12.

Which of the following reacts with hydrogen cyanide, HCN, to make a racemic mixture?
A

Methanal, HCHO

Ethanal, CH3CHO

Propanone, CH3COCH3

Pentan-3-one, C2H5COC2H5
(Total 1 mark)

13.

Which of the following is a redox reaction?

A

Ethanal reacting with Tollens reagent.

Ethanoyl chloride reacting with ammonia.

Ethanoic acid reacting with ethanol.

Ethanoic acid reacting with sodium hydroxide.

(Total 1 mark)

14.

16.

The following methods can be used to distinguish between pairs of organic compounds without further tests.
A

Warm each compound with Fehlings or Benedicts solution.

Add solid sodium carbonate to each compound.

Add 2,4-dinitrophenylhydrazine (Bradys reagent) to each compound.

Add water, drop by drop, to each compound.

When the following reaction mixtures are warmed, which will contain ethanoic acid as one of the products?
A

Ethyl methanoate and sodium hydroxide solution.

Ethyl methanoate and dilute sulfuric acid.

Methyl ethanoate and sodium hydroxide solution.

Methyl ethanoate and dilute sulfuric acid.

(Total 1 mark)

19.

This question is about butanoic acid, CH3CH2CH2COOH.

(a)

Some reactions involving butanoic acid are shown below.

(i)

What type of reaction is Reaction A?

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

(ii)

Identify, by name or formula, the reagent which is used with sulfuric acid to carry out Reaction
B.
...........................................................................................................................
(1)

(iii)

What reagent is used in Reaction C?

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

(iv)

Name the organic product of Reaction D and write a balanced equation for its formation.
Name...................................................................................................................
Equation
(2)

(v)

Write the displayed formula for Z, the organic product of the reaction of butanoic acid with
phosphorus(V) chloride, PCl5
(1)

(b)

Butanoic acid and propane-1,2,3-triol are formed when fats in milk are hydrolysed. The presence of
milk fat in low fat spreads is detected by hydrolysing the spread, and then analysing the products using
gas chromatography (also called gas-liquid chromatography, GLC).
(i)

Explain why nitrogen, rather than oxygen, is used as the carrier gas in GLC.
...........................................................................................................................
...........................................................................................................................
(1)

(ii)

What property determines whether butanoic acid or propane-1,2,3-triol would move faster

through the chromatography column?

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

(c)

The formula of 3-hydroxybutanoic acid is shown below.

(i)

3-hydroxybutanoic acid can form a polymer which is used to make green packaging as it is
biodegradable.
Draw a section of this polymer, showing TWO monomer units. Clearly show any double bonds.
(2)

(ii)

The polymer cannot be used in acidic conditions. What reaction would occur when the polymer
is in prolonged contact with an acid?
...........................................................................................................................
...........................................................................................................................
(1)
(Total 11 marks)

20.

Ethanoic acid can be manufactured by the following reaction, which is carried out between
150 C and 200 C.
CH3OH(g) + CO(g)
(a)

CH3COOH(g)

A mixture of 50.0 mol of methanol and 50.0 mol of carbon monoxide reaches equilibrium at a
pressure of 32.0 atm. At 175 C, the equilibrium partial pressure of ethanoic acid is 22.2 atm.
(i)

Write the expression for the equilibrium constant in terms of pressure, Kp, for this reaction.
(1)

(ii)

Calculate the partial pressures of methanol and carbon monoxide at equilibrium.

Methanol...............................................................................................
Carbon monoxide................................................................................
(2)

(iii)

Calculate the value of Kp for this reaction at 175 C. Include a unit in your answer and give
your answer to three significant figures.
(2)

(b)

Another sample of 50.0 mol of methanol and 50.0 mol of carbon monoxide was allowed to reach
equilibrium at the same pressure of 32.0 atm, but at a lower temperature. 93.6% of the methanol was

converted at equilibrium.
(i)

Complete the table below to show the number of moles of each species in the equilibrium
mixture.

Number of moles at
start

CH3OH

CO

CH3COOH

50.0

50.0

Number of moles at
equilibrium
(2)

(ii)

Calculate the partial pressure of ethanoic acid in the equilibrium mixture.

(1)

(iii)

Is the reaction exothermic or endothermic? Explain your answer.

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

(c)

How, if at all, does the addition of methanol to the equilibrium mixture affect the following? Justify
your answers.
CH3OH(g) + CO(g)
(i)

CH3COOH(g)

The equilibrium constant for the formation of ethanoic acid.

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

(ii)

The equilibrium yield of ethanoic acid.

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

(d)

In industry, catalysts are used even though they are often expensive.
State and explain ONE benefit to the environment resulting from the use of catalysts in industrial
processes.

.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)
(Total 13 marks)

41.

Which of the following molecules is a methyl ester?

A

CH3COOCH2CH3

HCOOCH3

CH3COCH2CH3

CH3COCl
(Total 1 mark)

43.

Which of the following compounds would react with lithium tetrahydridoaluminate (lithium aluminium
hydride) and also with phosphorus(V) chloride (phosphorus pentachloride)?
A

CH3CH2CH2COOH

CH3CH2COCH3

CH3CH==CHCH3

CH2==CHCH2CH2OH
(Total 1 mark)

44.

In the synthesis of an ester, the use of an acyl chloride and an alcohol gives a better yield than the use of a
carboxylic acid and an alcohol.
This is because the reaction between
A

an acyl chloride and an alcohol is an equilibrium.

an acid and an alcohol goes to completion.

an acid and an alcohol requires a catalyst.

an acyl chloride and an alcohol goes to completion.

(Total 1 mark)

46.

Which of the following methods may be used in a single step to make carboxylic acids?
A

Hydrolysis of an ester with an alkali.

Reaction of acidified potassium manganate(VII) with an alkene.

Hydrolysis of a nitrile with hydrochloric acid.

Reaction of an acyl chloride with ammonia.

(Total 1 mark)

49.

(a)

Ethanol can be oxidized successively to ethanal and to ethanoic acid.

The boiling temperatures of these substances are:
ethanol 78 C, ethanal 21C, ethanoic acid 118 C.
Explain in terms of the intermolecular forces in the liquids why the order of the boiling temperature is
ethanal < ethanol < ethanoic acid
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(3)

(b)

State what tests you would perform in each case, and the result you would expect, to show that
(i)

ethanal contains a carbonyl group.

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

(ii)

ethanal is an aldehyde.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(c)

Ethanal reacts with HCN, in the presence of a catalyst of cyanide ions from KCN, to give a
cyanohydrin, CH3CH(OH)CN.
(i)

Give the mechanism for this reaction.

(3)

(ii)

Explain why it is necessary to use HCN and KCN in this reaction, rather than HCN on its own.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(1)

(iii)

Explain why the product mixture from this reaction is not optically active.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)
(Total 13 marks)

55.

Propanone, C3H6O, undergoes complete combustion to form carbon dioxide and water.
C3H6O(l) + 4O2(g) 3CO2(g) + 3H2O(l)
(a)

In an experiment to calculate the enthalpy change of combustion for propanone, 2.90 g of propanone
was burned completely in oxygen.
The heat energy from this combustion raised the temperature of 200 g of water from 20.2 C to 78.4
C.
The specific heat capacity of water is 4.18 J g1C1.
(i)

Calculate the number of moles of propanone present in 2.90 g.

[The molar mass of propanone is 58 g mol1.]

(1)

(ii)

Use the expression

energy transferred (J) = mass

temperatur e
specific heat

change
capacity

to calculate the heat energy transferred to raise the temperature of 200 g of water from 20.2 C
to 78.4 C.
(2)

(iii)

Use your answers to (a)(i) and (ii) to calculate a value for the enthalpy change of combustion of
propanone. Give your answer to three significant figures and include a sign and units.
(3)

(b)

In another experiment, the enthalpy change of combustion for butanone, C4H8O, was found to be
1300 kJ mol1.
A Data Book value for the standard enthalpy change of combustion for butanone is 2440 kJ mol1.
(i)

Suggest a reason why the value obtained in the experiment is so different from the Data Book
value.
...............................................................................................................
(1)

(ii)

This Data Book value (2440 kJ mol1) refers to the following equation.
C4H8O(l) +

11

O2(g) 4CO2(g) + 4H2O(l)

How would the value be different if it referred to the formation of water in the gaseous state?
Justify your answer.
Difference.........................................................................................................
Justification.......................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(c)

Standard enthalpy changes of combustion can be used to calculate the standard enthalpy change of
formation of a compound.
(i)

Define the term standard enthalpy change of formation, making clear the meaning of
standard in this context.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(3)

(ii)

Use the standard enthalpy changes of combustion, Hc, given in the table below to find the
standard enthalpy change of formation for ethanoic acid, CH3COOH, in kJ mol1.
Substance

Hc
/ kJ mol1

C(s, graphite)

394

H2(g)

286

CH3COOH(l)

870

2C(s, graphite) + 2H2(g) + O2(g) CH3COOH(l)

(3)
(Total 15 marks)

57.

Which of the following values for the mass/charge ratio for singly charged ions would be present in the mass
spectrum of propanal, CH3CH2CHO, but not of propanone, CH3COCH3?
A

15

29

43

58
(Total 1 mark)

(b)

Propanone, CH3COCH3, is a useful solvent for cleaning glassware in laboratories.

(i)

Why is propanone able to dissolve a wide range of substances?

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

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

(ii)

Propanone can be used to remove both water and octane from glassware. For each of these
substances, identify the strongest intermolecular force formed with propanone and the feature of
the propanone molecule involved.
Water................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
Octane...............................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)
(Total 8 marks)

(b)

Which of the following best represents the first step of the mechanism for this reaction with an
aldehyde?
R
A

R
C

C+

C
H

O
N:)

R
C

C
H

CN

(:C

O
C

(:C

N:)

R
H

CN

R
C

O H

C N

OH
C+

+ CN

H
(1)
(Total 2 marks)

110. Ethanal, CH3CHO, can be converted into 2-hydroxypropanoic acid, CH3CH(OH)COOH.

State the reagents and conditions needed for each step in this synthesis.
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
(Total 4 marks)

111. Cyanide ions react with 2-bromo-2-methylpropane in the following way:

(CH3)3CBr + CN (CH3)3CCN + Br
The rate equation for this reaction is
rate = k[(CH3)3CBr]

(i)

What information does this rate equation give about the mechanism of this reaction?
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)

(ii)

Give the mechanism for this reaction consistent with the rate equation.

(3)

114. (a)

Name the homologous series to which the compound CH3CH2CHO belongs.

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

(b)

Describe what you would see if a sample of CH3CH2CHO was warmed with Benedicts solution.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)

123. Consider the following compounds.

H H H
Compound X

HCCCC

H H H

OCH
H

H
C

Compound Y
H

CCH
OH H

H
Compound Z

HCCCC
OH H

(a)

Name the functional groups present in the three compounds X, Y and Z.

Compound

Functional groups present

Z
(3)

125. Name the following organic compound

HCHO
...............................................................................................................................................
(Total 1 mark)

126. (a)

Draw the displayed formula of a branched chain ketone containing five carbon atoms.

(2)

(b)

Give the systematic name for this ketone.

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

(c)

What is the molecular formula of the alcohol this ketone could be made from?
.....................................................................................................................................
(1)

(d)

An alcohol can be converted into a ketone by oxidation with sodium dichromate(VI) and sulphuric
acid.
Explain why refluxing the mixture first, rather than immediately distilling the product over from the
beginning, results in a higher yield of the ketone.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(1)
(Total 5 marks)

132. Methanoic acid and ethanol react together to form ethyl methanoate, HCOOC2H5, and water. This reaction is
reversible and can be allowed to reach equilibrium.
HCOOH(l) + C2H5OH(l)
(a)

HCOOC2H5 (l) + H2O(l)

H = +45 kJ mol1

Draw the full structural formula of ethyl methanoate, showing all bonds.

(1)

(b)

What type of organic compound is ethyl methanoate?

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

(c)

In an experiment, 3.00 mol methanoic acid, HCOOH, and 6.25 mol ethanol, C2H5OH, were mixed
together. A small quantity of catalyst was added. The mixture was left for several days in a water bath
to reach equilibrium at constant temperature.
(i)

Complete the table.

Number of moles in the reaction mixture

HCOOH

C2H5OH

HCOOC2H5

H2O

at start of
experiment

3.00

6.25

0.00

0.00

at equilibrium

0.50
(2)

(ii)

Write an expression for the equilibrium constant, Kc, for the reaction.

(1)

(iii)

Calculate Kc for the reaction at the temperature of the experiment. The total volume of the
equilibrium mixture was 485 cm3.

(2)

(iv)

State and explain whether Kc for this reaction has units.

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

(d)

(i)

The temperature of this equilibrium mixture is lowered.

Explain the effect of this on the value of the equilibrium constant and hence on the yield of
ethyl methanoate.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................

...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(4)

(ii)

A student added more catalyst to the mixture.

State, giving a reason, what would happen to the composition of the equilibrium mixture.
...........................................................................................................................
...........................................................................................................................
(1)
(Total 13 marks)

148. This question is about butanal, CH3CH2CH2CHO, and several related compounds.
(a)

What would you see when Bradys reagent is added to a sample of butanal?
.....................................................................................................................................
(1)

(b)

F, G and H are three isomers of butanal which are each tested with sodium, Benedicts reagent and
Bradys reagent. The results are shown in the table below.
Key:

= positive result
= negative result
Sodium

Benedicts reagent

F
G
H
Suggest structural formulae for F, G and H.

Bradys reagent

(3)

(c)

An ester with the formula, CH3CH2CH2CO2CH2CH3, is heated under reflux with aqueous sodium
hydroxide.
(i)

Give ONE advantage of heating under reflux, rather than simply boiling the two liquids
together in a beaker.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(1)

(ii)

Name the ester.

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

(iii)

Name the TWO products of this reaction.

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

(iv)

What type of reaction is taking place?

...........................................................................................................................
(1)
(Total 9 marks)

153. The structural formula of the compound propenal is shown below.

O
C
H

In this question, assume that the functional groups in the molecule behave independently.

(a)

(i)

State what is observed when propenal reacts with 2,4-dinitrophenylhydrazine.

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

(ii)

Give the structural formula of the compound formed in the reaction in (a)(i).

(2)

(b)

Explain why propenal has three peaks in its low-resolution n.m.r. spectrum. Suggest the relative areas
under these peaks.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(3)

(c)

Propenal reacts with hydrogen cyanide as shown by the following equation

CH2
(i)

CHCHO + HCN

Write the mechanism for the reaction.

CH2

CHCH(OH)CN

(4)

(ii)

Name the type of mechanism involved in this reaction.

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

(d)

Propenal reacts with hydrogen bromide as shown by the following equation

CH2
(i)

CHCHO + HBr

CH3CHBrCHO

Write the mechanism for the reaction.

(3)

(ii)

Name the type of mechanism involved in this reaction.

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

(e)

The C O and C C bonds have the same electronic structure but their reactions occur by different
mechanisms. Explain why this is so.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(3)
(Total 18 marks)

159. For each of the following reactions, give the names of all of the organic products.
Also give the type or mechanism as indicated for each reaction,
(a)

CH3CO2H + NaOH CH3CO2Na + H2O

Name of organic product ..........................................................................................
Type of reaction

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

(b)
O

CH3

O
+ ICl

CH3
+ HCl

Name of organic product

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

Type of reaction

......substitution...............................................................

Mechanism

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

(c)

CH3COCl + 2NH3 CH3CONH2 + NH4Cl

Name of organic product

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

Type of reaction

......substitution...............................................................

Mechanism

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

(d)

CH2OCO(CH2)8CH3

CHOCO(CH2)8CH3

CH2OCO(CH2)8CH3
Names of products

CH2OH

H (aq)

+ 3H2O

CHOH + 3CH3(CH2)8CO2H

CH2OH

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

Type of reaction

.........................................................................................
(3)
(Total 9 marks)

160. This question is about a compound, A, used as a food flavouring. It has the molecular formula, C9H8O.
(a)

For each of the following pieces of information, state what can be deduced about the a structure of A.
(i)

A burns with a very sooty flame.

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

(ii)

A reacts with Bradys Reagent (2,4-dinitrophenylhydrazine) to give an orange precipitate.

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

(iii)

When A is heated with Benedicts solution, a red precipitate forms.

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

(iv)

A decolorises bromine water.

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

(v)

A is the cis isomer.

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

(vi)

Use all of the above information to draw the displayed formula of A.

(2)

(b)

Compound A can be converted to benzoic acid, C6H5CO2H, which is formed as a white precipitate.
(i)

The precipitate can be purified by recrystallisation, using water as the solvent. Describe how
you would carry out this recrystallisation, explaining the reason for each step in your method.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................

...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(5)

(ii)

How would you check that the purification had been successful?
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(1)

(c)

(i)

Write the equation for the reaction which occurs when solid benzoic acid is added to sodium
carbonate solution. Include state symbols in your equation.

(2)

(ii)

Benzoic acid is slightly soluble in water. Write the equation for the dissociation of benzoic acid
and hence the expression for the acid dissociation constant, Ka.

(2)

(iii)

Calculate the pH of a 0.00100 mol dm3 solution of benzoic acid.

[Ka for benzoic acid is 6.30 105 mol dm3.]

(3)

(d)

Give the name or formula of an organic compound which, when mixed with a solution of benzoic
acid, forms a buffer solution.

(1)
(Total 21 marks)

180. This question is about compounds with the molecular formula C4H8O.
(a)

(i)

Draw the displayed formulae of TWO isomers, A and B, which are both aldehydes. Give their
systematic names.

Name ....................................................... .......................................................

(4)

(ii)

Suggest an instrumental method by which these isomers, A and B, could be

distinguished.
Outline how the results would differ.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(b)

Substance C, butanone, is another isomer of C4H8O.

(i)

Name a reagent which results in the same observation when it reacts with all three isomers, A,
B and C.
Reagent .............................................................................................................
...........................................................................................................................

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

(ii)

Name a reagent where the resulting observation for C would be different from that for A and
B.
Reagent .............................................................................................................
...........................................................................................................................
Observation with C ...........................................................................................
...........................................................................................................................
...........................................................................................................................
Observation with A and B ................................................................................
...........................................................................................................................
...........................................................................................................................
(3)

(c)

(i)

Suggest structural formulae for TWO more isomers of C4H8O, D and E, which are cyclic and
react with sodium to give off hydrogen.

E
(2)

(ii)

Both A and B can be oxidised to carboxylic acids. These acids will then react with either of the
isomers D or E in the presence of a strong acid as a catalyst.
What is the name given to the products of this type of reaction?

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

(iii)

For one of the carboxylic acids formed from A or B and one of the isomers D or E, draw a
displayed formula of the product formed when they react together.

(2)
(Total 16 marks)

185. (a)

Propanoic acid, CH3CH2COOH, can be prepared from carbon dioxide and an organic reagent.
Name this organic reagent and state the conditions for the preparation.
Reagent ...................................................................................................................
Conditions ...............................................................................................................
................................................................................................................................
(3)

(b)

Describe what you would see and write the equations for the reactions of propanoic acid with:
(i)

a solution of sodium carbonate

Observation ..................................................................................................
Equation .......................................................................................................
(2)

(ii)

solid phosphorus pentachloride.

Observation ..................................................................................................
Equation .......................................................................................................
(2)

(c)

Propanoic acid can also be prepared from propanal, CH3CH2CHO. State the reagents for this
conversion.
Reagents .................................................................................................................
(2)

(d)

1-aminobutan-2-ol, CH3CH2CH(OH)CH2NH2, is an active ingredient in some deodorant sprays.

It can be prepared from propanal by the following two-step process.
Step 1

CH3CH2CHO
(i)

Step 2
CH3CH2CH(OH)CN

CH3CH2CH(OH)CH2NH2

For Step 1
State the reagents and conditions.
......................................................................................................................
......................................................................................................................
Name the type of reaction.
......................................................................................................................
(3)

(ii)

For Step 2
State the reagents and conditions.
......................................................................................................................
......................................................................................................................
Name the type of reaction.
......................................................................................................................
(3)

(e)

Write the structural formula of the organic product formed when 1-aminobutan-2-ol reacts with:
(i)

ethanoyl chloride, CH3COCl

(2)

(ii)

hydrochloric acid.

(1)

(f)

1-aminobutan-2-ol exists as two isomers with the same structural formula.

Identify the type of isomerism and draw the TWO isomers, showing clearly the
difference between them.
Type of isomerism .................................................................................................

(3)
(Total 21 marks)

187. Consider the following reaction scheme:

(a)

(i)

State the catalyst that is needed for Step 1.

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

(ii)

Suggest a synthetic pathway that would enable you to make ethanoyl chloride from ethanol in
two steps. You should give reagents, conditions and the structure of the intermediate compound.
Experimental details and balanced equations are not required.

(4)

(b)

Give the reagents and conditions needed for:

(i)

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

(ii)

Step 3 ...........................................................................................................
......................................................................................................................
(3)

(c)

The IR spectra for compounds A and B are shown.

Table 1
Bond

Assignment

Wavenumber / cm1

Alkanes
Alkenes, arenes

28502950
30003100

Arenes

14501650

C==O

Aldehydes, ketones, esters, carboxylic acids

16801750

OH

Free
Hydrogen bonded in alcohols or phenols
Hydrogen bonded in carboxylic acids

35803670
32303550
25003300

CH
Benzene ring

(i)

Using suitable data from Table 1, give evidence from the spectra which shows that compound A
has been reduced. You will need to comment on both spectra.
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
(3)

(ii)

Compound B is chiral. The IR spectra of the two optical isomers of B are identical. Suggest
why this is so.
......................................................................................................................
......................................................................................................................
(2)

(d)

Both compounds A and B will react with iodine in sodium hydroxide solution to give a yellow
precipitate of triiodomethane (iodoform).
(i)

B is oxidised to A during the reaction. Suggest the identity of the oxidising agent.
......................................................................................................................
(1)

(ii)

Give the equation for the reaction of A with iodine in sodium hydroxide.
......................................................................................................................
......................................................................................................................
(3)

(iii)

Describe a chemical test to show that triiodomethane contains iodine.

......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
(4)
(Total 23 marks)

190. (a)

Carboxylic acids react reversibly with alcohols, in the presence of a catalyst, to form an ester and
water.
When 24.8 g of ethane-1,2-diol, HOCH2CH2OH, was mixed with 66.0 g of ethanoic acid, CH3COOH,
in the presence of a catalyst, equilibrium was reached after 80.0% of the ethane-1,2-diol had reacted.
The total volume at equilibrium was 90.0 cm3.
HOCH2CH2OH + 2CH3COOH

CH3COOCH2CH2OOCCH3 + 2H2O

Write the expression for the equilibrium constant, Kc, and calculate its value. You should make clear
what units, if any, there are for Kc.

(7)

(b)

Ethane-1,2-diol can be made from ethene in a two-stage process. The overall reaction is:
C2H4 + H2O +

1
O2 HOCH2CH2OH
2

1054 g of ethane-1,2-diol was obtained from 560 g of ethene.

Calculate the percentage yield of the process.
(2)

(c)

Polyesters can be formed from compounds with two functional groups.

(i)

Give the structural formula of a reagent that would react with ethane-1,2-diol to make a
polyester. Draw the structure of the polymer made from this reagent and ethane-1,2-diol.

(3)

(ii)

Explain whether it would be sensible for protective clothing, made from this polymer, to be
used in an environment where acid spills are likely.
......................................................................................................................
......................................................................................................................
(1)

(d)

Explain why the ester methyl methanoate, HCOOCH3, has a much lower boiling temperature than its
isomer ethanoic acid, CH3COOH, and why ethanoic acid has a lower boiling temperature than
propanoic acid, C2H5COOH.
................................................................................................................................
................................................................................................................................
................................................................................................................................
................................................................................................................................
................................................................................................................................
................................................................................................................................
................................................................................................................................
................................................................................................................................
................................................................................................................................
................................................................................................................................
(5)
(Total 18 marks)

193. Maleic acid has the structure shown below.

It is a dioic acid and is one of a pair of geometric isomers.

(a)

What is the systematic name for maleic acid?

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

(b)

Write the equation for the reaction of sodium hydroxide with maleic acid, HO2CCH=CHCO2H, to
form disodium maleate (state symbols are not required).

(2)

(c)

Maleic acid has two acid dissociation constants with the following values
Ka1 = 1.48 102 mol dm3
(i)

Ka2 = 8.51 107 mol dm3

Explain why maleic acid has two different Ka values.

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

(ii)

Complete an equation for the first dissociation of maleic acid.

HO2CCH=CHCO2H
(1)

(iii)

Maleic acid is a weak acid. Calculate the pH of a solution of maleic acid of concentration
0.0100 mol dm3 using the value of Ka1 but not Ka2.

(2)

(iv)

Both carboxylic acid groups in maleic acid do dissociate. Suggest how your answer in (c)(iii)
might be affected if you consider Ka2 in addition to Ka1?
................................................................................................................................
................................................................................................................................
(1)
(Total 10 marks)

200. Consider the esterification of the amino acid alanine, which has the formula CH3CH(NH2)COOH.
CH3CH(NH2)COOH + C2H5OH
(a)

(i)

CH3CH(NH2)COOC2H5 + H2O

Write the expression for Kc.

(1)

(ii)

Using the average bond enthalpies given below, show that enthalpy change, H, for this
reaction would be calculated as zero.
Average bond enthalpies / kJ mol1
CO 358

OH 464

(2)

(iii)

On the basis that H is zero, state what the effect of increasing the temperature will be on:
the value of Kc ............................................................................................................
......................................................................................................................
the rate of attainment of equilibrium ..........................................................................
......................................................................................................................
(2)

(b)

Alanine exists as a zwitterion.

(i)

Suggest the structure of this zwitterion.

(1)

(ii)

Suggest why alanine has a relatively high melting temperature.

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

(iii)

Using equations, show how alanine can react with both acid and alkali.

(2)

(c)

The alanine molecule is chiral.

(i)

What is meant by the term chiral?

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

(ii)

Draw the TWO optical isomers of alanine.

(2)

(iii)

How could the optical isomers of alanine be distinguished from each other?
......................................................................................................................
......................................................................................................................
(1)
(Total 13 marks)

206. Study the reaction scheme below, then answer the questions that follow.

(a)

(i)

Butanal contains a carbonyl group. State a chemical test for a carbonyl group and describe the
result of the test.
Test .........................................................................................................................
Result .....................................................................................................................
(2)

(ii)

An isomer of butanal also possesses a carbonyl group, but cannot be oxidised by acidified
sodium dichromate(VI). Give the structural formula of this isomer and its name.
Structural formula ..................................................................................................
Name ......................................................................................................................
(2)

(iii)

Another isomer of butanal contains a carbonyl group and can be oxidised by acidified sodium
dichromate(VI). Draw the displayed formula of this isomer.

(1)

(b)

Compound X is a colourless liquid that smells of pineapples.

(i)

To what class of compounds does X belong?

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

(ii)

Ethanol, C2H5OH, reacts with butanoic acid to form compound X. Complete the diagram below
to show the structural formula of X and the other product.

(1)

(iii)

Give the name of compound X.

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

(iv)

What type of attacking species is ethanol in this reaction?

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

(c)

Describe what you would expect to see during Reaction 2.

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

(d)

Explain why Reaction 4 is far more vigorous than Reaction 3.

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

......................................................................................................................................
(2)
(Total 12 marks)

212. Alanine, 2-aminopropanoic acid, is the simplest chiral amino acid found in nature and is optically active.
H
H2N

C
CH3

(a)

(i)

O
C
O

Explain the meaning of the term chiral.

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

(ii)

How is optical activity detected experimentally?

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

(iii)

If alanine is made from propanoic acid the product mixture does not show optical activity.
Explain why this is so.
......................................................................................................................
......................................................................................................................
......................................................................................................................
(2)

(b)

Alanine reacts with both acids and bases. Give the structural formulae of the compounds you would
expect if alanine reacts with
hydrochloric acid

sodium hydroxide

(2)

(c)

Alanine has a high melting temperature of 300 C, much higher than would be expected for the
structure given at the start of the question.
Draw the structure that is actually present in the solid, and explain why the melting temperature is so
high.

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

(d)

Polyamides are made from a diacid dichloride and a diamine; they are condensation polymers.
(i)

Explain the term condensation polymer.

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

(ii)

Suggest the structural formula of a diacid dichloride and a diamine that could be reacted to form
a polyamide.

(2)

(iii)

Draw sufficient of the polymer chain that would result from the reaction of the compounds in
(ii) to make the structure of the polymer clear.

(2)

(iv)

Alanine could be converted to CH3CH(NH2)COCl which on its own could polymerise to a

polyamide. Draw the structure of the polymer chain showing three alanine repeating units and
all the bonds in the amide links.

(2)
(Total 16 marks)

239. This question is about propanal, CH3CH2CHO, propanone, CH3COCH3, and propanoic acid, CH3CH2CO2H.
(a)

Explain why all three compounds are soluble in water.

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

(b)

Propanal and propanone contain the carbonyl group.

State a chemical test for the presence of this group. Give the result of a positive test.
Test ...........................................................................................................................
Result ........................................................................................................................
(2)

(c)

Propanal can be distinguished from propanone by its oxidation to propanoic acid.

(i)

Name an oxidising agent you would use.

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

(ii)

State the colour change you would observe during the oxidation.
From ...................................................... to ......................................................
(1)

(iii)

State how propanone can be distinguished from propanal using infra-red spectra.
You are not expected to give actual absorption values, but you should indicate the bonds in
the molecules which would give rise to the distinguishing absorptions.
.........................................................................................................................
.........................................................................................................................
(1)

(d)

A useful test for carboxylic acids is that they will neutralise sodium carbonate solution.
Write a balanced equation, including state symbols, for the neutralisation of sodium carbonate solution
by propanoic acid.

(2)

(e)

Give the names of TWO other inorganic chemicals that could be used to make sodium propanoate
from propanoic acid.
....................................................................................................................................
....................................................................................................................................
(2)
(Total 10 marks)