How do we name, classify and predict the reactions of the simplest hydrocarbons?
Nomenclature and isomerism, the reactions of alkanes (combustion and free-radical substitution), and the reactions of alkenes (electrophilic addition and addition polymerisation) including Markownikoff's rule.
An Edexcel 9CH0 Topic 6 answer covering organic nomenclature and isomerism, alkane combustion and free-radical substitution, and alkene electrophilic addition and addition polymerisation.
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What this topic is asking
Edexcel Topic 6 wants you to name and classify organic compounds, recognise the types of structural and stereo isomerism, and describe and explain the reactions and mechanisms of alkanes (combustion and free-radical substitution) and alkenes (electrophilic addition and addition polymerisation), applying Markownikoff's rule.
The answer
Nomenclature and isomerism
Compounds are named from the longest carbon chain (the stem: meth, eth, prop, but), a suffix for the functional group (-ane, -ene, -ol), and prefixes with locant numbers for substituents, chosen to give the lowest set of numbers.
Alkane reactions
Alkanes are saturated and fairly unreactive (strong, non-polar and bonds). They undergo:
- Complete combustion to and in plenty of oxygen.
- Incomplete combustion to (toxic) or soot when oxygen is limited.
- Free-radical substitution with halogens in UV light, by a three-stage mechanism: initiation (homolytic bond fission of forming radicals), propagation (chain-carrying steps that regenerate a radical), and termination (two radicals combine to end the chain).
Alkene reactions
The double bond is electron-rich (a pi bond above and below the sigma bond) and attracts electrophiles, so alkenes undergo electrophilic addition with (the test for unsaturation, orange to colourless), , and (steam with a phosphoric acid catalyst, to make alcohols).
Alkenes also undergo addition polymerisation, in which many monomers join by opening the bond, with no other product, for example (poly(ethene)). This has atom economy.
Examples in context
Example 1. Cracking crude oil for petrol and plastics. Long-chain alkanes from crude oil are catalytically cracked into shorter alkanes (for fuels) and alkenes such as ethene and propene. The alkenes are then used in addition polymerisation to make poly(ethene) and poly(propene). This connects the alkane and alkene chemistry of Topic 6 to the petrochemical industry, where the reactive of the cracked alkenes is the gateway to plastics.
Example 2. The bromine water test in the field. Field chemists and students test for unsaturation by shaking a sample with orange bromine water: an alkene decolourises it rapidly (electrophilic addition across the double bond), while an alkane does not react in the dark. This simple, vivid test distinguishes saturated from unsaturated hydrocarbons and is a direct application of the difference in reactivity between the single bond and the double bond.
Try this
Q1. Name the three stages of the free-radical substitution mechanism. [3 marks]
- Cue. Initiation, propagation, termination.
Q2. Predict the major product of the reaction between propene and hydrogen bromide, and explain your choice. [3 marks]
- Cue. 2-bromopropane; Markownikoff's rule, formation of the more stable secondary carbocation.
Exam-style practice questions
Practice questions written in the style of Pearson Edexcel exam questions on this dot point, with worked answer explainers. The year tag is the paper they imitate, not the source.
Edexcel 20185 marksMethane reacts with chlorine in the presence of ultraviolet light. (a) Name the type of mechanism. (b) Write equations for the initiation step and for the two propagation steps. (c) Give one termination step.Show worked answer β
Show homolytic fission and the chain-carrying radicals.
(a) Free-radical substitution (1).
(b) Initiation: (homolytic fission) (1). Propagation 1: (1). Propagation 2: (1).
(c) Termination (any radical-radical combination), e.g. , or , or (1).
Edexcel 20214 marksBut-1-ene reacts with hydrogen bromide. (a) State and explain, using carbocation stability, which is the major product. (b) Outline the mechanism, naming it and showing the curly arrows.Show worked answer β
Apply Markownikoff's rule via the more stable carbocation, then give the mechanism.
(a) The major product is 2-bromobutane (1). Markownikoff addition forms the more stable secondary carbocation rather than the less stable primary one, and the then bonds to that carbon (1).
(b) Electrophilic addition (1). The pi electrons attack the H of (curly arrow from the double bond to H, and from the bond to Br), forming a secondary carbocation and ; the bromide ion's lone pair then attacks the carbocation (curly arrow from to the positive carbon) to give 2-bromobutane (1).
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Sources & how we know this
- Pearson Edexcel A-Level Chemistry (9CH0) specification β Pearson Edexcel (2015)