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Question 1
2-Bromopropane reacts with aqueous potassium hydroxide to form potassium bromide and an alcohol. |
a) | Name the mechanism for this reaction.
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b) | Outline the mechanism for this reaction.
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c) | Name the alcohol formed in the reaction.
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d) | Identify the characteristic of the halogenoalkane that enables it to undergo this reaction.
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Question 2
This question is about the reaction of halogenoalkanes to form alkenes. |
a) | Write an equation for the reaction between 2-bromopropane and potassium hydroxide to form propene and two other products.
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b) | Name the mechanism for this reaction.
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c) | Outline the mechanism for this reaction.
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d) | Give one condition needed to favour this mechanism instead of a nucleophilic substitution to form an alcohol.
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Question 3
1-Chloroethane can react with methoxide ions, CH3O−, by nucleophilic substitution. |
a) | Suggest how CH3O− ions can act as a nucleophile.
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b) | Outline the mechanism for this reaction.
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c) | 1-Iodoethane also reacts with methoxide ions. Explain how the use of 1-iodoethane instead of 1-chloroethane would affect the rate of reaction.
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d) | The ethanoate ion, CH3COO−, also acts as a nucleophile when it reacts with 1-chloroethane. Name the organic product formed in this reaction and draw its skeletal formula.
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Question 4
This question is about the rate of hydrolysis of halogenoalkanes. |
a) | State and explain how the halogen in a halogenoalkane affects the rate of hydrolysis.
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b) | Name the halogenoalkane shown in the diagram below.
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c) | The reaction of the halogenoalkane in part b) with aqueous potassium hydroxide forms an alcohol. Name and outline the mechanism for this reaction.
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d) | Explain why the reaction of 3-iodo-2,4-dimethylpentane with aqueous potassium hydroxide would be quicker than with the bromoalkane.
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Question 5
The diagram below shows the structure of bromoalkane X. |
a) | Name bromoalkane X.
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b) | Suggest one reason why 1-bromohexane has a higher boiling point than bromoalkane X.
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c) | Draw the displayed formula of 1,2-dichloro-2-methylpropane.
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d) | 1-Chloro-2-methylpropane reacts with ammonia to form an amine. Name and outline the mechanism for this reaction.
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Question 6
The diagram below shows some compounds made from a halogenoalkane. |
a) | Draw the displayed formula of alcohol Y.
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b) | Name the mechanism in reaction 2 and give an essential condition required to ensure CH3CH2CH2NH2 is the major product.
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c) | When reaction 2 is carried out under different conditions a compound with the molecular formula C9H21N is formed. Draw the skeletal formula of the compound and identify its functional group.
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d) | Identify the reagents and conditions required for reaction 3.
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Question 7
A student hydrolysed 1-bromobutane and 1-chlorobutane using aqueous sodium hydroxide. |
a) | State and explain the difference in the rates of hydrolysis of 1-bromobutane and 1-chlorobutane.
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b) | The molecular formula of an iodoalkane is C4H9I. Draw the four possible structural isomers of this compound.
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c) | Outline the mechanism for the reaction between 1-iodobutane and aqueous sodium hydroxide.
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d) | Name the organic product formed in the reaction in part c).
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Question 8
The halogenoalkane 1-bromopropane can be converted into propan-1-ol in a one-step reaction. |
a) | State the reagent and condition needed for this reaction.
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b) | Outline a mechanism for this reaction.
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c) | 1-Bromopropane is reacted with KOH dissolved in ethanol. Name and outline a mechanism for this reaction.
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d) | Name the organic product formed in the reaction in part c).
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Question 9
This question is about the halogenoalkane 1-chloropropane. |
a) | Write a balanced equation for the reaction between 1-chloropropane and aqueous hydroxide ions.
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b) | The hydroxide ions act as a nucleophile in this reaction. State two features of the hydroxide ion that enable it to act as a nucleophile.
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c) | Explain how the rate of reaction would change if 1-iodopropane was used as a reagent instead.
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Question 10
This question is about the reactions of bromoalkanes. |
a) | Complete the diagram below to show the SN2 mechanism for the reaction between 1-bromopropane and aqueous NaOH.
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b) | Explain why the reaction between 2-bromo-2-methylpropane and aqueous NaOH will react via a different mechanism to that in part a).
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c) | Bromoethane reacts with potassium cyanide, KCN, to form compound X and KBr. Outline the mechanism for this reaction.
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d) | Name compound X.
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| 7 | 8 | 9 | 10 |