Topic 15
Carbonyls,
Carboxylic Acids
and Chirality
Topic 15 is the organic chemistry of Unit 4. It covers chirality and optical activity, with optical activity as evidence for reaction mechanisms; aldehydes and ketones, their tests, reduction and nucleophilic addition of HCN; carboxylic acids, acyl chlorides, esters and polyesters; and the analytical techniques used to identify organic compounds: high resolution mass spectrometry, carbon-13 and proton NMR, and chromatography including GC and HPLC.
Revision Notes
14 revision notes, in the order the specification teaches them.
Optical Isomerism and Chirality
Optical isomerism and chirality: chiral centres, asymmetric carbon atoms, enantiomers as non-superimposable mirror images and drawing 3D diagrams.
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Optical Activity and Racemic Mixtures
Optical activity: plane-polarised light, enantiomers, racemic mixtures and optical activity as evidence for reaction mechanisms.
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Aldehydes and Ketones: Structure, Naming and Properties
Aldehydes and ketones: functional groups, nomenclature and formulae, the polar carbonyl group, boiling temperatures and solubility in water.
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Oxidation and Tests for Carbonyl Compounds
Oxidation and tests for aldehydes and ketones: Fehling’s solution, Tollens’ reagent, acidified dichromate(VI), 2,4-DNPH, iodoform test.
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Reduction and Nucleophilic Addition of Carbonyl Compounds
Carbonyl reduction with LiAlH₄ and nucleophilic addition of HCN: equations, the mechanism and the formation of hydroxynitriles.
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Carboxylic Acids: Structure, Properties and Preparation
Carboxylic acids: structure and naming, hydrogen bonding, boiling temperature and solubility, and preparation by oxidation and nitrile hydrolysis.
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Reactions of Carboxylic Acids
Reactions of carboxylic acids: salts, esterification, reduction and the formation of acyl chlorides.
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Acyl Chlorides
Acyl chlorides: structure, reactions with water, alcohols, ammonia and amines.
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Esters, Hydrolysis and Polyesters
Esters: naming, formation, acid and alkaline hydrolysis and condensation polymerisation to polyesters.
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High Resolution Mass Spectrometry
High resolution mass spectrometry: accurate relative molecular masses to four decimal places and identifying molecular formulae.
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Carbon-13 NMR Spectroscopy
¹³C NMR spectroscopy: carbon environments, number of peaks, chemical shift and deducing structures.
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Proton NMR Spectroscopy
¹H NMR spectroscopy: chemical shift, integration, the n + 1 rule and splitting patterns, and deducing structures from spectra.
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Chromatography: Paper, Thin-Layer and Rf Values
Chromatography: stationary and mobile phases, paper and thin-layer chromatography and Rf values.
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Gas Chromatography, HPLC and Mass Spectrometry
GC and HPLC: retention times and GC-MS.
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Download, print and revise the reactions of this topic at a glance.
Summary maps
Download, print and revise the reactions of this topic at a glance.
Aldehydes and Ketones Map
Edexcel International A Level Chemistry · Unit 4 · Topic 15
Every reaction on one A4 page: reagents, conditions and reaction type for each arrow, colour coded, with the key tests.
Carboxylic Acids Map
Edexcel International A Level Chemistry · Unit 4 · Topic 15
Every reaction on one A4 page: reagents, conditions and reaction type for each arrow, colour coded, with the key tests.
Acyl Chlorides Map
Edexcel International A Level Chemistry · Unit 4 · Topic 15
Every reaction on one A4 page: reagents, conditions and reaction type for each arrow, colour coded, with the key tests.
Esters Map
Edexcel International A Level Chemistry · Unit 4 · Topic 15
Every reaction on one A4 page: reagents, conditions and reaction type for each arrow, colour coded, with the key tests.
Chirality Map
Edexcel International A Level Chemistry · Unit 4 · Topic 15A Chirality
The whole section on one A4 page: chiral centres, enantiomers, drawing in 3D, optical activity, racemic mixtures and the evidence for mechanisms.
Carbonyl Compounds Summary Map
Edexcel International A Level Chemistry · Unit 4 · Topic 15B Carbonyl Compounds
The whole section on one A4 page: naming, forces and solubility, oxidation tests, reduction, adding HCN, 2,4-DNPH and iodoform.
Carboxylic Acids and Derivatives Summary Map
Edexcel International A Level Chemistry · Unit 4 · Topic 15C Carboxylic Acids and Derivatives
The whole section on one A4 page: carboxylic acids, making them, their reactions, acyl chlorides, esters and polyesters.
Spectroscopy and Chromatography Map
Edexcel International A Level Chemistry · Unit 4 · Topic 15D Spectroscopy and Chromatography
The whole section on one A4 page: high resolution mass spectrometry, ¹³C and ¹H NMR, splitting, paper and thin-layer chromatography, GC and HPLC.
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Specification
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15.1
- 15.1
know that optical isomerism is a result of chirality in molecules with a single chiral centre
Revise
15.2
15.3
- 15.3
know that optical activity is the ability of a single optical isomer to rotate the plane of polarisation of plane-polarised monochromatic light in molecules containing a single chiral centre
Revise
15.4
15.5
15.6
15.7
15.8
- i
understand the reactions of carbonyl compounds with: Fehling’s or Benedict’s solution, Tollens’ reagent and acidified dichromate(VI) ions In equations, the oxidising agent can be represented as [O].
Revise - ii
understand the reactions of carbonyl compounds with: lithium tetrahydridoaluminate(III) (lithium aluminium hydride) in dry ether (ethoxyethane) In equations, the reducing agent can be represented by [H].
Revise - iii
understand the reactions of carbonyl compounds with: HCN, in the presence of KCN, as a nucleophilic addition reaction, using curly arrows, relevant lone pairs, dipoles and evidence of optical activity to show the mechanism
Revise - iv
understand the reactions of carbonyl compounds with: 2,4-dinitrophenylhydrazine (2,4-DNPH), as a qualitative test for the presence of a carbonyl group and to identify a carbonyl compound given data of the melting temperatures of derivatives The equation for this reaction is not required.
Revise - v
understand the reactions of carbonyl compounds with: iodine in the presence of alkali (the iodoform test)
Revise
15.9
15.10
15.11
15.12
- i
understand the reactions of carboxylic acids with: lithium tetrahydridoaluminate(III) (lithium aluminium hydride) in dry ether (ethoxyethane)
Revise - iii
understand the reactions of carboxylic acids with: phosphorus(V) chloride (phosphorus pentachloride)
Revise - iv
understand the reactions of carboxylic acids with: alcohols in the presence of an acid catalyst
Revise
15.13
15.14
15.15
15.16
- 15.16
understand how polyesters such as terylene are formed by condensation polymerisation reactions
Revise
15.17
- i
be able to use data from mass spectra to: suggest possible structures of a simple organic compound given accurate relative molecular masses
Revise - ii
be able to use data from mass spectra to: calculate the accurate relative molecular mass of a compound, given accurate relative atomic masses to four decimal places
Revise
15.18
- 15.18
understand that carbon-13, (13C) NMR spectroscopy provides information about the positions of 13C atoms in a molecule
Revise
15.19
- i
be able to use data from 13C NMR spectroscopy to: predict the different environments for carbon atoms present in a molecule, given values of chemical shift, δ
Revise - ii
be able to use data from 13C NMR spectroscopy to: justify the number of peaks present in a 13C NMR spectrum in terms of the number of carbon atoms in different environments
Revise
15.20
- i
be able to use both low and high resolution proton NMR spectroscopy to: predict the different types of proton present in a molecule, given values of chemical shift, δ
Revise - ii
be able to use both low and high resolution proton NMR spectroscopy to: relate relative peak areas, or ratio number of protons, to the relative numbers of 1H atoms in different environments
Revise - iii
be able to use both low and high resolution proton NMR spectroscopy to: deduce the splitting patterns of adjacent, non-equivalent protons using the (n+1) rule and hence suggest the possible structures for a molecule
Revise - iv
be able to use both low and high resolution proton NMR spectroscopy to: predict the chemical shifts and splitting patterns of the 1H atoms in a given molecule
Revise
15.21
15.22
15.23
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