Organic Chemistry I
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6.1 Hydrocarbons, homologous series and formulae
A hydrocarbon contains hydrogen and carbon only. Saturated means only single C–C bonds; unsaturated means at least one C=C.
A homologous series is a family of compounds with the same functional group and general formula, in which each member differs from the next by CH2. Members have similar chemical properties and a gradual trend in physical properties.
A functional group is the atom or group of atoms responsible for the characteristic reactions of a compound.
| Formula type | Butane |
|---|---|
| Molecular | C4H10 |
| Empirical | C2H5 |
| General | CnH2n+2 |
| Structural | CH3CH2CH2CH3 |
| Displayed | Every atom and every bond drawn |
| Skeletal | Zig-zag line; each corner and end is a carbon; H on C not shown |
Check yourself: What is the general formula of the alkanes?
CnH2n+2
6.2 Naming organic compounds (IUPAC)
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6.3 Isomerism
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6.4 Types of reaction and bond breaking
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6.5 Alkanes and crude oil
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6.6 Combustion, pollution and alternative fuels
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6.7 Radical substitution of alkanes
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6.8 Alkenes: bonding and addition reactions
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6.9 Electrophilic addition mechanisms
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6.10 Addition polymers
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6.11 Halogenoalkanes and nucleophilic substitution
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6.12 Rates of hydrolysis of halogenoalkanes
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6.13 Alcohols
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6.14 Oxidation of alcohols
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6.15 Preparing and purifying a liquid organic compound
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Extra worked questions
Cover the solution, answer on paper, then mark yourself against each step. Each step shows the mark it earns.
All 8 worked solutions are free for members. The first one is open to everyone.
Naming two compounds
Name (a) CH3CH(CH3)CH2CH3 and (b) CH3CHClCH2CH3.
Try it first, then show the worked solution
| (a) | Longest chain is four carbons with a methyl on C2: 2-methylbutane | 1 |
|---|---|---|
| (b) | Four-carbon chain, Cl on C2 (counting from the nearer end): 2-chlorobutane | 1 |
Answer: (a) 2-methylbutane (b) 2-chlorobutane
Examiner tip: Look for the longest chain even if it bends round a corner in the way the formula is written.
Testing for an alkene
Describe the test for a C=C double bond and give the equation for the reaction with ethene.
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E and Z isomers
1-chloropropene, CH3CH=CHCl, has two stereoisomers. Explain why, and identify which isomer has the CH3 and Cl on the same side.
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Which hydrolyses fastest?
1-chlorobutane, 1-bromobutane and 1-iodobutane are warmed with aqueous silver nitrate in ethanol. Predict the order in which precipitates appear and explain it.
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Reactions of propan-2-ol
Give the reagent and the organic product for converting propan-2-ol into (a) 2-chloropropane, (b) 2-bromopropane and (c) propene.
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Propene with hydrogen bromide
Propene reacts with HBr to give two products. Name the major product and explain why it is formed in greater amount.
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Mechanism: chlorine and methane
Give the mechanism for the reaction of methane with chlorine in UV light to form chloromethane. Name each stage.
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Core Practical 6: yield and purification
10.0 cm3 of 2-methylpropan-2-ol (density 0.786 g cm−3, M = 74.0) is shaken with excess concentrated HCl, giving 7.40 g of pure 2-chloro-2-methylpropane (M = 92.5). (a) Calculate the percentage yield. (b) Explain the purpose of the sodium hydrogencarbonate wash and of anhydrous sodium sulfate.
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Video walkthroughs
Narrated walkthroughs of exam-style questions from this topic of the book, showing where each mark comes from. Try the question first, then watch. Captions are available in the player.
Radical substitution of ethane
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Electrophilic addition of HBr to propene
Hydrolysis rates of halogenoalkanes
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Making 2-chloro-2-methylpropane
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Identifying a tertiary alcohol
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Recall cards
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