Syllabus Edition

First teaching 2014

Last exams 2024

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Functional Group Chemistry (DP IB Chemistry: SL)

Exam Questions

3 hours51 questions
1a1 mark

A reaction scheme for propene is shown below.

10-2-ib-sl-sq-easy-q1a-reaction-scheme-of-propene

State the condensed structural formula of propene.

1b3 marks

State the IUPAC names for compounds A, B and C shown in the reaction scheme in part (a)

1c3 marks

Propene will also react to form an alcohol. State the reagents and conditions required for the formation of an alcohol from propene. 

1d1 mark

State the colour change when compound B is formed from propene. 

1e2 marks

Propene can form polypropene. Draw the repeating unit that will be formed via the addition polymerisation of propene. 

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2a1 mark

There are three steps to the free radical substitution mechanism. When ethane and chlorine react in the presence of UV light, chloroethane is produced. Write the equation for the initiation step.

2b2 marks

Write two equations for the propagation steps for the reaction outlined in part (a).

2c1 mark

Write the equation using structural formulae for the termination reaction between two CH3CH2 free radicals.

2d1 mark

State the type of bond breaking that occurs in the initiation reaction to produce free radicals. 

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3a4 marks

State the balanced symbol equations for the complete combustion of propane and propanol. 

3b3 marks

The following reaction profile shown produces propanoic acid after three steps.

                  Step 1                   Step 2                     Step 3

Propene         →         Propan-1-ol         →          Propanal       →     Propanoic acid

State the reagents and conditions that can be used for steps 2 and 3. 

3c1 mark

Using your answer to part (b) to state the colour change for step 2.

3d2 marks

Explain why 2-methylpropan-2-ol will not form a carboxylic acid. 

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4a2 marks

Benzene undergoes substitution reactions. State the equation for the reaction of benzene with nitric acid to produce nitrobenzene and water.

4b2 marks

The structure of methylbenzene is shown below.

a2c33069-43fc-46b0-af04-465fc1e6e6d1

Draw the structures of the two isomers of choromethylbenzene formed from the reaction of methyl benzene and Cl2 in the presence of AlCl3

4c1 mark

State the type of reaction that benzene will typically undergo. 

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5a2 marks

The structure of but-1-ene is shown below. But-1-ene IB SL SQ 10.2 E Q5a

Draw and state the name of the secondary halogenoalkane formed when but-1-ene reacts with HCl. 

5b2 marks

Explain why halogenoalaknes are more reactive than alkanes.

5c3 marks

State the reagents and conditions required for the formation of propan-1-ol from 1-bromopropane. 

5d1 mark

The type of reaction outlined in part (c) is nucleophilic substitution. State the meaning of the term nucleophile

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1a2 marks

Ethene, C2H4, can be made into a number of useful compounds. A reaction sequence for this is shown below:

 straight C subscript 2 straight H subscript 4 space rightwards arrow with Step space 1 on top straight C subscript 2 straight H subscript 5 Cl space rightwards arrow with Step space 2 on top straight C subscript 2 straight H subscript 6 straight O space rightwards arrow with Step space 3 on top straight C subscript 2 straight H subscript 4 straight O

i)
Name the type of reaction shown in step 1 

ii)
Write an equation, using structural formulas, for the reaction in step 2 in which C2H5Cl reacts with aqueous NaOH to form C2H6.
1b2 marks

The product of step 2 can undergo combustion.

i)
Write a balanced equation for the complete combustion of the product of step 2. 

ii)
Write a balanced equation for the incomplete combustion of the product of step 2.
1c2 marks

Give the reagents and conditions needed to carry out step 3.

1d3 marks

The product of step 2 has a higher boiling point than the product of step 3.

State the names of the products of step 2 and 3, and explain the difference in their boiling points.

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2a2 marks

Phenylethene, C6H5CH=CH2, is a substance that can be polymerized. Draw a section of the polymer showing three repeat units and name the resulting polymer.

2b4 marks

A solution of bromine in hexane reacts with phenylethene.

i)
Draw the displayed structure of the product. 

ii)
Name the product of the reaction. 

iii)
State the reaction conditions. 

iv)
State what observations would be seen in this reaction. 

2c3 marks

Phenylethene can undergo catalytic hydrogenation. Draw the displayed structure of the product of the reaction, name the product, and state the reaction conditions.

2d3 marks

2-phenylethanol, C6H5CH2CH2OH, is a colourless liquid with a pleasant floral smell widely found in nature. Under the right conditions, it can be made from phenylethene in a two-step reaction using sulfuric acid.

State the reaction conditions and write balanced equations for the two-step reactions.

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3a3 marks

Alkanes are generally unreactive and do not react with acids, bases, or with oxidising or reducing agents. However, they will react with halogens under suitable conditions, to form halogenoalkanes.

Methane reacts with chlorine in this way to form chloromethane.

i)
State the name of this type of reaction mechanism. 

ii)
Write an overall equation for the reaction and give the reaction conditions.  
3b3 marks

The reaction described in part (a) consists of three steps. In the first step, the Cl-Cl bond is broken to form two chlorine free radicals.

i)
State and explain the type of bond breaking that occurs in the initiation step. 

ii)
Define the term free radical

iii)
Explain why the C-H bond in the alkane does not break in the initiation step instead of the Cl-Cl bond. 



3c4 marks

Give the equations for each step of the reaction between methane and chlorine as described in part (a).

Label each equation with the name of the correct step. You only need to provide one equation for the final step.

3d4 marks

Chlorofluorocarbons (CFCs) are organic compounds consisting of carbon, chlorine, and fluorine atoms. They are believed to destroy the ozone layer in a similar reaction to the one described in part (a).

Ozone can be broken down by radicals formed in the atmosphere. The ozone layer is important to protecting the Earth from harmful exposure to ultraviolet light.
Without this ozone layer, life on Earth would be very different.

An example of a CFC which can damage the ozone layer is CCl3F.

i)
Explain why these free radicals act as catalysts in the breakdown of ozone to oxygen. Support your answer by writing suitable equations. 

ii)
Draw the three-dimensional structure of CCl3F and name the shape of the molecule. 

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4a5 marks

Two isomeric compounds are shown below in Figure 1.

 Figure 1

 10-2-ib-chemistry-sq-q4a-medium

i)
State the name of each isomer.

ii)
Suggest a chemical reagent to distinguish between these isomers and deduce the type of reaction taking place.

iii)
State the observations made in each case. 
4b3 marks

Compound B, CH3CH(CH3)CH(OH)COOH, can be oxidized into compound C.

i)
Deduce the half-equation for the conversion of compound B into C. 

ii)

The half equation for the oxidation reaction using acidified potassium dichromate(VI) is as follows:

 Cr2O72- (aq) + 14H+ (aq) + 6e- 2Cr3+ (aq) + 7H2O (l)

 Deduce the overall redox equation for the conversion of B into C.

 

4c2 marks

The same reaction in part (b) can be used to oxidize ethanol into ethanal or ethanoic acid, depending on the reaction conditions.

Outline how the reaction conditions can be changed to produce ethanal or ethanoic acid.

4d3 marks

Under the right conditions, the two molecules of compound A can react together to produce a dimer.

i)
Name the type of reaction taking place and state the reaction conditions. 

ii)
Draw the structure of the product, showing clearly how the two molecules are joined. 

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5a4 marks

Benzene, C6H6, typically undergoes electrophilic substitution

i)
State the meaning of the term electrophile

ii)
Write an equation for the reaction between benzene and concentrated nitric acid. 

iii)
Identify the electrophile in the reaction and show, by means of an equation, how it is generated. 
5b5 marks

Benzene is a highly unsaturated molecule.

i)
Discuss why benzene undergoes substitution reactions rather than addition reactions. 

ii)
Show, by means of an equation, the reaction of benzene with chlorine and state any necessary conditions. 
5c3 marks

An aromatic organic compound with molecular formula C7H8 reacts with bromine in the presence of UV light to produce a compound with molecular formula C7H7

i)
Name the type of reaction taking place.

ii)
Deduce the structures of the reactant and product. 

iii)
Give the formula of an additional organic product that could be obtained in the reaction.
5d3 marks

The same aromatic compound in part (c), C7H8, can be reacted with concentrated  nitric acid to produce a multiple substituted product, with molecular formula C7H5N3O6.

i)
Deduce the systematic IUPAC name for this compound. 

ii)
Draw the structure of C7H5N3O6.
 
iii)
Name a use for the product.

 

 

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1a2 marks

Dichloromethyl benzene reacts with chlorine to produce trichloromethyl benzene. State the name of this type of mechanism and the required condition. 

1b4 marks

Outline the mechanism for the reaction occurring in part a).

1c1 mark

A reaction pathway is shown below. Compound J reacts with bromine water to form a colourless solution.

10-2-ib-sl-sq-hard-q1c-compound-j


State the IUPAC name for Compound J.

1d2 marks

Identify the reagents and conditions for the formation of Compound Y from Compound J. 

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2a
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3 marks

Compounds W, X and Y are all carbohydrates with X and Y each containing five carbons. Compound W and a byproduct, compound Z, are formed from the reaction between compound X and YCompound X can be oxidised by the reaction with acidified potassium dichromate to give compound Y.


2.754 g of compound
Y contains 0.027 moles.


Using the information given, state the name of compound
Y and justify your answer.

2b2 marks

Deduce the structural formula of compound W and explain how compound Z is formed in the reaction.

2c4 marks

Compound X will oxidise to compound Y if allowed to fully oxidise. Explain how a student could stop the full oxidation of compound X

2d1 mark

Deduce the formula of an isomer of compound X that will not react with acidified potassium dichromate, H+ / K2Cr2O7.

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3a2 marks

Ester A is responsible for a raspberry scent and has the molecular formula C5H10O2. Ester A can be produced by the reaction of an acid with a branched primary alcohol. Identify the acid and alcohol used to prepare ester A

3b2 marks

State the IUPAC name and draw the structural formula of ester A.

3c1 mark
State the name of the product when the alcohol used to form ester A reacts with potassium permanganate, KMnO4 (aq).

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4a2 marks

The following scheme shows reactions of Compound A. 

10-2-ib-sl-sq-hard-q4a-reaction-scheme
i)
Deduce the structural formula of compound A.
[1]
ii)
Apply IUPAC rules to name compound B.
[1]
4b2 marks

Reaction 1 forms an alcohol when reacted with concentrated sulfuric acid, H2SOand steam. 

i)
State the conditions required for this reaction.
[1]

ii)
Deduce the structure of the intermediate in this reaction. 
[1]
4c3 marks

Butan-2-ol can also be directly formed from a halogenoalkane. 

i)
State the name of of the type of reaction occurring in this conversation.
[2]
ii)
State the conditions for this reaction. 
[1]
4d1 mark

Identify the structure of the repeating unit of poly(but-2-ene).

4e1 mark

Compound A reacts with hydrogen bromide to form compound C. A student suggested a possible formula of compound C is CH2(Br)CH2CH2CH3.

State whether the student is correct and justify your answer. 

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5a2 marks

A student investigated two reactions of phenylethene, C6H5CHCH2. First she reacted phenylethene with excess bromine at room temperature to form Compound A. She then added aluminium bromide, AlBrto the reaction mixture to form Compound B.

Draw the structure of Compound A and identify one the isomers of C8H7Br3 formed in the second reaction. 

10-2-ib-sl-sq-hard-q5a-reaction-pathway

5b2 marks

2,4,6-trinitrotoluene (TNT) can be manufactured from benzene as shown below.

Chem OCR A2 6.1 Q5c

5.00 g of benzene was used in step 1. Use section 6 of the data booklet to determine the theoretical yield for step 1.

5c3 marks

Step 2 involves the formation of a nitronium ion for the nitration of Toluene, as shown in the following equation:

HNO3 + 2H2SO4 → NO2+ + 2HSO4- + H3O+

i)
Explain the role of the nitric acid in the formation of the electrophile.
[2]
ii)
Explain the role of the sulphuric acid in the overall nitration reaction.
[1]
5d1 mark

Explain why the product of step 2 is most likely to have the nitro group bonded to the second or fourth carbon atom. 

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