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1.

Which of the following statements about alkenes is not correct?


A.

They have reactive double bonds.

B.

They can form addition polymers.

C.

They react mainly by substitution.

D.

They can react with water to form alcohols.


(Total 1 mark)

2.

What is the type of mechanism and an important feature of the reaction between C(CH 3)3Br and
aqueous NaOH?
Mechanism

Feature

A.

SN1

a transition state

B.

SN1

an intermediate

C.

SN2

a transition state

D.

SN2

an intermediate
(Total 1 mark)

3.

Which of the following are isomers of pentane?


I.

2-methylpentane

II.

methylbutane

III.

dimethylpropane

A.

I and II only

B.

I and III only

C.

II and III only

D.

I, II and III
(Total 1 mark)

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4.

Which of the following pairs are members of the same homologous series?
A.

CH3CH2CH2OH and CH3CH2CHO

B.

CH3CH(OH)CH3 and CH3CH2CH(OH)CH3

C.

CH3COCH3 and CH3CH2COOH

D.

CH3COCH2CH3 and CH3CH2CHO


(Total 1 mark)

5.

Alkenes are important starting materials for a variety of products.


(a)

State and explain the trend of the boiling points of the first five members of the alkene
homologous series.
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(3)

(b)

Describe two features of a homologous series.


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(2)
(Total 5 marks)

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6.

Below is a schematic diagram representing some reactions of ethene. The letters AD


represent the organic compounds formed from the reactants and catalysts shown.

Deduce the structural formulas of compounds A, B, C, and D and state the IUPAC
name of compound C.

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A:

B:

C:

IUPAC name: ..............................................................................................................

D:

(Total 5 marks)

7.

Describe a chemical test that could be used to distinguish between pent-1-ene and
pentane.
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(Total 2 marks)

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8.

State and explain whether the following molecules are primary, secondary or tertiary
halogenoalkanes.
E:

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F:

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G:

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(Total 4 marks)

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9.

Explain, using equations, the following steps in the free-radical mechanism of the
reaction of methane with chlorine.

Initiation

Propagation

Termination

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(Total 4 marks)

10.

Which organic molecule is not a structural isomer of pentan-1-ol?


A.

pentan-2-ol

B.

2-methylpentan-2-ol

C.

2-methylbutan-2-ol

D.

pentan-3-ol
(Total 1 mark)

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11.

Which of the structures below is an aldehyde?


A.

CH3CH2CH2CH2OH

B.

CH3CH2COCH3

C.

CH3CH2COOCH3

D.

CH3CH2CH2CHO
(Total 1 mark)

12.

What product is formed when CH3CH(OH)CH3 is reacted with acidified potassium


dichromate(VI)?
A.

CH3COOCH3

B.

CH3CH2CHO

C.

CH3CH2COOH

D.

CH3COCH3
(Total 1 mark)

13.

Which type of reaction occurs when 2-iodo-2-methylpropane, C(CH3)3I, reacts with


aqueous sodium hydroxide, NaOH(aq)?
A.

Addition

B.

Free-radical substitution

C.

S N1

D.

S N2
(Total 1 mark)

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14.

(i)

Describe a chemical test that could be used to distinguish between propane and
propene. In each case state the result of the test.
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(2)

(ii)

Under certain conditions propene can polymerize to form poly(propene). State


the type of polymerization taking place and draw a section of the polymer to
represent the repeating unit.
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(2)

(iii)

Other than polymerization, state one reaction of alkenes which is of economic


importance.
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(1)
(Total 5 marks)

15.

Propan-1-ol and propan-2-ol are two structural isomers of C3H8O.


(i)

State the equation for the complete combustion of C3H8O.


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(2)

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(ii)

Both propan-1-ol and propan-2-ol can be oxidized in aqueous solution by


potassium dichromate(VI). State any necessary conditions for the oxidation to
occur and describe the colour change during the oxidation process.
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(3)

(iii)

State the name(s) and structure(s) of the organic product(s) that can be formed
when each of the alcohols is oxidized and suggest why one of the alcohols gives
two organic products and the other only gives one organic product.
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(5)
(Total 10 marks)

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16.

Which is the best definition of structural isomers?


A.

Compounds which have atoms with the same atomic numbers but different mass
numbers

B.

Compounds which have the same general formula but differ by a CH2 group

C.

Compounds which have the same empirical formula but different molecular
formulas

D.

Compounds which have the same molecular formula but different arrangements
of atoms
(Total 1 mark)

17.

Which is the correct classification of these alcohols?

2
1

3
3

A.

tertiary

secondary

primary

B.

tertiary

primary

secondary

C.

tertiary

tertiary

secondary

D.

secondary

primary

secondary
(Total 1 mark)

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13

18.

Which substances are possible products of the incomplete combustion of octane?


A.

Carbon dioxide and hydrogen gas

B.

Carbon monoxide and water vapour

C.

Carbon monoxide and hydrogen gas

D.

Methane and hydrogen gas


(Total 1 mark)

19.

Which structure could represent a repeating unit of a polymer formed from propene?
A.

( CH2CH(CH3) )

B.

( CH2CH2CH2 )

C.

( CH(CH3)CH(CH3) )

D.

( CH2CH2 )
(Total 1 mark)

20.

Chloroethene, C2H3Cl, is an important organic compound used to manufacture the


polymer poly(chloroethene).
(i)

Draw the Lewis structure for chloroethene and predict the H C Cl bond angle.

.................................................................................................................................
.....
(2)

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14

(ii)

Draw a section of poly(chloroethene) containing six carbon atoms.

(1)

(iii)

Outline why the polymerization of alkenes is of economic importance and why the
disposal of plastics is a problem.
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(2)
(Total 5 marks)

21.

(i)

Chloroethene can be converted to ethanol in two steps. For each step deduce an
overall equation for the reaction taking place.
Step 1:
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Step 2:
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(2)

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(ii)

State the reagents and conditions necessary to prepare ethanoic acid from
ethanol in the laboratory.
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(2)

(iii)

State an equation, including state symbols, for the reaction of ethanoic acid with
water. Identify a Brnsted-Lowry acid in the equation and its conjugate base.
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(3)
(Total 7 marks)

22.

Ethanol is part of the homologous series of alcohols. Describe two features of a


homologous series.
(Total 2 marks)

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23.

(a)

(i)

Below are four structural isomers of alcohols with molecular formula


C4H10O.
State the name of each of the isomers A, B, C and D.

(4)

(ii)

Determine the isomer that cannot be oxidized by acidified potassium


dichromate(VI), K2Cr2O7.
(1)

(iii)

Determine the isomer which can be oxidized to butanal.


(1)

(iv)

Determine the isomer which can be oxidized to butanone.


(1)

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17

(v)

Suggest the structural formula of another isomer of C4H10O.


(1)

(b)

(i)

Isomer A is formed by reacting 1-bromobutane with aqueous sodium


hydroxide.
State whether the reaction would proceed via an SN1 or SN2 mechanism.
(1)

(ii)

Explain the mechanism named in part (b) (i) using curly arrows to represent
the movement of electron pairs.
(3)
(Total 12 marks)

24.

What is the structural formula of 2,3-dibromo-3-methylhexane?


A.

CH3CHBrCHBrCH(CH3)CH2CH3

B.

CH3CHBrCBr(CH3)CH2CH2CH3

C.

CH3CH2CHBrCBr(CH2CH3)2

D.

CH3CHBrCHBrCH(CH2CH3)2
(Total 1 mark)

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25.

What happens when a few drops of bromine water are added to excess hex-1-ene and
the mixture is shaken?
I.

The colour of the bromine water disappears.

II.

The organic product formed does not contain any carbon-carbon double
bonds.

III.

2-bromohexane is formed.

A.

I and II only

B.

I and III only

C.

II and III only

D.

I, II and III
(Total 1 mark)

26.

What is the product of the following reaction?


2

Cr2 O 7 /H
CH3CH(OH)CH3

A.

CH3COOH

B.

CH3COCH3

C.

CH3CH2COOH

D.

CH3CH2CH3
(Total 1 mark)

27.

Alkenes are an economically and chemically important family of organic compounds.


(i)

The reaction of alkenes with bromine water provides a test for unsaturation in the
laboratory. Describe the colour change when bromine water is added to
chloroethene.
(1)

(ii)

Deduce the Lewis structure of chloroethene and identify the formula of the
repeating unit of the polymer poly(chloroethene).
(2)

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(iii)

Besides polymerization, state two commercial uses of the reactions of alkenes.


(2)
(Total 5 marks)

28.

But-2-ene can be converted to butan-2-one in two stages.


(i)

Draw the structural formulas of but-2-ene and butan-2-one.


(2)

(ii)

Deduce a reaction pathway for the two stages of the reaction. Your answer
should include the fully balanced equation for each stage of the reaction and the
reagents and conditions for the two stages.
(5)
(Total 7 marks)

29.

(i)

Deduce the structural formulas of the two alcohol isomers of molecular formula
C3H8O. Name each isomer and identify each as either a primary or a secondary
alcohol.
(3)

(ii)

Oxidation of the alcohol isomers lead to the formation of different organic


products.
Determine the structures of the organic products formed from the oxidation of
each alcohol isomer in (i) above and list the conditions required to obtain the
different products.
(5)
(Total 8 marks)

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30.

Which of the following substances are structural isomers of each other?


I.

CH3(CH2)3CH3

II.

(CH3)2CHCH3

III.

CH3CH(CH3)CH2CH3

A.

I and II only

B.

I and III only

C.

II and III only

D.

I, II and III
(Total 1 mark)

31.

Which order is correct when the following substances are arranged in order of
increasing boiling point?
A.

CH3CH3 < CH3CHO < CH3CH2OH

B.

CH3CHO < CH3CH2OH < CH3CH3

C.

CH3CH2OH < CH3CH3 < CH3CHO

D.

CH3CH3 < CH3CH2OH < CH3CHO


(Total 1 mark)

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32.

Which monomer could be used to form a polymer with the following repeating unit?

A.

CH3CH2Cl

B.

CH2ClCH2Cl

C.

CH2CHCl

D.

CHClCHCl
(Total 1 mark)

33.

Which reaction pathway describes how ethanol can be formed?


A.

addition
elimination
ethene chloroethane ethanol

B.

substitution
nucleophilic substitution
ethane chloroethane ethanol

C.

substitution
ethene ethanol

D.

addition
ethane ethanol

(Total 1 mark)

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34.

The alkenes are an example of a homologous series.


(a)

State the name of the alkene shown.

.................................................................................................................................
.....
(1)

(b)

Bromine water, Br2(aq), can be used to distinguish between the alkanes and the
alkenes.
(i)

Describe the colour change observed when the alkene shown in part (a) is
added to bromine water.
........................................................................................................................
...
........................................................................................................................
...
(1)

(ii)

Draw the structural formula and state the name of the product formed.

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...
(2)
(Total 4 marks)

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35.

The polymerization of the alkenes is one of the most significant reactions of the
twentieth century.
(i)

Outline two reasons why the polymers of the alkenes are of economic
importance.
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(2)

(ii)

State the type of polymerization reaction shown by the alkene below.

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(1)

(iii)

Deduce the structure of the resulting polymer showing three repeating units.

(1)

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(iv)

Explain why monomers are often gases or volatile liquids, but polymers are
solids.
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(2)
(Total 6 marks)

36.

State the name of the product and identify the type of reaction which occurs between
ethene and hydrogen chloride.
(Total 2 marks)

37.

Consider the following sequence of reactions.


reaction 1
reaction 2
reaction 3
RCH3 RCH2Br RCH2OH RCOOH

RCH3 is an unknown alkane in which R represents an alkyl group.

(a)

The alkane contains 81.7 % by mass of carbon. Determine its empirical formula,
showing your working.
(3)

(b)

Equal volumes of carbon dioxide and the unknown alkane are found to have the
same mass, measured to an accuracy of two significant figures, at the same
temperature and pressure. Deduce the molecular formula of the alkane.
(1)

(c)

(i)

State the reagent and conditions needed for reaction 1.


(2)

(ii)

State the reagent(s) and conditions needed for reaction 3.

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(2)

(d)

Reaction 1 involves a free-radical mechanism. Describe the stepwise


mechanism, by giving equations to represent the initiation, propagation and
termination steps.
(4)

(e)

The mechanism in reaction 2 is described as SN2.


(i)

State the meaning of each of the symbols in SN2.


(1)

(ii)

Explain the mechanism of this reaction using curly arrows to show the
movement of electron pairs, and draw the structure of the transition state.
(3)
(Total 16 marks)

38.

Propan-1-ol has two structural isomers.


(i)

Deduce the structural formula of each isomer.


(2)

(ii)

Identify the isomer from part (i) which has the higher boiling point and explain
your choice. Refer to both isomers in your explanation.
(2)
(Total 4 marks)

39.

Which three compounds can be considered to be a homologous series?


A.

CH3OH,

CH3CH2OH,

CH3CH2CH2OH

B.

CH3CH2OH,

C.

CH3CH2CH(OH)CH3,

CH3CH2CH2CH2OH,

D.

CH3CH2CH2CH2OH,

CH3CH2OCH2CH3,

CH3CHO,

CH3COOH
(CH3)3COH
(CH3)2CH2CHO
(Total 1 mark)

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40.

What is the IUPAC name for CH3CH2CH(CH3)CH3?


A.

1,1-dimethylpropane

B.

2-ethylpropane

C.

2-methylbutane

D.

3-methylbutane
(Total 1 mark)

41.

When bromine water is shaken with a liquid organic compound, it is rapidly


decolorized. What can be determined from this test?
A.

The compound is an alcohol.

B.

The compound is an alkane.

C.

The compound is an alkene.

D.

The compound is an iodoalkane.


(Total 1 mark)

42.

Which conditions are required to obtain a good yield of a carboxylic acid when ethanol
is oxidized using potassium dichromate(VI), K2Cr2O7(aq)?
I.

Add sulfuric acid

II.

Heat the reaction mixture under reflux

III.

Distil the product as the oxidizing agent is added

A.

I and II only

B.

I and III only

C.

II and III only

D.

I, II and III
(Total 1 mark)

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43.

Three compounds with similar relative molecular masses are butane, propanal and
propan-1-ol.
(i)

List the three compounds in order of increasing boiling point (lowest first) and
explain the differences in their boiling points.
(4)

(ii)

Predict, with an explanation, which of the three compounds is least soluble or


miscible in water.
(2)

(iii)

When propan-1-ol is oxidized using a warm acidified solution of potassium


dichromate(VI) two different organic products can be obtained. Deduce the name
and structural formula for each of these two products.
(3)

(iv)

Propan-2-ol is an isomer of propan-1-ol. Draw the structure of propan-2-ol.


(1)

(v)

Identify the class of alcohols that propan-2-ol belongs to and state the name of
the organic product formed when it is oxidized by an acidified solution of
potassium dichromate(VI).
(2)
(Total 12 marks)

44.

Ethanol can be formed from ethene in a two step reaction:

(i)

State the name of the reagent used for step 1.


(1)

(ii)

State the name of the reagent and the conditions used for step 2.
(2)

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28

(iii)

The mechanism involved in step 2 is SN2. Explain how the reaction proceeds
using curly arrows to represent the movement of electron pairs.
(3)

(iv)

Outline how ethanol is manufactured from ethene in industry and state one
important commercial use of ethanol.
(2)
(Total 8 marks)

45.

What is the product of the oxidation of butan-2-ol?


A.

But-2-ene

B.

Butanoic acid

C.

Butanal

D.

Butanone
(Total 1 mark)

46.

Which is a tertiary halogenoalkane?


A.

CH3CH2CH2Br

B.

CH3CH2CH(CH3)Cl

C.

C(CH3)3Br

D.

CH3CHClCH2CH3
(Total 1 mark)

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47.

What is the IUPAC name of the following compound?

A.

2-methylbutane

B.

Ethylpropane

C.

3-methylbutane

D.

Pentane
(Total 1 mark)

48.

Which equations represent the incomplete combustion of methane?


I.

CH4(g) + 2O2(g) CO2(g) + 2H2O(g)

II.

CH4(g) + 1O2(g) CO(g) + 2H2O(g)

III.

CH4(g) + O2(g) C(s) + 2H2O(g)

A.

I and II only

B.

I and III only

C.

II and III only

D.

I, II and III
(Total 1 mark)

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30

49.

In some countries, ethanol is mixed with gasoline (petrol) to produce a fuel for cars
called gasohol.
(i)

Define the term average bond enthalpy.


(2)

(ii)

Use the information from Table 10 of the Data Booklet to determine the standard
enthalpy change for the complete combustion of ethanol.
CH3CH2OH(g) + 3O2(g) 2CO2(g) + 3H2O(g)
(3)

(iii)

The standard enthalpy change for the complete combustion of octane, C8H18, is
1

5471 kJ mol . Calculate the amount of energy produced in kJ when 1 g of


ethanol and 1 g of octane is burned completely in air.
(2)

(iv)

Ethanol can be oxidized using acidified potassium dichromate, K2Cr2O7, to form


two different organic products.
CH3CH2OH

State the structural formulas of the organic products A and B and describe the
conditions required to obtain a high yield of each of them.
(4)

(v)

Deduce and explain whether ethanol or A has the higher boiling point.
(2)

(vi)

Ethene can be converted into ethanol by direct hydration in the presence of a


catalyst according to the following equation.
C2H4(g) + H2O(g)

CH3CH2OH(g)

For this reaction identify the catalyst used and state one use of the ethanol
formed other than as a fuel.
(2)
(Total 15 marks)

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31

50.

(i)

State the name of one structural isomer of pentane.


(1)

(ii)

Sodium hydroxide reacts with 1-bromopentane via an SN2 mechanism.


Describe the mechanism of this reaction using curly arrows to represent the
movement of electron pairs.
(4)
(Total 5 marks)

51.

How many structural isomers exist with the formula C3H5Cl3?


A.

B.

C.

D.

6
(Total 1 mark)

52.

Which substance is produced by the reaction of hydrogen with a vegetable oil?


A.

Margarine

B.

Nylon

C.

Polypropene

D.

Soap
(Total 1 mark)

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32

53.

Which substance is not produced during the combustion of alkanes?


A.

CO2

B.

CO

C.

D.

H2
(Total 1 mark)

54.

Propene is converted to propanone in a two stage process.


Propene X Propanone
What is the formula of compound X?
A.

CH3CHBrCH3

B.

CH3CH2CH2Br

C.

CH3CHOHCH3

D.

CH3CH2CH2OH
(Total 1 mark)

55.

(a)

The boiling points of the isomers of pentane, C5H12, shown are 10, 28 and 36 C,
but not necessarily in that order.

IB Questionbank Chemistry

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(i)

Identify the boiling points for each of the isomers A, B and C and state a
reason for your answer.
Isomer

Boiling point
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...
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...
(3)

(ii)

State the IUPAC names of isomers B and C.


B: ...................................................................................................................
....
C: ...................................................................................................................
....
(2)

(b)

Both C5H12 and C5H11OH can be used as fuels. Predict which compound would
release a greater amount of heat per gram when it undergoes complete
combustion. Suggest two reasons to support your prediction.
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(3)
(Total 8 marks)

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56.

Halogenoalkanes can undergo substitution reactions with potassium hydroxide


solution.
(i)

State an equation for the reaction of C4H9Cl with KOH.


(1)

IB Questionbank Chemistry

35

(ii)

Substitution reactions may occur by either of two mechanisms namely SN1 or


SN2.
Outline the meaning of the term SN1.
(2)

(iii)

Predict the mechanism (SN1 or SN2) expected for the reaction of the following
halogenoalkanes with aqueous KOH.
1-chlorobutane to form butan-1-ol
2-chloro-2-methylpropane to form 2 methylpropan-2-ol.
(2)

(iv)

Explain the mechanism of each reaction in part (iii) using curly arrows to
represent the movement of electron pairs.
(6)
(Total 11 marks)

57.

(i)

Draw four structural isomers of molecular formula C4H10O which contain the OH
group.
(4)

(ii)

On reaction with acidified potassium dichromate(VII), two of the isomers are


oxidized in two steps to produce different products. Draw the structural formula of
the two products formed from one of the isomers.
(2)

(iii)

A third isomer is oxidized in one step. Draw the structural formula of the organic
product formed.
(1)

(iv)

State the colour change that takes place in these oxidation reactions.
(1)

(v)

Identify the isomer which resists oxidation by acidified potassium dichromate(VI).


(1)
(Total 9 marks)

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36

58.

Which statement about successive members of all homologous series is correct?


A.

They have the same empirical formula.

B.

They differ by a CH2 group.

C.

They have the same physical properties.

D.

They differ in their degree of unsaturation.


(Total 1 mark)

59.

The following is a three-dimensional representation of an organic molecule.

IB Questionbank Chemistry

37

Which statement is correct?


A.

The correct IUPAC name of the molecule is 2-methylpentane.

B.

All the bond angles will be approximately 90.

C.

One isomer of this molecule is pentane.

D.

The boiling point of this compound would be higher than that of pentane.
(Total 1 mark)

60.

Which compound forms when hydrogen bromide is added to but-2-ene?


A.

2-bromobutane

B.

2,3-dibromobutane

C.

1-bromobutane

D.

1,2-dibromobutane
(Total 1 mark)

61.

Which products can be potentially obtained from crude oil and are economically
important?
I.
II.
III.

Plastics
Margarine
Motor fuel

A.

I and II only

B.

I and III only

C.

II and III only

D.

I, II and III
(Total 1 mark)

IB Questionbank Chemistry

38

62.

Propane, C3H8, undergoes incomplete combustion in a limited amount of air. Which


products are most likely to be formed during this reaction?
A.

Carbon monoxide and water

B.

Carbon monoxide and hydrogen

C.

Carbon dioxide and hydrogen

D.

Carbon dioxide and water


(Total 1 mark)

63.

(a)

List two characteristics of a homologous series.


.................................................................................................................................
....
.................................................................................................................................
....
.................................................................................................................................
....
(1)

(b)

Ethanol and ethanoic acid can be distinguished by their melting points. State and
explain which of the two compounds will have a higher melting point.
.................................................................................................................................
....
.................................................................................................................................
....
.................................................................................................................................
....
.................................................................................................................................
....
(2)

IB Questionbank Chemistry

39

(c)

Draw the three isomers containing the alcohol functional group of formula
C4H9OH.

(2)
(Total 5 marks)

IB Questionbank Chemistry

40

64.

The following is a computer-generated representation of the molecule, methyl 2hydroxy benzoate, better known as oil of wintergreen.

(i)

Deduce the empirical formula of methyl 2-hydroxy benzoate and draw the full
structural formula, including any multiple bonds that may be present.
The computer-generated representation shown does not distinguish between
single and multiple bonds.
(2)

(ii)

In this representation, two of the carbon-oxygen bond lengths shown are 0.1424
nm and 0.1373 nm. Explain why these are different and predict the carbonoxygen bond length in carbon dioxide.
(2)

(iii)

Name all the functional groups present in the molecule.


(2)
(Total 6 marks)

IB Questionbank Chemistry

41

65.

(i)

State and explain the trend in the boiling points of the first six alkanes involving
straight-chains.
(2)

(ii)

Write an equation for the reaction between methane and chlorine to form
chloromethane. Explain this reaction in terms of a free-radical mechanism.
(5)
(Total 7 marks)

66.

(i)

Identify the formulas of the organic products, AE, formed in the reactions, IIV:

I.

H
CH3(CH2)8OH + K2Cr2O7 A

II.

(CH3)3CBr + NaOH C

III.

(CH3)2CHOH + K2Cr2O7

IV.

H2C=CH2 + Br2 E

(5)

(ii)

H2C=CH2 can react to form a polymer. Name this type of polymer and draw the
structural formula of a section of this polymer consisting of three repeating units.
(2)
(Total 7 marks)

IB Questionbank Chemistry

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