Topic 7 National 4 & 5 Chemistry Summary Notes. Hydrocarbons

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1 Topic 7 National 4 & 5 Chemistry Summary Notes Hydrocarbons A vast number of different hydrocarbons exist and so chemists have grouped them into sub-sets to make them easier to study. In this topic we will study three different hydrocarbon sub-sets. LI 1 The Alkanes The alkanes make up the simplest sub-set of all the hydrocarbons. Most of the FUELS we use are made from alkanes. They are also useful starting materials for a huge range of other substances such as PLASTICS and DRUGS. Name of Alkane Methane propane butane octane Uses (natural gas) for cooking, heating Used in gas cylinders in homes Sold in blue cylinders as camping gas A component of petrol All the alkanes end in ANE. A prefix tells you how many carbon atoms are present in the molecule. Prefix Number of Carbon Atoms Meth 1 Eth 2 Prop 3 But 4 Pent 5 Hex 6 Hept 7 Oct 8 The alkanes all contain COVALENT bonds. They are different from other compounds since they are able to form long, chain like molecules containing many carbon atoms joined together. 1

2 Physical State of Alkanes Name of Alkane Boiling Point (⁰C) Physical State at Room Temperature (25⁰C) Methane Ethane Propane Butane Pentane Hexane Heptane Octane *Complete the table using the data book pg LI 2 General Formula for the Alkanes If you look at the full structural formula for the alkanes you should see that there is a pattern. Each carbon atom is joined to two hydrogen atoms with two extra hydrogens at the end of the molecule. This gives the general formula in mathematical terms as: Where n = the number of carbon atoms in the molecule 2

3 LI 3 Drawing and Naming Alkanes We can represent the alkanes in a variety of different ways: Molecular Formula This is the simplest type of formula used for alkanes and other hydrocarbons. This type of formula shows only the number of carbon and hydrogen atoms present. e.g. ethane C 2 H 6 Full Structural Formula The full structural formula gives a simplified picture of the structure of the molecule. All the bonds present between the carbon atoms and the carbon and hydrogen atoms are shown. e.g. ethane Shortened Structural Formula This type of formula shows how many CH 2 and CH 3 groups are present in the molecule. e.g. ethane CH 3 CH 3 propane CH 3 CH 2 CH 3 3

4 ALKANE MOLECULAR FORMULA FULL STRUCTURAL FORMULA SHORTENED STRUCTURAL FORMULA Methane CH 4 Ethane C 2 H 6 Propane C 3 H 8 4

5 Butane C 4 H 10 Pentane C 5 H 12 Hexane C 6 H 14 *The names and molecular formulae of the first eight alkanes are 5 found in the data book pg

6 LI 4 Saturation and Unsaturation All the carbon to carbon bonds in the alkanes are single C-C bonds. For this reason they are described as being SATURATED molecules. In other hydrocarbon families not all the carbon to carbon bonds are single C-C bonds and are therefore described as being UNSATURATED molecules. ALKANES ARE SATURATED MOLECULES LI 5 Homologous Series A HOMOLOGOUS SERIES is a family of compounds with similar chemical properties and can be represented by a general formula. The alkanes form a homologous series because they share the following characteristics: they all fit the same general formula they all have similar chemical properties i.e. they all burn they show a gradual change in physical properties as the molecules get bigger in size e.g. boiling point increases as molecular size increases. LI 6 Reactions of Alkanes Apart from COMBUSTION the alkanes undergo few other reactions. Alkanes burn in a plentiful supply of oxygen to produce carbon dioxide and water. alkane + oxygen carbon dioxide + water e.g. CH 4 + 2O 2 CO 2 + 2H 2 O It is for this reason that the alkanes are mainly used as FUELS. 6

7 LI 7 The Alkenes The alkenes are another homologous series of hydrocarbons containing covalent bonds. Alkenes are similar to alkanes in many ways but the main difference is the presence of the carbon-to-carbon double bond in alkenes, represented as C=C. All alkenes end in ENE and the first member of the family is ethene. Can you think why there is no methene? Each alkene contains only one C=C *Each carbon atom only forms 4 bonds so be careful not to add too many hydrogen atoms when drawing full structural formula! Since the alkenes are not full of carbon to carbon single bonds they are described as being UNSATURATED molecules. ALKENES ARE UNSATURATED MOLECULES General Formula for the Alkenes All alkenes fit the same general formula. It should be easy to see a pattern as the number of carbon atoms increase. Where n = the number of carbon atoms in the molecule 7

8 ALKENE MOLECULAR FORMULA FULL STRUCTURAL FORMULA SHORTENED STRUCTURAL FORMULA Ethene C 2 H 4 Propene C 3 H 6 Butene C 4 H 8 8

9 Pentene C 5 H 10 Hexene C 6 H 12 Heptene C 7 H 14 9

10 Uses of Alkenes The C=C present in alkenes is very reactive compared to the C-C in alkanes. The C=C allows alkenes to be changed readily into new products e.g. ethene and propene are used in the plastics industry to make polyethene and polypropene. Alkenes are very important feedstocks for the PLASTICS INDUSTRY. LI 8 Reactions of Alkenes 1.Combustion Like all other hydrocarbons the alkenes burn in a plentiful supply of oxygen to produce carbon dioxide and water. alkene + oxygen carbon dioxide + water e.g. C 2 H 4 + 3O 2 2CO 2 + 2H 2 O 2. Addition Reactions The C=C is a reactive bond which breaks easily. This means that small molecules can add across the double bond, usually with the help of a catalyst e.g. a) Addition of Hydrogen (H 2 ) Two hydrogen atoms add across the C=C to form the corresponding ALKANE. e.g. ethene + hydrogen ethane 10

11 b) Addition of Bromine (Br 2 ) ethene + bromine 1,2-dibromoethane Using Bromine Water to Test for Unsaturation A solution of bromine water Br 2 (aq) can be used to distinguish an alkene from an alkane. Bromine water is an ORANGE colour but when bromine reacts with an ALKENE, the product of the reaction is COLOURLESS. We say that the bromine has been DECOLOURISED. Br 2 Br Br ethene bromine (orange) 1,2-dibromoethane (colourless) ALL ALKENES QUICKLY DECOLOURISE BROMINE WATER ALKANES DO NOT REACT WITH BROMINE WATER 11

12 Colour the boxes below to show the effects of bromine water reacting with: a) an alkane + alkane bromine water stays orange (colourless) (orange) b) an alkene + alkene bromine water decolourises (colourless) (orange) LI 9 N5 The Cycloalkanes The CYCLOLKANES are another homologous series of hydrocarbons in which the carbon atoms are joined to form RINGS. Cycloalkanes are full of C-C single bonds and are therefore SATURATED compounds. They will not decolourise bromine water. The first member of the cycloalkanes is CYCLOPROPANE. The cycloalkanes all fit the same general formula: Where n = the number of carbon atoms 12 in the molecule

13 CYCLOALKANE MOLECULAR FORMULA FULL STRUCTURAL FORMULA SHORTENED STRUCTURAL FORMULA Cyclopropane C 3 H 6 Cyclobutane C 4 H 8 Cyclopentane C 5 H 10 13

14 LI 10 Branched Chain Alkanes Alkanes like propane and butane are described as STRAIGHT CHAIN ALKANES because each carbon atom is joined to no more than 2 other carbon atoms. However, crude oil and natural gas both contain another type of alkane called BRANCHED CHAIN ALKANES. In these alkanes some carbon atoms are joined directly to three or four carbon atoms. e.g. bbkfsdokfosdf Straight chain Branched chain Branched chain Rules for Naming Branched Chain Alkanes 1. Look for the longest continuous chain of carbon atoms and name after the parent alkane. 2. Number the carbon atoms in the longest chain from the end which gives the lowest numbers to the carbon atoms that have branches attached. 3. Identify the groups making up the branches ( known as alkyl groups). Alkyl Group Name of branch -CH 3 methyl -C 2 H 5 or CH 2 CH 3 ethyl -C 3 H 7 or CH 2 CH 2 CH 3 propyl 4. Use the prefixes di-, tri-, tetra etc. to indicate how many of a particular branch are present. 5. Indicate the position of each branch with a number placed in front of its name. 6. If more than one type of branch is present, the names are put in alphabetical order e.g. ethyl would come before methyl. 14

15 Examples: LI 11 Isomers Isomers are compounds with the same MOLECULAR FORMULA but a different STRUCTURAL FORMULA. Butene and cyclobutane are ISOMERS. These two compounds have the same number of carbon and hydrogen atoms but they are arranged differently. Butene contains a C=C whereas cyclobutane does not. 15

16 *Isomers of straight chain alkanes can be branched alkanes. *Isomers of alkenes can also be produced by moving the position of the C=C in molecules with 4 or more carbon atoms. But-1-ene 16 But-2-ene

17 *Note the different positions of the Cl atoms in the two isomers. 17

18 N4 Cracking In oil refineries, the fractional distillation of crude oil generally produces more long chain alkanes than are needed by industry. A process called CRACKING breaks down the long chain alkanes into smaller, more useful molecules which are in greater demand. When a long chain alkane is cracked it produces a mixture of ALKANES and ALKENES. Alkenes are very useful in the plastics industry. e.g. cracking of decane C 10 H 22 C 6 H 14 + C 4 H 8 decane hexane butene (saturated) (unsaturated) When an alkane is cracked there are not enough hydrogen atoms to produce two alkanes and so one product is an unsaturated alkene. When an alkane is cracked the carbon chain may break at different points on different molecules which means a mixture of products is usually obtained. 18

19 Cracking in the Lab aluminium oxide catalyst delivery tube water Cracking can be carried out in the lab using an aluminium oxide catalyst. To prevent suck back the delivery tube should be removed from the water before heating stops. To prove the gas is an alkene, bromine water can be added to the test tube of product gas. The gas decolourises the bromine water. CRACKING is a process used to meet the demand for shorter chain alkanes and alkenes. 19

20 National 4 & 5 Topic 7 Hydrocarbons Number Learning Intention Success Criteria 1 I will find out about the simplest subset of hydrocarbons known as the Alkanes I can: State uses for some alkanes State the physical states of alkanes at room temperature State that alkanes contain covalent bonds State that all alkanes end in ANE. State that a prefix indicates the number of carbon atoms in the molecule. Name the first eight members of the alkanes 2 I will work out the general formula for the Alkanes after completion of LI3 3 I will find out how to represent alkanes in a variety of ways 4 I will find out the difference between saturated and unsaturated molecules 5 I will find out about the meaning of a homologous series. I can: State the general formula for the alkanes as C n H 2n+2 State that n = a whole number I can: State what is meant by molecular formula, shortened structural formula and full structural formula. Represent the first eight members of the alkane family using molecular formula, shortened structural formula and full structural formula I can: State that saturated molecules are full of C-C single bonds State that unsaturated molecules contain a C=C State that the alkanes are saturated molecules I can : State that all members of a homologous series can be represented by 20

21 6 I will find out about the different types of reactions alkanes undergo 7 I will find out about another homologous series of hydrocarbons called the alkenes 8 I will find out about the reactions the alkenes can undergo 9 I will find out about the homologous series of cycloalkanes I can: I can I can I can: a general formula State that all members have similar chemical properties State that there is a gradual change in physical properties as the molecules get bigger in size e.g. boiling point increases State that all alkanes burn and are used mainly as fuels Write and balance combustion formulae equations for alkanes State that alkenes contain one C=C per molecule Represent the first 6 members of the alkenes using molecular formula, shortened structural formula and full structural formula. Work out the general formula for the alkenes and state this as C n H 2n State that alkenes are important feedstocks for the plastics industry. State that all alkenes burn to produce CO 2 and H 2 O State that alkenes undergo addition reactions due to the presence of the C=C State that small molecules can add across the C=C Draw the products of addition reactions State that alkenes decolourise bromine water whereas alkanes do not. State that alkenes are unsaturated molecules State that bromine water is used as the standard test for unsaturation State that the cycloalkanes are hydrocarbons made up of rings of carbon atoms State that cycloalkanes do not react with bromine water and are therefore saturated compounds State the general formula as C n H 2n 21

22 10 I will learn how to recognise and name branched chain alkanes 11 I will find out the definition of an isomer and how to draw isomers I can: I can: 12 I will carry out a cracking experiment I can: Represent the first 5 members of the cycloalkanes using molecular formula, shortened structural formula and full structural formula. Differentiate a straight chain alkane from a branched chain alkane Follow a set of rules to name a branched chain alkane State the definition of an isomer Draw isomers of straight chain alkanes State that alkenes are isomers of cycloalkanes i.e. cyclopropane is an isomer of propene Draw isomers of alkenes with 4 or more carbon atoms by moving the position of the C=C State that cracking is a process used to meet the demand for shorter chain alkane and alkenes. 22

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