Chemistry Unit 4 All 6 Marks Questions

- Compiled by Raiyad Reza

Jan 2020

Compare and contrast the reactions of propanal and propanone with one oxidising agent,
one reducing agent and 2,4-dinitrophenylhydrazine.
In your answer include any relevant observations for the reactions you discuss and
equations for any reactions classified as oxidation, using [O] for the oxygen from the
oxidising agent.

Similarities

• Both react with 2,4-dinitrophenylhydrazine to form a yellow / orange / red precipitate

• Both can be reduced by LiAlH4 / Lithium tetrahydrido aluminate / lithium aluminium hydride
(in dry ether)

Differences:

• but propanal forms a primary alcohol, propanone forms a secondary alcohol

• Propanal will react with acidified potassium dichromate ((VI)) but propanone will not react

• Equation for oxidation reaction

CH3CH2CHO + [O] → CH3CH2COOH

• Observation for named oxidising agent

Eg. orange to green (with acidified dichromate(VI)
October 2020

Explain one advantage and one disadvantage of using a temperature higher than 700 K in
the Haber process.
Consider the effect of an increase in temperature on the rate of reaction, on the
values of ∆S surroundings and ∆S total and on the equilibrium constant.

• Rate of reaction is higher / faster

• More ammonia produced in a given time

• At higher temperature ΔSsurr is less positive / decreases / smaller

• ΔStotal more negative / less positive

• Kp decreases

• equilibrium position moves further left / in the endothermic direction / in reverse direction /
gives lower yield of ammonia / makes reaction less feasible
Jan 2021

Explain, in terms of all the intermolecular forces involved, why butanal has a
higher boiling temperature than pentane but a lower boiling temperature than
propanoic acid.

• Pentane (only) has London forces / all have London forces

• Butanal (also) has (permanent) dipole-dipole interactions

• Propanoic acid (also) has (dipole-dipole and) hydrogen bonding

• The London forces have about the same strength as they have a similar number of electrons /
pentane has 42, butanal has 40 (and propanoic acid has 40 electrons)

• Dipole-dipole interactions are stronger than London forces

• Hydrogen bonding is stronger than dipole-dipole interactions

June 2021 (Unseen Paper)

The table shows the theoretical and experimental (Born-Haber) lattice energy data for
two metal halide compounds, sodium chloride and magnesium iodide.

Using the data, compare and contrast the type and strength of bonding
in these compounds.
Give reasons for your answers.

• Bonding in sodium chloride is (almost) 100% ionic bonds and as the theoretical and Born-
Haber values are (very) similar

• Bonding in magnesium iodide has some covalent character and as theoretical and Born-
Haber values are (significantly) different

• Anion is (more) polarised in magnesium iodide (than sodium chloride)

• Magnesium ion has a greater charge density (than sodium ion), so greater polarising power

• Iodide ion is larger (than chloride ion), so is more easily polarised

• Magnesium iodide has stronger bonding than sodium chloride because the charge on the
magnesium ion is twice as large (as the charge on the sodium ion)
October 2021

The hydrolysis of halogenoalkanes by alkali is a nucleophilic substitution reaction.

RX + OH− → ROH + X−

The mechanism of this reaction for primary halogenoalkanes is different from the
mechanism for tertiary halogenoalkanes.

Describe how knowledge of the rate equations for the hydrolysis of halogenoalkanes
provides evidence for the mechanisms of these reactions.
Curly arrow mechanisms are not required.

• the rate equation for primary halogenoalkanes

• the rate equation for tertiary halogenoalkanes

• primary halogenoalkanes react by SN2

• and tertiary halogenoalkanes react by SN1

• for primary halogenoalkanes the slow step / RDS is when the compound reacts with
hydroxide ions via a transition state

• for tertiary halogenoalkanes the slow step / RDS is when the compound forms a carbocation
(in a step that only involves the halogenoalkane)
Jan 2022

Compound A is thought to be another isomer of hexanoic acid.

A series of tests was performed on compound A.

Deduce the structure for compound A.

Justify your answer by using all the test results.

• Misty fumes suggest OH group present

• Orange precipitate suggests a carbonyl group is present (so no carboxylic acid, must be
alcohol)

• (Negative) Benedict’s / Fehling’s reagent suggests no aldehyde group present / a ketone is

present

• Acidified potassium dichromate(VI) suggests not a primary, a secondary alcohol or an

aldehyde present

• Polarimetry indicates a chiral centre is present / it is a chiral molecule

• Structure of 3-hydroxy-3-methylpentan-2-one
June 2022

Compare and contrast the reactions of ethanoyl chloride with water, with ethanol
and with ammonia.
Refer to the structural features of the molecules that determine the type of reaction.
Identify the products of the reactions. You may include equations in your answers.

Similarities

• the Cl is lost in all reactions

• water, ethanol and ammonia all contain a lone pair that attacks the delta+ carbon atom in
ethanoyl chloride

• all reactions are very vigorous/violent

Differences

• water: forms ethanoic acid/ CH3COOH

(CH3COCl + H2O) → CH3COOH (+ HCl)

• ethanol: forms ethyl ethanoate/ CH3COOCH2CH3

(CH3COCl + CH3CH2OH) → CH3COOCH2CH3 (+ HCl)

• Ammonia: forms ethanamide/ CH3CONH2

(CH3COCl + 2NH3) → CH3CONH2 (+ NH4Cl)
October 2022

Sodium ethanoate, CH3COONa , reacts with 2-methylpropanoyl chloride,

(CH3)2CHCOCl, to form organic compound Z and sodium chloride, NaCl.

The molecular ion peak in the mass spectrum of Z is at m / z = 130.

The infrared spectrum of Z has peaks at 1820 cm−1 and 1754 cm−1 .
The carbon-13 NMR spectrum of Z has five peaks.
A simplified high resolution proton NMR spectrum of Z is shown.
The number of protons in each environment is indicated on the spectrum

Deduce the structure of Z, showing how your answer is consistent with all the
information provided.

• confirmation of RMM/molar mass/molecular formula (from molecular ion peak)

• interpretation of IR data

• interpretation of carbon-13 NMR data

• identification of fragment causing singlet proton NMR peak

• identification of fragment causing doublet NMR peak and septet NMR peak

• structure of Z
Jan 2023

Lactic acid is formed in muscles and in sour milk.

Lactic acid may be obtained from ethanal in the laboratory by the two-step
synthesis shown.

Explain why lactic acid formed in muscles is optically active while lactic acid
obtained using the laboratory synthesis is not.
You should define any terms you use.

• ‘optically active’ means that these molecules rotate the plane of plane-polarised light

• lactic acid (is optically active because its) molecules can form non-superimposable mirror
images

• lactic acid formed in muscles contains one type of enantiomer and lactic acid formed in the
synthesis contains equal numbers of moles of the two enantiomers

• the carbonyl group is planar

• (in the synthesis the) nucleophile / CN− attacks (equally) from above and below the plane (of
the carbonyl group)

• (because) lactic acid formed in muscles involves the oxidation of an enantiomer in a way that
does not involve the chiral centre
May 2023

The high resolution proton NMR spectrum of one of these isomers is shown.

Deduce which isomer is present in the sample, explaining the splitting

patterns and chemical shifts seen in the spectrum.
Include the name of the isomer and the relative peak areas.
Use your Data Booklet.

• 3 peaks so 3 (proton/hydrogen/H) environments

• the peak in the range 3.7‒ 4.2 (δ/ppm) is the H attached to the same carbon as the bromine

• split into 5 peaks as next to 4 hydrogens

• the peak at 0.8 ‒ 1.3 (δ/ppm) is the Hs in the methyl groups and the peak at 1.6 ‒ 2.2
(δ/ppm) is the two -CH2- hydrogen groups

• peak areas [Link]

• identification of 3-bromopentane by name or structural formula

October 2023

This question is about four isomers with the molecular formula C4H8O2.

These four isomers can be identified using three chemical tests.

Each test gives a positive result for only one isomer.
All three tests give a negative result for the fourth isomer.
Deduce the three chemical tests required. For each test
• identify the reagent
• give the positive observation in each test
• identify the functional group of the isomer that gives the positive result.

• sodium carbonate solution / sodium hydrogencarbonate solution gives fizzing (due to the
formation of carbon dioxide)

• identifies butanoic acid is the only (carboxylic) acid / compound with an acidic proton / only
compound with – COOH

• Tollens’ reagent / ammoniacal silver nitrate gives a silver mirror

• identifies 4-hydroxybutanal, which is the only aldehyde / only compound containing –CHO

• iodine and sodium hydroxide (solution) gives a yellow precipitate / antiseptic smell

• identifies 3-hydroxybutanone, which is the only compound with a CH3CO‒ group / only
compound with a methyl ketone group
Jan 2024

Lattice energies from the Born–Haber cycle are based on experimental values.
Theoretical lattice energies can also be calculated. Experimental and theoretical
values for three different crystal lattices are shown.

Discuss the reasons for the differences in these six values of lattice energy in
terms of the structure and bonding in these three substances.

• The magnesium (ion) has larger charge/smaller ionic radius than the sodium (ion)

• The attraction between the ions/ionic bond is stronger in magnesium fluoride (so lattice
energies of sodium fluoride are less exothermic)

• The magnesium ion is more polarising than the sodium ion

• The chloride ion is larger/ more polarisable than the fluoride ion

• The difference between theoretical and experimental values is greatest for magnesium
chloride / the difference between theoretical and experimental values is least for sodium
fluoride

• Magnesium chloride has the greatest degree of covalent character/Sodium fluoride has the
greatest degree of ionic character