CHEMISTRY WORKSHEET 1

ORGANIC CHEMISTRY
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28 The ester CH3CH2CH2CO2CH3 is responsible for the aroma of apples.

When this ester is hydrolysed by acid in the stomach, what is the empirical formula of the organic
acid produced?

A CH2O B CH4O C C2H4O D C3H6O2

29 This question should be answered by considering the reactions of KMnO4 with different functional
groups under the stated conditions.

The diagram shows the structure of the naturally-occurring molecule cholesterol.

H 3C
CH3

H
CH3 H

H H
HO
cholesterol

Cholesterol is separately treated with

● cold, dilute acidified KMnO4,

● hot, concentrated acidified KMnO4.

What is the change in the number of chiral carbon atoms in the molecule during each reaction?

cold, dilute acidified hot, concentrated acidified

KMnO4 KMnO4

A +1 0
B +1 –1
C +2 0
D +2 –1

30 Which reaction would not give ethanoic acid as a product?

A heating ethanenitrile under reflux with dilute sodium hydroxide

B heating ethanenitrile under reflux with dilute sulfuric acid
C heating ethanal under reflux with acidified sodium dichromate(VI)
D heating ethanol under reflux with acidified sodium dichromate(VI)

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The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only

are only are only are is
correct correct correct correct

No other combination of statements is used as a correct response.

38 Which compounds when heated under reflux with an excess of hot acidified potassium
dichromate(VI), give a product with a chiral centre?

CH3

1 CH3CH2CCH2OH

CH3

2 CH3CH2CCH2OH

CO2H

CH3

3 CH3COCCH(OH)CH3

CO2CH3

39 In the reaction between an aldehyde and HCN, catalysed by NaCN, which statements about the
reaction mechanism are correct?

1 A new carbon-carbon bond is formed.

2 In the intermediate, the oxygen carries a negative charge.
3 The last stage involves the formation of a hydrogen-oxygen bond.

40 An organic compound, X, will react with an excess of calcium metal to produce a salt with the
empirical formula CaC4H6O4.

What could be the identity of X?

1 ethanoic acid
2 butanedioic acid
3 methylpropanedioic acid

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21 An organic ion containing a carbon atom with a negative charge is called a carbanion.

An organic ion containing a carbon atom with a positive charge is called a carbocation.

The reaction between aqueous sodium hydroxide and 1-bromobutane proceeds by an SN2
mechanism.

What is the first step in the mechanism?

A attack by a nucleophile on a carbon atom with a partial positive charge

B heterolytic bond fission followed by attack by an electrophile on a carbanion
C heterolytic bond fission followed by attack by a nucleophile on a carbocation
D homolytic bond fission followed by attack by a nucleophile on a carbocation

22 Compound X can be converted into compound Y in a single step.

OH
X
O O
Y

What could be the identity of X?

A B C D

23 Which compound reacts with 2,4-dinitrophenylhydrazine reagent but does not react with Tollens’
reagent?

A CH3COCO2H
B CH3CH(OH)CHO
C CH3COCHO
D CH3CH(OH)CH3

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24 Structural isomerism and stereoisomerism should be considered when answering this question.

The molecular formula of compound X is C5H12O.

Compound X:

● reacts with alkaline aqueous iodine

● can be dehydrated to form two alkenes only.

What could be the identity of compound X?

A CH3CH2CH(CH3)CH2OH
B CH3CH2CH(OH)CH2CH3
C (CH3)2CHCH(OH)CH3
D CH3CH2CH2CH(OH)CH3

25 Which volume of hydrogen, measured under room conditions, is produced when 0.160 g of
methanol reacts with an excess of sodium?

A 60 cm3 B 120 cm3 C 240 cm3 D 480 cm3

26 Compound X produces a carboxylic acid when heated under reflux with acidified
potassium dichromate(VI). Compound X does not react with sodium metal.

What could be the identity of compound X?

A propanal
B propanone
C propan-1-ol
D propan-2-ol

27 A reaction occurs when a sample of 1-chloropropane is heated under reflux with

sodium hydroxide dissolved in ethanol.

Which row is correct?

type of reaction name of product

A elimination propan-1-ol
B elimination propene
C substitution propan-1-ol
D substitution propene

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28 Ethanedioic acid has the formula HO2CCO2H.

What is the formula of aluminium ethanedioate?

A Al C2O4 B Al (C2O4)3 C Al 2C2O4 D Al 2(C2O4)3

29 Alcohols, aldehydes and nitriles can each be converted into carboxylic acids.

Which descriptions of their conversions into carboxylic acids are correct?

alcohols aldehydes nitriles

A hydrolysis hydrolysis hydrolysis

B hydrolysis hydrolysis oxidation
C oxidation oxidation hydrolysis
D oxidation oxidation oxidation

30 How many structural isomers with the molecular formula C4H10O give infra-red absorptions both
at approximately 1200 cm–1 and at approximately 3400 cm–1?

A 2 B 4 C 6 D 7

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The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only

are only are only are is
correct correct correct correct

No other combination of statements is used as a correct response.

39 Propanal reacts with hydrogen cyanide to form 2-hydroxybutanenitrile. A suitable catalyst for this
reaction is sodium cyanide.

NaCN
CH3CH2CHO + HCN CH3CH2CH(OH)CN

Which statements about the reaction of propanal with hydrogen cyanide are correct?

1 HCN is a weaker nucleophile than the nucleophile provided by NaCN.

2 The reaction mechanism involves two steps.
3 The product of the reaction has a chiral carbon atom.

40 The structure of lactic acid is shown.

H 3C C
CH OH

OH

lactic acid

Which esters might form when lactic acid is heated?

1 CH3CH(OH)CO2CH(CH3)CO2H

CH3

CH O
O C
2
C O
O CH

CH3

3 CH3CH(OH)CO2CH(OH)CH3

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at
www.cie.org.uk after the live examination series.

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4 Cyclohexaneisacolourlessliquidusedinindustrytoproducesyntheticfibres.

 Areactionschemeinvolvingcyclohexaneisshown.

Cl
reaction 1 reaction 2

(a) Reaction 1involvesafreeradicalsubstitutionmechanism.

(i) Statetheessentialconditionrequiredforreaction1 to occur.

.......................................................................................................................................[1]

(ii) Completethetabletogivedetailsofthemechanisminreaction1.

nameofstep reaction

................................. Cl 2 2Cl •

•
propagation + Cl • +
..............................

Cl
•
................................. + Cl 2 + Cl •

•
termination + Cl •
..............................

 [4]

(b) Namethetypeofreactionthatoccursinreaction2.

..............................................................................................................................................[1]

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(c) The product of reaction 2iscyclohexene.

 Cyclohexenecanbeconvertedintoadipicacid(hexanedioicacid),HO2C(CH2)4CO2H.

(i) Identifythereagentsandconditionsfortheconversionofcyclohexeneintoadipicacid.

.............................................................................................................................................

....................................................................................................................................... [2]

(ii) Suggest three main differences between the infra-red spectra of cyclohexene and
adipic acid.

 In each case, identify the bond responsible and its characteristic absorption range (in
wavenumbers).

 1 ..........................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

2 ..........................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

3 ..........................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................
[3]

 [Total:11]

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3 Crude oil is a natural source of hydrocarbons that are used as fuels.

(a) Hydrocarbons with low relative molecular mass, Mr, are used as fuels in industry, in the home
and for transport.

There is a high demand for the hydrocarbons with low Mr.

(i) Name the process by which long-chain hydrocarbons are broken down into shorter-chain
hydrocarbons.

....................................................................................................................................... [1]

(ii) Give one reason why hydrocarbons with low Mr are suitable for use as fuels.

....................................................................................................................................... [1]

(iii) Incomplete combustion of hydrocarbons can release carbon monoxide, CO, into the
atmosphere.

Write an equation for the formation of CO from the incomplete combustion of butene,
C4H8.

....................................................................................................................................... [1]

(iv) Identify an analytical technique that can be used to monitor the levels of CO in the
atmosphere.

Outline how this analytical technique may be used to monitor the levels of CO.

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [2]

(b) Thiophene, C4H4S(l), is an organic compound that is found as a contaminant in crude oil.

(i) Construct the equation for the complete combustion of thiophene, C4H4S(l).

Include state symbols in your answer.

....................................................................................................................................... [2]

(ii) A student carries out an experiment to determine the enthalpy change of combustion of
C4H4S(l).

Explain the meaning of the term enthalpy change of combustion.

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [2]

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(iii) The student uses the following apparatus in the experiment.

thermometer

copper container

water

fuel burner
containing C4H4S(l)

mass of water in copper container / g 200

initial temperature of water / °C 18.5
highest temperature of water / °C 37.5

Calculate the heat energy released, in J, by the reaction.

Assume that 4.18 J of heat energy changes the temperature of 1.0 cm3 of water by 1.0 °C.

Assume no heat is lost to the surroundings.

heat energy released = .............................. J

[2]

(iv) The student used 0.63 g of C4H4S(l) in the experiment.

Calculate the enthalpy change of combustion of thiophene, ΔHc(C4H4S(l)). Include a sign

in your answer.

 ΔHc(C4H4S(l)) = ............................... kJ mol–1

[2]

[Total: 13]

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4 (CH3)3CCHO is used in the synthesis of some antibiotics.

(a) (i) Give the name of (CH3)3CCHO.

....................................................................................................................................... [1]

(ii) State the hybridisation of the carbon atom labelled with an asterisk, *.

CH3 O
H 3C C C*

CH3 H

....................................................................................................................................... [1]

(b) Two reaction sequences are shown.

CH3 O
NaBH4
H 3C C C S
reaction 3
CH3 H

[O] reaction 1
U

A
T O
(CH3)3CCO2H
reaction 2
O

(i) Reaction 1 is an oxidation reaction.

Identify the reagent(s) and conditions for reaction 1.

....................................................................................................................................... [1]

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(ii) A, (CH3)3CCO2H, is a solid at room temperature.

B, CH3CO2(CH2)2CH3, is an isomer of A. B is a liquid at room temperature.

Explain the difference in the physical states of A and B, with reference to any intermolecular
forces that may exist.

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [3]

(iii) Give the balanced equation for the reaction of (CH3)3CCHO with NaBH4 to form S.

Use [H] to represent an atom of hydrogen provided by NaBH4.

....................................................................................................................................... [1]

(iv) Draw the structure of the organic molecule T that reacts with A, (CH3)3CCO2H, in reaction 2,
to form U.

Suggest a catalyst for reaction 2.

catalyst ...............................................................................................................................
[2]

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(c) X, Y and Z are all isomers of (CH3)3CCHO.

A summary of some of the reactions and properties of X, Y and Z is shown in the table.

observations with principal absorptions

compound observations with 2,4-DNPH
Fehling’s solution in infra-red spectrum

X no reaction 1715 cm–1

Y red precipitate 1730 cm–1

3200–3600 cm–1
Z no reaction no reaction 1630 cm–1
1050 cm–1

(i) X and Y each contains a carbonyl group.

Complete the table with the expected observations for the reactions of X and Y with
2,4-DNPH. [1]

(ii) Identify the functional group present in Y that causes the recorded observation with
Fehling’s solution.

....................................................................................................................................... [1]

(iii) Y has a chiral centre and exists as a pair of optical isomers.

State what is meant by the term chiral centre.

.............................................................................................................................................

....................................................................................................................................... [1]

(iv) Draw the optical isomers of Y using the conventional three-dimensional representation.

[2]

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Z, C5H10O, has a branched carbon chain. It shows geometrical isomerism.

(v) Complete the table with the bond responsible for each of the principal absorptions seen in
the infra-red spectrum of Z.

principal absorptions
bond responsible
in infra-red spectrum

3200–3600 cm–1

1630 cm–1

1050 cm–1
[1]

(vi) Draw the skeletal formula of Z.

[3]

(vii) X contains a carbonyl group. X reacts with HCN, in the presence of a small amount of
NaCN, to form (C2H5)2C(OH)CN as shown.

X + HCN (C2H5)2C(OH)CN

Draw the mechanism of the reaction of X with HCN.

● Draw the structure of X and the intermediate.

● Include all charges, partial charges, lone pairs and curly arrows.

C2 H 5
HO
C
NC
C2 H 5

[3]

(viii) State the role of NaCN in the reaction in (c)(vii).

....................................................................................................................................... [1]

[Total: 22]

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4 Compound S is used in food flavourings. A possible synthesis of S is shown in Fig. 4.1.

P R S

HBr KCN in ethanol H+(aq)

Q
reaction 1 reaction 2 CN reaction 3 COOH

Fig. 4.1

(a) P, Q, R and S show stereoisomerism.

Complete Table 4.1 by identifying with a tick (3) the type of stereoisomerism that each
molecule shows.

The type of stereoisomerism shown by Q is given.

Table 4.1

P Q R S
geometrical
isomerism
optical
3
isomerism
[2]

(b) (i) Give the structural formula of Q.

..................................................................................................................................... [1]

(ii) Name the mechanism in reaction 2.

..................................................................................................................................... [1]

(iii) Complete the equation for reaction 3. R is represented as C4H9CN.

C4H9CN + .................................................................................................................... [1]

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(c) Compounds S and T react to form organic compound U, which has a single functional group.

+ T U + H2 O
COOH

Table 4.2 shows some data from the mass spectrum of U.

Table 4.2

peak relative abundance

M+ 7.2
[M+1]+ 0.55

(i) Use the data from Table 4.2 to show that U contains 7 carbon atoms.

Show your working.

[2]

(ii) Fig. 4.2 shows the infrared spectrum of U.

100

80

60
transmittance / %
40

20

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

Fig. 4.2

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Table 4.3

bond functional groups containing the bond characteristic infrared absorption

range (in wavenumbers) / cm–1
C–O hydroxy, ester 1040–1300
C=C aromatic compound, alkene 1500–1680
C=O amide 1640–1690
carbonyl, carboxyl 1670–1740
ester 1710–1750
C≡N nitrile 2200–2250
C–H alkane 2850–2950
N–H amine, amide 3300–3500
O–H carboxyl 2500–3000
hydroxy 3200–3650

Use Fig. 4.2 and Table 4.3 to identify the functional group present in U.

Explain your answer fully.

functional group .................................................................................................................

explanation ........................................................................................................................

...........................................................................................................................................

...........................................................................................................................................

...........................................................................................................................................
[2]

(iii) T also has a single functional group.

Use the information in (c)(i) and your answer to (c)(ii) to identify T and U.

Draw the structures of T and U in the boxes.

T U

[2]

[Total: 11]

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4 Bromoalkanes are used widely in industry, although there is increasing concern about their
environmental impact.

Fig. 4.1 shows a reaction scheme involving 1,2-dibromoethane.

Br2 Br NaOH(aq)
H2C=CH2 Br

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reaction 1 reaction 2

NaOH in
reaction 3
ethanol

Br polymer C
reaction 4

name .....................................

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an excess of
reaction 5
NaOH in ethanol

HBr, H2O and D

Fig. 4.1

(a) Complete Fig. 4.2 to show the mechanism for the formation of 1,2-dibromoethane in
reaction 1.

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Include charges, dipoles, lone pairs of electrons and curly arrows as appropriate.

H 2C = Br
CH2 Br

Br
Br

Fig. 4.2
[3]
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(b) The enthalpy change of reaction 1, ΔHr = –90.0 kJ mol–1.

Br2
H2C=CH2 Br
reaction 1 Br

The enthalpy change of formation of ethene, ΔHf = +52.2 kJ mol–1.

Calculate the enthalpy change of formation of 1,2-dibromoethane.

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ΔHf of 1,2-dibromoethane = .............................. kJ mol–1 [1]

(c) (i) Complete Fig. 4.1 to:

• draw the structure of compound A

• name compound B.
[2]

(ii) Draw the structure of one repeat unit of polymer C in the box.
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one repeat unit of polymer C

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[1]

(iii) In reaction 5, compound B reacts with an excess of NaOH dissolved in ethanol. The
products are HBr, H2O and an unsaturated hydrocarbon D.

Suggest the identity of D.

..................................................................................................................................... [1]
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(d) Compound E is the only isomer of 1,2-dibromoethane.

Alkaline hydrolysis of E gives compound F.

E F
Br O

Br H

(i) Identify the type of isomerism shown by E and 1,2-dibromoethane.

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..................................................................................................................................... [1]

(ii) Name the homologous series that F belongs to.

..................................................................................................................................... [1]

(iii) Complete Table 4.1 to state what is observed when F reacts with the reagents listed.

Table 4.1

reagent observation with F

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2,4-dinitrophenylhydrazine
(2,4-DNPH reagent)

Tollens’ reagent

alkaline I2(aq)

[3]

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(e) Compound F reacts with reagent G to form compound H.

F
O G
H
H

The infrared spectrum of H is shown in Fig. 4.3.

100

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transmittance / %

50

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0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

Fig. 4.3

Table 4.2

characteristic infrared absorption range

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bond functional groups containing the bond
(in wavenumbers) / cm–1
C–O hydroxy, ester 1040–1300
C=C aromatic compound, alkene 1500–1680
amide 1640–1690
C=O carbonyl, carboxyl 1670–1740
ester 1710–1750
C N nitrile 2200–2250
C–H alkane 2850–2950
N–H amine, amide 3300–3500
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carboxyl 2500–3000
O–H
hydroxy 3200–3600

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15

H also shows a molecular ion peak at m/e = 60 in its mass spectrum.

(i) Use the information in (e), Fig. 4.3 and Table 4.2 to deduce the structure of H. Explain
your answer fully.

H
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...........................................................................................................................................

...........................................................................................................................................

...........................................................................................................................................
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[3]

(ii) Suggest the role of reagent G.

...........................................................................................................................................
[1]

[Total: 17]
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Important values, constants and standards

molar gas constant R = 8.31 J K–1 mol–1

Faraday constant F = 9.65 × 104 C mol–1
Avogadro constant L = 6.022 × 1023 mol–1
e = –1.60 × 10–19 C
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electronic charge
molar volume of gas Vm = 22.4 dm3 mol–1 s.t.p. (101 kPa and 273 K)
Vm = 24.0 dm3 mol–1 at room conditions
ionic product of water Kw = 1.00 × 10–14 mol2 dm–6 (at 298 K (25 °C))
specific heat capacity of water c = 4.18 kJ kg–1 K–1 (4.18 J g–1 K–1)

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