Edexcel International A Level Chemistry
Topic 10
Alcohols, Halogenoalkanes
& Spectra
Topic 10 is the organic chemistry of Unit 2. Part 10A Alcohols covers naming and classification, oxidation with acidified dichromate(VI), the substitution and elimination reactions of alcohols, and the practical techniques for preparing and purifying a liquid. Part 10B Halogenoalkanes builds the language of mechanisms, then nucleophilic substitution, elimination and the rates of hydrolysis. Part 10C Spectra reads mass spectra and infrared spectra and combines them with chemical tests to identify unknowns. Core Practicals 5, 6, 7 and 8 belong to this topic.
Exam Unit
Unit 2
WCH12/01 – IAS
Specification Points
10.1 – 10.23
23 points covered
Topic Parts
3 parts
12 revision pages
Exam Board
Edexcel IAL
Pearson International
Revision Notes
10.15 – 10.20
Alcohols
naming, oxidation, reactions
1
Available
Topic 10A Alcohols
Naming and classifying alcohols, their hydrogen bonding, oxidation with acidified dichromate(VI), substitution and elimination reactions, and the techniques for preparing and purifying a liquid product (Core Practical 7).
Start revising10.1 – 10.14
Halogenoalkanes
nucleophiles, substitution, elimination
2
Available
Topic 10B Halogenoalkanes
Reaction types and mechanisms, naming and classifying halogenoalkanes, nucleophilic substitution with hydroxide, water, ammonia and cyanide, elimination with ethanolic KOH, and rates of hydrolysis (Core Practicals 5 and 6).
Start revising10.21 – 10.23
Spectra
mass spectra, infrared, unknowns
3
Available
Topic 10C Spectra
Molecular ions and fragmentation in mass spectra, infrared absorptions of functional groups, and combining spectra with chemical tests to identify unknown compounds (Core Practical 8).
Start revisingSpecification Coverage
Topic 10 Alcohols, Halogenoalkanes and Spectra – Edexcel International A Level Chemistry
The following specification points outline the knowledge and skills students are expected to demonstrate for Topic 10.
10A: Alcohols (10.15 – 10.20)
10.15
understand the nomenclature of alcohols and be able to draw their structural, displayed and skeletal formulae
10.16
understand the distinction between primary, secondary and tertiary alcohols
10.17
understand the reactions of alcohols with:
i
oxygen in air (combustion)
ii
PCl₅ to produce chloroalkanes (also a qualitative test for the –OH group), 50% concentrated sulfuric acid and potassium bromide to produce bromoalkanes, and red phosphorus and iodine to produce iodoalkanes
iii
concentrated phosphoric acid to form alkenes by elimination (mechanisms not required)
10.18
understand that potassium dichromate(VI) in dilute sulfuric acid can oxidise:
i
primary alcohols to aldehydes (positive Benedict’s or Fehling’s test) if the product is distilled as it forms
ii
primary alcohols to carboxylic acids (positive test with sodium carbonate or sodium hydrogencarbonate) if heated under reflux
iii
secondary alcohols to ketones; the oxidising agent can be represented by [O]
10.19
understand the following techniques in the preparation and purification of a liquid organic compound:
i
heating under reflux
ii
extraction with a solvent using a separating funnel
iii
distillation
iv
drying with an anhydrous salt
v
boiling temperature determination
10.20
CORE PRACTICAL 7: the oxidation of propan-1-ol to produce propanal and propanoic acid
10B: Halogenoalkanes (10.1 – 10.14)
10.1
be able to classify reactions as addition, elimination, substitution, oxidation, reduction, hydrolysis or polymerisation
10.2
understand the concept of a reaction mechanism
10.3
understand that heterolytic bond breaking results in electrophiles and nucleophiles
10.4
know the definition of the term nucleophile
10.5
understand the link between bond polarity and the type of reaction mechanism a compound will undergo
10.6
understand the nomenclature of halogenoalkanes and be able to draw their structural, displayed and skeletal formulae
10.7
understand the distinction between primary, secondary and tertiary halogenoalkanes
10.8
understand the reactions of halogenoalkanes with:
i
aqueous alkali, including KOH(aq), to produce alcohols (hydroxide ion as a nucleophile)
ii
ethanolic potassium hydroxide to produce alkenes by elimination (hydroxide ion as a base)
iii
aqueous silver nitrate in ethanol (water as a nucleophile)
iv
alcoholic ammonia under pressure to produce amines (ammonia as a nucleophile)
v
alcoholic potassium cyanide to produce nitriles (cyanide ion as a nucleophile), an example of increasing the length of the carbon chain
10.9
understand the mechanisms of the nucleophilic substitution reactions between primary halogenoalkanes and aqueous potassium hydroxide, and ammonia (Sₙ1 and Sₙ2 mechanisms are tested in Unit 4)
10.10
understand that experimental observations and data can be used to compare the relative rates of hydrolysis of:
i
primary, secondary and tertiary structural isomers of a halogenoalkane
ii
primary chloro-, bromo- and iodoalkanes using aqueous silver nitrate in ethanol
10.11
CORE PRACTICAL 5: investigation of the rates of hydrolysis of some halogenoalkanes
10.12
know the trend in reactivity of primary, secondary and tertiary halogenoalkanes
10.13
understand the trend in reactivity of chloro-, bromo- and iodoalkanes in terms of bond enthalpy
10.14
CORE PRACTICAL 6: chlorination of 2-methylpropan-2-ol with concentrated hydrochloric acid
10C: Spectra (10.21 – 10.23)
10.21
be able to interpret data from mass spectra to suggest possible structures of simple organic compounds using the m/z of the molecular ion and fragmentation patterns
10.22
be able to use infrared spectra, or data from them, to deduce functional groups present and to predict absorptions, given wavenumber data, for:
i
C–H stretching in alkanes, alkenes and aldehydes
ii
C=C stretching in alkenes
iii
O–H stretching in alcohols and carboxylic acids
iv
C=O stretching in aldehydes, ketones and carboxylic acids
v
C–X stretching in halogenoalkanes
vi
N–H stretching in amines
10.23
CORE PRACTICAL 8: analysis of some inorganic and organic unknowns
Specification Coverage
Topic 10 Alcohols, Halogenoalkanes and Spectra – Edexcel International A Level Chemistry
The following specification points outline the knowledge and skills students are expected to demonstrate for Topic 10.
10A: Alcohols (10.15 – 10.20)
10.15
understand the nomenclature of alcohols and be able to draw their structural, displayed and skeletal formulae
10.16
understand the distinction between primary, secondary and tertiary alcohols
10.17
understand the reactions of alcohols with:
i
oxygen in air (combustion)
ii
PCl₅ to produce chloroalkanes (also a qualitative test for the –OH group), 50% concentrated sulfuric acid and potassium bromide to produce bromoalkanes, and red phosphorus and iodine to produce iodoalkanes
iii
concentrated phosphoric acid to form alkenes by elimination (mechanisms not required)
10.18
understand that potassium dichromate(VI) in dilute sulfuric acid can oxidise:
i
primary alcohols to aldehydes (positive Benedict’s or Fehling’s test) if the product is distilled as it forms
ii
primary alcohols to carboxylic acids (positive test with sodium carbonate or sodium hydrogencarbonate) if heated under reflux
iii
secondary alcohols to ketones; the oxidising agent can be represented by [O]
10.19
understand the following techniques in the preparation and purification of a liquid organic compound:
i
heating under reflux
ii
extraction with a solvent using a separating funnel
iii
distillation
iv
drying with an anhydrous salt
v
boiling temperature determination
10.20
CORE PRACTICAL 7: the oxidation of propan-1-ol to produce propanal and propanoic acid
10B: Halogenoalkanes (10.1 – 10.14)
10.1
be able to classify reactions as addition, elimination, substitution, oxidation, reduction, hydrolysis or polymerisation
10.2
understand the concept of a reaction mechanism
10.3
understand that heterolytic bond breaking results in electrophiles and nucleophiles
10.4
know the definition of the term nucleophile
10.5
understand the link between bond polarity and the type of reaction mechanism a compound will undergo
10.6
understand the nomenclature of halogenoalkanes and be able to draw their structural, displayed and skeletal formulae
10.7
understand the distinction between primary, secondary and tertiary halogenoalkanes
10.8
understand the reactions of halogenoalkanes with:
i
aqueous alkali, including KOH(aq), to produce alcohols (hydroxide ion as a nucleophile)
ii
ethanolic potassium hydroxide to produce alkenes by elimination (hydroxide ion as a base)
iii
aqueous silver nitrate in ethanol (water as a nucleophile)
iv
alcoholic ammonia under pressure to produce amines (ammonia as a nucleophile)
v
alcoholic potassium cyanide to produce nitriles (cyanide ion as a nucleophile), an example of increasing the length of the carbon chain
10.9
understand the mechanisms of the nucleophilic substitution reactions between primary halogenoalkanes and aqueous potassium hydroxide, and ammonia (Sₙ1 and Sₙ2 mechanisms are tested in Unit 4)
10.10
understand that experimental observations and data can be used to compare the relative rates of hydrolysis of:
i
primary, secondary and tertiary structural isomers of a halogenoalkane
ii
primary chloro-, bromo- and iodoalkanes using aqueous silver nitrate in ethanol
10.11
CORE PRACTICAL 5: investigation of the rates of hydrolysis of some halogenoalkanes
10.12
know the trend in reactivity of primary, secondary and tertiary halogenoalkanes
10.13
understand the trend in reactivity of chloro-, bromo- and iodoalkanes in terms of bond enthalpy
10.14
CORE PRACTICAL 6: chlorination of 2-methylpropan-2-ol with concentrated hydrochloric acid
10C: Spectra (10.21 – 10.23)
10.21
be able to interpret data from mass spectra to suggest possible structures of simple organic compounds using the m/z of the molecular ion and fragmentation patterns
10.22
be able to use infrared spectra, or data from them, to deduce functional groups present and to predict absorptions, given wavenumber data, for:
i
C–H stretching in alkanes, alkenes and aldehydes
ii
C=C stretching in alkenes
iii
O–H stretching in alcohols and carboxylic acids
iv
C=O stretching in aldehydes, ketones and carboxylic acids
v
C–X stretching in halogenoalkanes
vi
N–H stretching in amines
10.23
CORE PRACTICAL 8: analysis of some inorganic and organic unknowns
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