AS Cambridge (CIE) Chemistry 2 hours 12 questions
Structured Questions
Halogenoalkanes
Producing Halogenoalkanes / Substitution Reactions of Halogenoalkanes /
Elimination Reactions of Halogenoalkanes / SN1 & SN2 / Reactivity of
Halogenoalkanes
Easy (3 questions) /24 Scan here to return to the course
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Medium (5 questions) /76
Hard (4 questions) /47
Total Marks /147
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Easy Questions
1 (a) The structure of a halogenoalkane containing bromine is shown in Fig. 1.1.
Fig. 1.1
i) Name the compound shown in Fig. 1.1.
[1]
ii) State the class of halogenoalkane to which this compound belongs.
[1]
(2 marks)
(b) State the colour of the precipitate formed in the reaction between the halogenoalkane in
Fig. 1.1 in part (a) and acidified silver nitrate, AgNO3.
(1 mark)
(c) The compound drawn in Fig. 1.1 in part (a) is reacted with alcoholic potassium cyanide,
KCN. The reaction is heated under reflux.
Draw the product of this nucleophilic substitution reaction.
(1 mark)
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(d) The halogenoalkane drawn in Fig. 1.2 contains a chlorine atom instead of a bromine
atom. This halogenoalkane is reacted under the same conditions outlined in part (c).
Fig. 1.2
The reaction for a halogenoalkane containing bromine would be faster than if the
compound in Fig. 1.2 was used. Briefly explain why this reaction would be faster.
(2 marks)
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2 (a) Fig. 2.1 shows the reaction profile for the production of propene.
step 1 step 2
Propane ⎯⎯⎯⎯⎯⎯⎯⎯ 1-chloropropane ⎯⎯⎯⎯⎯⎯⎯⎯ Propene
Fig. 2.1
i) State the conditions required for step 1.
[2]
ii) Name the mechanism for step 1.
[1]
(3 marks)
(b) The mechanism for step 1 in part (a) involves three different steps, initiation,
propagation and termination.
Initiation:
Cl2 → 2Cl●
Propagation:
Equation 1
Equation 2
Termination:
Cl● + CH3CH2CH2●
The two propagation steps are missing. Write both of the equations that are required for
this step.
(2 marks)
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(c) i) Name the mechanism for step 2.
[1]
ii) State the reagent and necessary conditions for step 2.
[3]
(4 marks)
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3 (a) Many of the reactions of halogenoalkanes involve a nucleophile attacking the carbon
attached to the halogen atom. The nucleophile replaces the halogen atom in a
nucleophilic substitution reaction.
The mechanism for the reaction is determined by the structure of the halogenoalkane.
Primary and tertiary halogenoalkanes react via different reaction mechanisms.
i) State what is meant by the term tertiary halogenoalkane.
[1]
ii) Tertiary halogenoalkanes react via an SN1 mechanism, whereas primary
halogenoalkanes react via an SN2 mechanism.
Explain what the numbers 1 and 2 refer to in SN1 and SN2.
[1]
(2 marks)
(b) 2-bromo-2-methylpropane reacts with hydroxide ions via an SN1 mechanism.
i) The incomplete reaction mechanism for the reaction is shown in Fig. 3.1
Complete the reaction mechanism shown in Fig. 3.1 clearly showing any partial charges,
full charges and the transfer of electrons.
[3]
Fig. 3.1
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ii) Identify which, step 1 or step 2, is the rate-determining step.
[1]
(4 marks)
(c) An ethanolic solution of excess ammonia (NH3 in ethanol) is heated under pressure with
2-bromo-2-methylpropane.
i) Draw the structure of the resulting organic product.
[1]
ii) State the name of the functional group of the organic product.
[2]
(3 marks)
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Medium Questions
1 (a) The molecular formula C3H6 represents the compounds propene and cyclopropane are
shown in Fig. 1.1.
propene cyclopropane
Fig. 1.1
What is the H–C–H bond angle at the terminal =CH2 group in propene?
(1 mark)
(b) Under suitable conditions, propene and cyclopropane each react with chlorine.
i) With propene, 1,2-dichloropropane, CH3CHClCH2Cl is formed. State fully what type of
reaction this is.
[1]
ii) When cyclopropane reacts with chlorine, three different compounds with the
molecular formula C3H4Cl2 can be formed. Draw displayed structures of each of these
three compounds.
[3]
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(4 marks)
(c) Ethane reacts with chlorine according to the following equation.
C2H6 + Cl2 → C2H5Cl + HCl
i) State the conditions needed for this reaction.
[1]
ii) State the type of reaction occurring here.
[1]
(2 marks)
(d) i) One of the steps during the reaction in (c) is the following process.
Cl● + CH3CH3 → HCl + CH3CH2●
Table 1.1
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Bond Bond enthalpy / kJ mol-1
C–H 410
H–Cl 431
H–I 299
Use the data in Table 1.1 to calculate the enthalpy change, ∆H, of this step.
Show your working.
[1]
∆H = ................................ kJ mol–1
ii) Use the data in Table 1.1 to calculate the enthalpy change, ∆H, of the similar reaction:
I● + CH3CH3 → HI + CH3CH2●
Show your working.
[1]
∆H = ................................ kJ mol–1
iii) Hence suggest why it is not possible to make iodoethane by reacting together iodine
and ethane.
[1]
(3 marks)
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(e) Complete the following equations of some possible steps in the formation of
chloroethane.
Cl2 → ..............
Cl● + CH3CH3 → HCl + CH3CH2●
CH3CH2● + .............. → ........................ + ..............
.............. + .............. → CH3CH2Cl
(3 marks)
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2 (a) This question concerns halogenoalkanes.
1-chloropropane can react to form organic products as shown in the reaction scheme in
Fig. 2.1.
Fig. 2.1
i) State the reagent and conditions used in Reaction 1.
[2]
ii) Identify a suitable reagent for Reaction 2 and include a reason why this is a particularly
useful type of reaction in organic chemistry.
[2]
Reagent ..................................................
Reason ..................................................
iii) State the conditions which are used in Reaction 3.
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[2]
iv) Write the structural formula of the product that will be formed if 1-chloropropane is
refluxed with aqueous sodium hydroxide solution.
[1]
(7 marks)
(b) 2‐chloro‐2‐methylpropane can be reacted with aqueous alkali to form 2-methylpropan-
2-ol.
The equation for this reaction is
(CH3)3CCl + OH− → (CH3)3COH + Cl−
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The graph in Fig 2.2 shows how the concentration of 2‐chloro‐2‐methylpropane changes
with time during an investigation of this reaction.
Fig. 2.2
Calculate the rate of reaction at 50 s. Show your working on the graph. Include units with
your final answer.
Rate of reaction at 50 s = ............................
(3 marks)
(c) What is the classification of the mechanism for the reaction of 2‐chloro‐2‐
methylpropane with aqueous alkali?
(1 mark)
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(d) The letters X, Y and Z refer to three different halogenoalkanes:
X 1‐bromobutane
Y 1‐iodobutane
Z 1-chlorobutane
1 cm3 of each of these halogenoalkanes was added to separate test tubes containing 5
cm3 of ethanol and 5 cm3 of aqueous silver nitrate solution in a water bath at 50 °C.
i) State the visible change in the reaction of an ethanol/silver nitrate solution with
halogenoalkane X.
Include the formula of the compound responsible for this observation.
[2]
ii) The three halogenoalkanes were placed in order of decreasing rate of reaction.
State the order, starting with the halogenoalkane that reacted the fastest
[1]
(3 marks)
(e) 2-bromo-2-methylpropane can be prepared from the addition of hydrogen bromide,
HBr, to 2-methylpropene.
Draw the mechanism for this reaction. Include curly arrows, and any relevant dipoles
and lone pairs.
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(4 marks)
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3 (a) One method of making 1-bromobutane in the laboratory is described below.
Step Place 35 g of powdered potassium bromide, 30 cm3 of water, and 25 cm3 of
1 butan-1-ol, in a 250 cm3 two necked flask fitted with a tap funnel and reflux
condenser.
Step Concentrated sulfuric acid (25 cm3) is then placed in the tap funnel and added
2 drop by drop to the reagents in the flask, keeping the contents well shaken
and cooled occasionally in an ice-water bath.
The overall reaction may be considered to take place in two stages. In the first stage, the
inorganic reagents react together to form HBr. In the second stage, the organic reagent
reacts with the HBr that is formed in the first stage.
Write an equation for each of these stages.
Stage 1 ..............................................................................................................................
Stage 2 ..............................................................................................................................
(2 marks)
(b) 1-bromobutane can be prepared using different reagents and conditions.
State two different ways that 1-bromobutane can be prepared. In each case, include the
reagents and conditions that are necessary
(2 marks)
(c) i) Complete the following reaction scheme shown in Fig. 3.1 which starts with 1-
bromobutane.
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In each empty box, write the structural formula of the organic compound that would be
formed.
Fig. 3.1
ii) State the name of the type of reaction that occurs when X is produced from 1-
bromobutane.
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(5 marks)
(d) Compound W can also be formed from 1-bromobutane by heating it under reflux with
aqueous silver nitrate. This causes the hydrolysis of 1-bromobutane.
Suggest why the rate of the formation of compound W is slower using this method than
heating under reflux with aqueous sodium hydroxide.
(2 marks)
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4 (a) This is a question about the hydrolysis of halogenoalkanes.
Devise an experiment, giving outline details only, that would enable the relative rates of
hydrolysis of halogenoalkanes to be compared.
(5 marks)
(b) Explain the trend in the rates of hydrolysis of 1-chlorobutane, 1-bromobutane and 1-
iodobutane.
(2 marks)
(c) The product of the hydrolysis of 2-bromobutane is butan-2-ol. Both molecules are chiral.
State what is meant by the term chiral, using three-dimensional diagrams of the
enantiomers of butan-2-ol to illustrate your answer.
(3 marks)
(d) Compare and contrast the mechanism of hydrolysis, using aqueous sodium hydroxide,
of the primary halogenoalkane, RCH2X, with that of the tertiary halogenoalkane, R3CX.
Include diagrams of any intermediate or transition state.
Curly arrows are not required.
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(6 marks)
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5 (a) Give the structures of the four structural isomers of C4H9Br and identify each as primary,
secondary or tertiary.
(4 marks)
(b) Name the isomer of C4H9Br that contains a chiral centre and draw the three-dimensional
structures of the two optical isomers.
name ..................................................................
structures
(3 marks)
(c) Aqueous silver nitrate solution was added to separate tubes containing chloroethane,
bromoethane and iodoethane. The tubes were heated in a water bath.
A yellow precipitate appeared first in the tube containing iodoethane, followed by a
cream precipitate in the tube containing bromoethane and finally a white precipitate
appeared in the tube containing chloroethane.
Explain these observations.
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(2 marks)
(d) i) Give the full name of the mechanism for the reaction between aqueous sodium
hydroxide and bromoethane.
[2]
ii) Complete the diagram below to represent this mechanism. Include all necessary curly
arrows, partial charges and lone pairs.
[2]
(4 marks)
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(e) Primary and teriary halgenoalkanes have different reaction mechanisms when they react
with aqueous sodium hydroxide.
i) State the name that is given to the reaction mechanism when aqueous sodium
hydroxide is reacted with the following types of halogenoalkane.
primary halogenoalkane .......................................................................................
tertiary haologenolkane ......................................................................................
[2]
ii) Tertiary halogenoalkanes form a tertiary carbocation as an intermediate during this
reaction. Explain why tertiary carbocations are more stable than primary carbocations.
[3]
(5 marks)
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Hard Questions
1 (a) This question is about halogenoalkanes.
A student investigates the rate of reaction of six halogenoalkanes using the following
method.
1. Mix ethanol with six drops of halogenoalkane.
2. Warm the mixture in a water bath at 50 °C.
3. Add silver nitrate solution.
4. Record the time taken for the precipitate to form.
Table 1.1 shows the student's results.
Table 1.1
Halogenoalkane Time taken for the precipitate to form (s) at 50 °C
CH3CH2CH2CH2CH2Cl 265
CH3CH2CH2CH2CH2Br 152
CH3CH2CH2CH2CH2I 65
CH3CH2CH2CHBrCH3 88
(CH3)2CHCHClCH3 190
CH3CH2C(CH3)2Cl 88
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i) Suggest how the student could improve the method.
[3]
ii) Other than precipitation, state what type of reaction is occurring in this method.
[1]
(4 marks)
(b) Using Table 1.1, describe and explain two factors that influence the rate of this type of
reaction in halogenoalkanes.
(4 marks)
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(c) A fresh sample of aqueous 1-bromopentane reacts with an aqueous solution of sodium
hydroxide.
i) Fully identify the mechanism for this reaction and state the number of steps in the
mechanism.
[1]
ii) One of the products contains bromine. Name this product.
[1]
iii) The reaction conditions are changed resulting in the formation of three products,
including the product identified in part (c)(ii).
Suggest the change that is made to the conditions.
[1]
(3 marks)
(d) 1-chloropentane was prepared in the laboratory by the reaction of an alcohol and thionyl
chloride, SOCl2.
Two additional products are also produced in this reaction.
i) Give the equation, including state symbols, for the preparation of 1-chloropentane.
[2]
ii) Explain one safety precaution necessary for carrying out this reaction. Justify your
answer.
[2]
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(4 marks)
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2 (a) This question is about the reactions of halogenoalkanes.
2-bromo-2-methylpropane is refluxed with ethanolic potassium hydroxide, KOH. The
result is a mixture of products containing roughly a 4 : 1 ratio of alkene to alcohol.
Complete Table 2.1 to name the organic products and identify the mechanisms involved.
Table 2.1
Organic product Name Mechanism involved
Alkene
Alcohol
(2 marks)
(b) Suggest why there is a mixture of an alkene and an alcohol produced in the reaction
outlined in part (a).
(2 marks)
(c) An iodoalkane is prepared by the reaction of red phosphorus, P, with iodine, I2, to
produce phosphorus(III) iodide, PI3. This then is reacted with an alcohol to produce the
iodoalkane and phosphorous acid, H3PO3.
Give the equation for the reaction between butan-2-ol and phosphorus(III) iodide.
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(2 marks)
(d) During a series of reactions to produce a bromoalkane, a 50 : 50 mix of sulfuric acid and
water is reacted with potassium bromide to produce hydrogen bromide. The mixture is
kept very cool.
Explain why sulfuric acid can not be used in the preparation of an iodoalkane
(1 mark)
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3 (a) Compound G is a chloroalkane that can undergo two different reactions as outlined in
Fig. 3.1.
Fig. 3.1
Compound H is an alkene which does not exhibit geometric isomerism.
Draw the skeletal structures of compounds G and H.
(2 marks)
(b) State the reagents and conditions that will be required for reaction A in Fig. 3.1.
(2 marks)
(c) Name and draw the mechanism for reaction B in Fig 3.1. Include all charges, partial
charges, lone pairs and curly arrows.
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(4 marks)
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4 (a) Bromobutanes react with hot ethanolic potassium hydroxide solution to produce
gaseous butenes.
Procedure
0.0080 mol of liquid 1-bromobutane was injected into a round bottom flask
containing hot ethanolic potassium hydroxide.
After the reaction, the syringe was sealed using a clamp.
The syringe was then removed from the apparatus and allowed to cool to 25oC.
Result
The final volume of but-1-ene collected was 22.0 cm3.
State the purpose of the condenser.
(1 mark)
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(b) Describe a chemical test and the expected observation to identify the functional group of
the gas in the syringe.
(3 marks)
(c) Calculate the percentage of 1-bromobutane which was converted to but-1-ene.
(2 marks)
(d) Before cooling, the volume of but-1-ene in the gas syringe was 24.0 cm3.
Assuming a constant pressure and that no but-1-ene is lost from the gas syringe during
cooling, calculate the temperature of the gas in the syringe.
Temperature = ......................
(2 marks)
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(e) i) Another compound formed from 1-bromobutane under these conditions is butan-1-ol.
Fully identify the type of reaction taking place to form butan-1-ol.
[1]
ii) Draw the mechanism for the reaction of 1-bromobutane with hydroxide ions to form
butan-1-ol. Include all charges, partial charges, lone pairs and curly arrows.
[3]
iii) Describe a chemical test and the expected observation(s) to confirm the presence of
the functional group in butan-1-ol.
[2]
(6 marks)
(f) Isomeric alkene molecules are formed in the elimination reaction of 2-bromobutane.
Draw the displayed formulae of the isomers formed during this reaction.
(3 marks)
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