Carboxylic Acids and Derivatives QP

AQA Chemistry A-Level - Carboxylic Acids + Derivatives QP PhysicsAndMathsTutor.
com
Q1.
Which statement about (CH3)2CHCH2COOH is correct?
A In aqueous solution it reacts with magnesium to form

carbon dioxide.
B It can form hydrogen bonds.
C It has optical isomers.
D It has the IUPAC name 2-methylbutanoic acid.

(Total 1 mark)
Q2.
Which compound is formed when phenyl benzenecarboxylate is hydrolysed
under acidic conditions?
A C6H5CH2OH
B C6H5CHO
C C6H5COCH3
D C6H5COOH
(Total 1 mark)
Q3.
This question is about esters including biodiesel.
(a) An ester is formed by the reaction of an acid anhydride with CH3CH2OH
Complete the equation. In your answer show clearly the structure of the
ester.
Give the IUPAC name of the ester.
Equation
Name of ester
_______________________________________________________
(3)
Page 1 of 14
AQA Chemistry A-Level - Carboxylic Acids + Derivatives QP PhysicsAndMathsTutor.com
(b) In a reaction to form biodiesel, one mole of a vegetable oil reacts with an
excess of methanol to form two moles of an ester with molecular formula
C19H34O2 and one mole of an ester with molecular formula C19H36O2
Draw the structure of the vegetable oil showing clearly the ester links.
You should represent the hydrocarbon chains in the form CxHy where x and
y are the actual numbers of carbon and hydrogen atoms.
(2)
(c) The compound C19H34O2 is the methyl ester of Z,Z-octadeca-9,12-dienoic

acid.
Part of the structure of the acid is shown.
Complete the skeletal formula to show the next part of the hydrocarbon
chain to carbon atom number 14.
In your answer, show the Z stereochemistry around both C=C double
bonds.
(2)
(d) Give an equation for the complete combustion of the ester C19H34O2
___________________________________________________________
(1)
Page 2 of 14
(e) Combustion of biodiesel produces greenhouse gases such as carbon

dioxide that cause global warming.
Part of the infrared spectrum of carbon dioxide is shown in the diagram.
State how the infrared spectrum of carbon dioxide in the diagram above is
not what you might predict from the data provided in Table A in the Data
Booklet.
___________________________________________________________
___________________________________________________________
___________________________________________________________
(1)
(f) Explain how carbon dioxide causes global warming.
___________________________________________________________
___________________________________________________________
___________________________________________________________
___________________________________________________________
___________________________________________________________
___________________________________________________________
(2)
(Total 11 marks)
Page 3 of 14
Q4.
Which compound is formed by acid hydrolysis of phenylmethyl ethanoate?
A C6H5CH2OH
B C6H5CHO
C C6H5COCH3
D C6H5COOH
(Total 1 mark)
Q5.
Acyl chlorides are useful reagents in synthesis. They react with aromatic
compounds and also with alcohols.
(a) CH3CH2COCl reacts with benzene in the presence of AlCl3 in an

electrophilic substitution reaction.
Give an equation for the reaction of CH3CH2COCl with AlCl3 to form the
electrophile.
Outline a mechanism for the reaction of this electrophile with benzene.
Equation
___________________________________________________________
Mechanism
(4)
Page 4 of 14
(b) The organic product in part (a) can be converted into the alcohol shown.
Give the IUPAC name of the alcohol.

Give the reagent needed for this reaction and name the mechanism.
IUPAC name
_______________________________________________________
Reagent
___________________________________________________________
Name of mechanism
_________________________________________________
(3)
(c) The alcohol shown in part (b) reacts with ethanoyl chloride to form an
ester.
Describe what would be observed when the alcohol reacts with ethanoyl
chloride.
Name the mechanism for the reaction to form the ester.
Draw the structure of the ester.
Observation
________________________________________________________
___________________________________________________________
Name of mechanism
__________________________________________________
Structure of ester
(3)
(Total 10 marks)
Page 5 of 14
Q6.
A four-step synthesis of compound T is shown.
(a) Give the reagent and conditions for Step 1.

State how you could obtain a sample of the alcohol from the reaction
mixture formed in Step 1.
___________________________________________________________
___________________________________________________________
___________________________________________________________
___________________________________________________________
___________________________________________________________
(3)
(b) Draw the structure of compound S.

For each of Steps 3 and 4, give a reagent and one condition, other than
heat.
(5)
(Total 8 marks)
Page 6 of 14
Q7.
Coconut oil contains a triester with three identical R groups.
This triester reacts with potassium hydroxide.
(a) Complete the equation by drawing the structure of the other product of this
reaction in the box.
Name the type of compound shown by the formula RCOOK
Give one use for this type of compound.
Type of compound ___________________________________________
Use _______________________________________________________
(3)
(b) The triester in coconut oil has a relative molecular mass, Mr = 638.0
In the equation shown at the start of this question, R represents an alkyl
group that can be written as CH3(CH2)n
Deduce the value of n in CH3(CH2)n

Show your working.
n _______________
(3)
Page 7 of 14
(c) A 1.450 g sample of coconut oil is heated with 0.421 g of KOH in aqueous
ethanol until all of the triester is hydrolysed.
The mixture is cooled.
The remaining KOH is neutralised by exactly 15.65 cm3 of 0.100 mol dm–3
HCl
Calculate the percentage by mass of the triester (Mr = 638.0) in the

coconut oil.
Percentage by mass _______________

(6)
(d) Suggest why aqueous ethanol is a suitable solvent when heating the
coconut oil with KOH.
Give a safety precaution used when heating the mixture.

Justify your choice.
Reason ____________________________________________________
___________________________________________________________
Safety
precaution __________________________________________________
___________________________________________________________
Justification _________________________________________________
___________________________________________________________
(3)
Page 8 of 14
(Total 15 marks)
Q8.
This question is about making a diester from cyclohexanol.
(a) State the type of reaction in step 1.
Give the name of the reagent needed for step 1.
Type of reaction ______________________________________________
Reagent ____________________________________________________
(2)
(b) State the reagents needed and give equations for step 2 and step 3.
Show the structure of Compound G in your equations.
Step 2 reagent _______________________________________________
Step 2 equation
___________________________________________________________
Step 3 reagent _______________________________________________
Step 3 equation
___________________________________________________________
(4)
(c) Cyclohexane-1,2-diol reacts with ethanedioyl dichloride.
Give the name of the mechanism for this reaction.
Complete the mechanism to show the formation of one ester link in the first
step of this reaction.
Mechanism name _____________________________________________
Page 9 of 14
Mechanism
(5)
(d) Suggest why chemists usually aim to design production methods

• with fewer steps
• with a high percentage atom economy.
Fewer steps ________________________________________________
___________________________________________________________
___________________________________________________________
High percentage atom economy _________________________________
___________________________________________________________
___________________________________________________________
(2)
(Total 13 marks)
Q9.
Aspirin can be produced by reacting salicylic acid with ethanoic anhydride.
An incomplete method to determine the yield of aspirin is shown.
1. Add about 6 g of salicylic acid to a weighing boat.

2. Place the weighing boat on a 2 decimal place balance and record the
mass.
3. Tip the salicylic acid into a 100 cm3 conical flask.
4. ______________________________________________
5. Add 10 cm3 of ethanoic anhydride to the conical flask and swirl.
6. Add 5 drops of concentrated phosphoric acid.
7. Warm the flask for 20 minutes.
8. Add ice-cold water to the reaction mixture and place the flask in an ice
bath.
9. Filter off the crude aspirin from the mixture and leave it to dry.
10. Weigh the crude aspirin and calculate the yield.
Page 10 of 14
(a) Describe the instruction that is missing from step 4 of the method.
Justify why this step is necessary.
Instruction
___________________________________________________________
Justification
___________________________________________________________
___________________________________________________________
___________________________________________________________
(2)
(b) Suggest a suitable piece of apparatus to measure out the ethanoic

anhydride in step 5.
___________________________________________________________
(1)
(c) Identify a hazard of using concentrated phosphoric acid in step 6.
___________________________________________________________
(1)
(d) Complete the equation for the reaction of salicylic acid with ethanoic
anhydride to produce aspirin.
(1)
Page 11 of 14
(e) A 6.01 g sample of salicylic acid (Mr = 138.0) is reacted with

10.5 cm3 of ethanoic anhydride (Mr = 102.0).
In the reaction the yield of aspirin is 84.1%
The density of ethanoic anhydride is 1.08 g cm–3
Show by calculation which reagent is in excess.
Calculate the mass, in g, of aspirin (Mr = 180.0) produced.
Reagent in excess _______________
Mass of aspirin __________ g

(5)
(f) Suggest two ways in which the melting point of the crude aspirin collected
in step 9 would differ from the melting point of pure aspirin.
Difference 1
___________________________________________________________
___________________________________________________________
Difference 2
___________________________________________________________
___________________________________________________________
(2)
Page 12 of 14
(g) The crude aspirin can be purified by recrystallisation using hot ethanol
(boiling point = 78 °C) as the solvent.
Describe two important precautions when heating the mixture of ethanol

and crude aspirin.
Precaution 1
________________________________________________________
___________________________________________________________
Precaution 2
________________________________________________________
___________________________________________________________
(2)
(h) The pure aspirin is filtered under reduced pressure.

A small amount of cold ethanol is then poured through the Buchner funnel.
Explain the purpose of adding a small amount of cold ethanol.
___________________________________________________________
___________________________________________________________
___________________________________________________________
(1)
(i) A sample of the crude aspirin is kept to compare with the purified aspirin.
Describe one difference in appearance you would expect to see between

these two solid samples.
___________________________________________________________
___________________________________________________________
___________________________________________________________
(1)
(Total 16 marks)
Page 13 of 14
Q10.
Which reaction involves addition-elimination?
A (CH3)2CHBr + KOH → CH3CH=CH2 + KBr + H2O
B CH3COCl + C6H5OH → CH3COOC6H5 + HCl
C CH3CH=CH2 + Cl2 → CH3CHClCH2Cl
D CH3CH2CH2Br + NaOH → CH3CH2CH2OH +

NaBr
(Total 1 mark)
Page 14 of 14

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AQA Chemistry A-Level - Carboxylic Acids + Derivatives QP PhysicsAndMathsTutor.

A In aqueous solution it reacts with magnesium to form

B It can form hydrogen bonds.

C It has optical isomers.

D It has the IUPAC name 2-methylbutanoic acid.

(a) An ester is formed by the reaction of an acid anhydride with CH3CH2OH

(c) The compound C19H34O2 is the methyl ester of Z,Z-octadeca-9,12-dienoic

Part of the structure of the acid is shown.

(e) Combustion of biodiesel produces greenhouse gases such as carbon

(f) Explain how carbon dioxide causes global warming.

(a) CH3CH2COCl reacts with benzene in the presence of AlCl3 in an

Give the IUPAC name of the alcohol.

(a) Give the reagent and conditions for Step 1.

(b) Draw the structure of compound S.

Name the type of compound shown by the formula RCOOK

Give one use for this type of compound.

Type of compound ___________________________________________

Deduce the value of n in CH3(CH2)n

Calculate the percentage by mass of the triester (Mr = 638.0) in the

Percentage by mass _______________

Give a safety precaution used when heating the mixture.

(a) State the type of reaction in step 1.

Give the name of the reagent needed for step 1.

Type of reaction ______________________________________________

Show the structure of Compound G in your equations.

Step 2 reagent _______________________________________________

Step 3 reagent _______________________________________________

(c) Cyclohexane-1,2-diol reacts with ethanedioyl dichloride.

Give the name of the mechanism for this reaction.

Mechanism name _____________________________________________

(d) Suggest why chemists usually aim to design production methods

Fewer steps ________________________________________________

High percentage atom economy _________________________________

1. Add about 6 g of salicylic acid to a weighing boat.

Justify why this step is necessary.

(b) Suggest a suitable piece of apparatus to measure out the ethanoic

(c) Identify a hazard of using concentrated phosphoric acid in step 6.

(e) A 6.01 g sample of salicylic acid (Mr = 138.0) is reacted with

The density of ethanoic anhydride is 1.08 g cm–3

Show by calculation which reagent is in excess.

Calculate the mass, in g, of aspirin (Mr = 180.0) produced.

Reagent in excess _______________

Mass of aspirin __________ g

Describe two important precautions when heating the mixture of ethanol

(h) The pure aspirin is filtered under reduced pressure.

Explain the purpose of adding a small amount of cold ethanol.

Describe one difference in appearance you would expect to see between

A (CH3)2CHBr + KOH → CH3CH=CH2 + KBr + H2O

B CH3COCl + C6H5OH → CH3COOC6H5 + HCl

C CH3CH=CH2 + Cl2 → CH3CHClCH2Cl

D CH3CH2CH2Br + NaOH → CH3CH2CH2OH +

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