and chemical evidence to suggest that the Kekulé structure of benzene is incorrect.
State the reagents and the name of the mechanism used to convert benzene into nitrobenzene.
Using your answer to (b), formulate the equation for the formation of the nitronium ion.
Using curly arrows to indicate the movement of electron pairs, explain the mechanism for the nitration of benzene.
Nitrobenzene can be converted into aniline in a two-step process. State the reagents for this conversion.
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State a halogenoalkane reactant that can be used to slowly produce butan-1-ol by reacting with aqueous sodium hydroxide.
Butan-1-ol can also be formed by the catalytic reduction of butanal. State the reagents for this reduction to occur
State the reagent required to reduce butanoic acid to butan-1-ol.
Using your answer to (c), write the equation for the reduction reaction of butanoic acid.
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1-bromobutane and 2-bromo-2-methylpropane are isomers. State the type of structural isomerism that they exhibit, explaining your reasoning.
Using curly arrows to indicate the movement of electron pairs, explain the mechanism for the reaction of 1-bromobutane with aqueous sodium hydroxide.
Consider the reactions of 1-bromobutane and 2-bromo-2-methylpropane with aqueous sodium hydroxide.
Compare and contrast the mechanisms for these reactions.
Explain why an inversion of configuration occurs during the reaction described in (c).
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