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Cambridge International AS & A Level Chemistry – Organic Chemistry

Topic 16
Hydroxy Compounds

Topic 16 covers the six routes to alcohols (hydration, diol formation, substitution of halogenoalkanes, reduction of carbonyls and acids, ester hydrolysis), combustion, substitution to halogenoalkanes with HX, KCl and concentrated acid, PCl₃, PCl₅ and SOCl₂, the reaction with sodium, oxidation with acidified dichromate(VI) or manganate(VII) by distillation or reflux, dehydration with a heated catalyst or concentrated acid, esterification, classification, the tri-iodomethane test and the acidity of alcohols compared with water.

Exam Papers
Papers 1 & 2
9701 AS Level
Learning Outcomes
16.1.1 – 16.1.5
5 sections covered
Topic Parts
5 pages
Revision notes available
Exam Board
Cambridge
9701 (2025 onwards)

Revision Notes

Work through Topic 16 Hydroxy Compounds in a structured sequence.

The –OH group
Naming and
Classifying
1
Available

Alcohols: Naming, Classification and Properties

Alcohols: nomenclature, structural, displayed and skeletal formulae, primary, secondary and tertiary alcohols, hydrogen bonding, boiling temperatures and solubility.

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Two routes
Producing
Alcohols
2
Available

Producing Alcohols: Hydration, Fermentation and Biofuels

Producing ethanol: hydration of ethene, fermentation of glucose, conditions and comparison, biofuels and carbon neutrality.

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Orange to green
Oxidation of
Alcohols
3
Available

Oxidation of Alcohols

The oxidation of alcohols: acidified dichromate(VI), aldehydes, carboxylic acids and ketones, distillation versus reflux, [O] equations and tests for aldehydes and acids.

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Reaction map
Reactions of
Alcohols
4
Available

Substitution and Elimination Reactions of Alcohols

Reactions of alcohols: combustion, halogenation with PCl₅, KBr and sulfuric acid, and red phosphorus and iodine, and dehydration to alkenes.

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Practical skills
Preparing and
Purifying
5
Available

Preparing and Purifying Organic Liquids

Preparing and purifying organic liquids: reflux, distillation, separating funnel, drying agents, boiling temperature and percentage yield.

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Specification Coverage

Topic 16 Hydroxy Compounds – Cambridge International AS Level Chemistry

The following Cambridge learning outcomes state what candidates should be able to do. Wording is taken from the Cambridge International AS & A Level Chemistry (9701) syllabus.

16.1 Alcohols

16.1.1(a)
recall the reaction (reagents and conditions) by which alcohols can be produced: electrophilic addition of steam to an alkene, H₂O(g) and H₃PO₄ catalyst
16.1.1(b)
recall the reaction (reagents and conditions) by which alcohols can be produced: reaction of alkenes with cold dilute acidified potassium manganate(VII) to form a diol
16.1.1(c)
recall the reaction (reagents and conditions) by which alcohols can be produced: substitution of a halogenoalkane using NaOH(aq) and heat
16.1.1(d)
recall the reaction (reagents and conditions) by which alcohols can be produced: reduction of an aldehyde or ketone using NaBH₄ or LiAlH₄
16.1.1(e)
recall the reaction (reagents and conditions) by which alcohols can be produced: reduction of a carboxylic acid using LiAlH₄
16.1.1(f)
recall the reaction (reagents and conditions) by which alcohols can be produced: hydrolysis of an ester using dilute acid or dilute alkali and heat
16.1.2(a)
describe the reaction of alcohols with oxygen (combustion)
16.1.2(b)-i
describe substitution of alcohols to form halogenoalkanes by reaction with HX(g)
16.1.2(b)-ii
describe substitution of alcohols to form halogenoalkanes with KCl and concentrated H₂SO₄ or concentrated H₃PO₄
16.1.2(b)-iii
describe substitution of alcohols to form halogenoalkanes with PCl₃ and heat
16.1.2(b)-iv
describe substitution of alcohols to form halogenoalkanes with PCl₅
16.1.2(b)-v
describe substitution of alcohols to form halogenoalkanes with SOCl₂
16.1.2(c)
describe the reaction of alcohols with Na(s)
16.1.2(d)(i)
describe oxidation of alcohols with acidified K₂Cr₂O₇ or acidified KMnO₄ to carbonyl compounds by distillation
16.1.2(d)(ii)-a
describe oxidation of alcohols with acidified K₂Cr₂O₇ or acidified KMnO₄ to carboxylic acids by refluxing
16.1.2(d)(ii)-b
describe that primary alcohols give aldehydes which can be further oxidised to carboxylic acids
16.1.2(d)(ii)-c
describe that secondary alcohols give ketones
16.1.2(d)(ii)-d
describe that tertiary alcohols cannot be oxidised
16.1.2(e)-i
describe dehydration of alcohols to an alkene, by using a heated catalyst, e.g. Al₂O₃
16.1.2(e)-ii
describe dehydration of alcohols to an alkene, by using a concentrated acid
16.1.2(f)
describe formation of esters by reaction of alcohols with carboxylic acids and concentrated H₂SO₄ as catalyst as exemplified by ethanol
16.1.3(a)-i
classify alcohols as primary, secondary and tertiary alcohols
16.1.3(a)-ii
classify alcohols as primary, secondary and tertiary alcohols, to include examples with more than one alcohol group
16.1.3(b)
state characteristic distinguishing reactions of primary, secondary and tertiary alcohols, e.g. mild oxidation with acidified K₂Cr₂O₇, colour change from orange to green
16.1.4
deduce the presence of a CH₃CH(OH)– group in an alcohol, CH₃CH(OH)–R, from its reaction with alkaline I₂(aq) to form a yellow precipitate of tri-iodomethane and an ion, RCO₂–
16.1.5
explain the acidity of alcohols compared with water