Form 5 Chemistry Notes Ms. R.

Buttigieg

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Topic 2 Organic Chemistry

Organic Chemistry is the chemistry of compounds, which are found in living things or are derived from living things. The basis of these molecules is carbon chains or rings.
A Homologous series is a family of compounds. E.g. Alkanes, alkenes, alkynes, alcohols, fatty acids. Members of a series have: 1. Same general molecular formula, each member differing from the next by CH2. 2. Similar chemical reactions 3. All possess the same functional group 4. Physical properties of members change gradually in the same direction along the series. e.g. melting points and boiling points and density rise as molecular mass increases. Alkanes (CnH2n+1) See GCSE pg. 175, C4U pg. 159 1. Alkanes are hydrocarbons. 2. They have only single bonds between carbon atoms. 3. b.p and m.p. and density increase with chain length i. C1 to C4 are gases at room temperature ii. C5 to C15 are liquids iii. C16 upwards are solids 4. They are volatile compared to ionic compounds. E.g. tar with RMM>500 melts on hot days While NaCl with RMM of 58.5 melts at 808oC 5. Alkanes are found in natural gas and crude oil. 6. Insoluble in water. 7. Soluble in organic solvents like benzene and tetrachloromethane (CCl4) 8. Very unreactive due to strong C-C and C-H bonds. 9. Do not react with metals, aqueous oxidising agents, acids or alkalis. 10. Burn. Combustion is very exothermic so used as fuels. CH4 (g) + 2 O2 (g) CO2 (g) + 2H2O (l)

Make sure you can draw Methane to decane structures

When there is little oxygen, C and CO form as well as CO2. CO is poisonous so a danger.

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11. Alkanes react with halogens by substitution reactions.

This reaction is catalysed by light (U.V.) and is explosive in bright sunlight. The reaction is slower with bromine. Nothing happens with iodine.

12. Alkanes readily decompose when they are strongly heated, the higher members splitting more readily. This is the basis of cracking. Cracking helps to produce more petrol. High temperatures are used and a catalyst, finely divided aluminium oxide and silicon (IV) oxide speed up the reaction.

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The products of crude oil, which are produced by a specific number of carbon atoms in a hydrogen chain at a particular temperature, are given in this table:

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Answer the following: 1. Which one of the following compounds is not a hydrocarbon? C2H4 C6H12 C2H6O C7H16 C6H6 C10H22 C4H10 C40H82

2. Which one of the compounds below isnt an alkane?

3. Write down a use for each of the following alkanes a. methane: ______________________________________________________________________ b. propane: ______________________________________________________________________ c. octane: _______________________________________________________________________ 4. Write down the equations for burning of: a. methane: ______________________________________________________________________ b. propane: ______________________________________________________________________

Saturated Compounds contain only single bonds between carbon atoms. So alkanes are
saturated hydrocarbons. Compounds which have double or triple bonds between carbon atoms are said to be unsaturated. E.g. alkenes and alkynes. They are called saturated as more atoms can be added to the molecules. Isomers compounds which have the same molecular formula but a different structural formula. E.g. Butane Isobutane

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ETHENE A colourless gas Insoluble in water. It has a faint sweet smell, About the same density as air Burns with a yellow flame (luminous flame) Decolourises bromine water and acidified potassium permanganate. Produced industrially by cracking heavier fractions from crude oil. Laboratory preparation of ethene

Ethene is produced by the dehydration of ethanol by hot, concentrated sulphuric acid. 100cm3 of concentrated sulphuric acid (excess is used) are mixed with 50cm3 of ethanol. This is done slowly and while cooling under running cold water as when the sulphuric acid is mixed with ethanol, a lot of heat is given out. Then some sand (acid washed) is placed in the flask so that the ethene forms on the sand and so avoid frothing. The contents are then heated on a sand-bath to about 180oC. The ethene given off is passed through sodium hydroxide solution to remove impurities (sulphur dioxide and carbon dioxide) and collected over water. The liquid darkens in the flask due to carbon formed by charring.

C2H5OH (aq) + H2SO4 (aq) C2H5OH - H2O

C2H5HSO4 (aq) + H2O (l) C2H4

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JL Annual 2006 - Section 1

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Properties of Alkenes (taking ethene as example)

1. More reactive than alkanes due to unstable Carbon-Carbon double bond. 2. Undergo addition reactions due to their double bond. a. With Hydrogen A nickel catalyst at 150oC. Called Sabatiers Reaction Used in hardening oils to make margerine Oils are solidified by reacting them with hydrogen. increases they solidify. This is also called a hydrogenation reaction as hydrogen is added. As their RMM

Ethene

Hydrogen

Ethane

b. With water - e.g. Ethene

With water ethanol is formed. This is the industrial preparation of ethanol. Takes place at 300oC, 60 atm and over a catalysts of phosphoric acid.

Ethene

water

ethanol

3. Ethene is oxidised with acidified or alkaline potassium permanganate

C2H4 + H2O + [O]

CH2OH. CH2OH

Ethan-1,2-diol is used as a coolant in aircraft engines, an antifreeze solution for motor car radiators and in the production of terylene.

4. Ethene burns. C2H4 (g) + 3 O2 (g)

2 CO2 (g) + 2 H2O (g)

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5. Ethene can undergo polymerisation. This happens when molecules of ethene add on to each other to form giant molecules of poly-ethene or polythene. Polythene is a white solid. High temperatures and pressure are needed and a catalyst (trace of oxygen)

6. Ethene is used: to make plastics (polythene, terylene, polystyrene, PVC), ethanol (in methylated spirits), and 1,2-dibromoethane (an important additive in petrol).
JL2006 annual

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Alkynes
These are hydrocarbons which have a triple bond between 2 of the carbon atoms.

Physical properties 1. They are insoluble in water. 2. They are quite soluble in the usual organic solvents of low polarity (e.g. ligroin, ether, benzene, carbon tetrachloride, etc.). 3. They are less dense than water. 4. Their boiling points show the usual increase with increasing carbon number. 5. They are very nearly the same as the boiling points of alkanes or alkenes with the same carbon skeletons. Chemical properties They burn in air to produce carbon dioxide and water . The ethynes are highly dangerously explosives when mixed with air or oxygen.

They undergo addition reactions.

Naming alkynes

Number of Carbons Ethyne

Chemical formula

Structural formula

Propyne

Butyne

The alkynes are said to be unsaturated because of the existence of a multiple bond in the molecule. The general structure of the alkyne series of hydrocarbons is CnH2n-2.

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1. Copy and complete the following on the HW copybook.

Hydrocarbons are compounds containing the elements _______________ and ______________. If they are saturated, the atoms of carbons are bound together by _________________ bonds. On the other hand, unsaturated hydrocarbons include at least one _______________ or _______________ bond. One example of unsaturated hydrocarbons is _________________. This compound burns in a plentiful supply of air to produce ________________________ and _________________. It also reacts with bromine water changing the colour of the solution from _________________ to _________________. (5 marks) 2. The statements below describe the chemistry of carbon and some of its compounds. Write brief notes to show that you understand the meaning of these statements with particular reference to the underlined terms.

3. This question concerns the laboratory preparation of ethene and its properties.

a) Ethene can be prepared in the laboratory by dehydration of ethanol. Explain this statement, including essential conditions and an equation for the reaction. (A diagram is not required). (6 marks)

b) Ethene undergoes a number of addition reactions such as halogenation, hydration and hydrogenation. For each of these addition reactions, (i) name the substance that adds on the ethene, (ii) give an equation for the reaction. (9 marks) c) Ethene burns with a smoky flame. Give a reason for this observation and write an equation for the reaction. (3 marks) d) Give two uses of ethene. (2 marks)

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Alcohols (see Chemistry for You pg. 178 182, GCSE pg. 203)
These contain the OH group. The OH group hydroxyl group does not form hydroxide ions in solution. Alcohols are NOT alkaline. Naming alcohols Number of Carbons Methanol Chemical formula Structural formula

Ethanol

Propanol

Alcoholic drinks contain ethanol. Thats what makes them alcoholic. So beer, wine and whisky all contain ethanol. If alcohol is taken in excess it: Slows down our reactions Makes us overconfident Damages the liver Is addictive Laboratory Preparation of Ethanol - by fermentation Sugar is dissolved in water. Some yeast is added. The mixture is put in a conical flask. A delivery tube leads to a test-tube containing calcium hydroxide solution (lime-water). The flask is left in a warm place for several days. The contents in the flask begin to froth. A gas is given out. When it is bubbled through the calcium hydroxide solution, this turns milky, indicating it is carbon dioxide. C12H22O11 (s) + H2O (l) sugar C6H12O6 (aq) 2 C6H12O6 (aq) glucose

2 C2H5OH (aq) + 2 CO2 (g)

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These two reactions happen through the action of yeast. After several days the contents are found to contain between 5 and 10% ethanol. Pure ethanol can be obtained by fractional distillation. Ethanol can be tested by burning as it burns easily with a pale yellow flame. Industrial Preparation of Ethanol Ethene is reacted with steam to form ethanol.
o

C2H4 (g) + H2O (l)

C2H5OH (aq)

Temp: 300 C Pressure: 65 atm Catalyst: Phosphoric Acid Properties of Ethanol 1. Miscible with water 2. Colourless liquid (b.p. 78oC) 3. Very good solvent for molecular substances 4. Burns very easily with a pale yellow flame C2H5OH (l) + 3 O2 (g) 2 C2H5OH (l) + Na (s) is ionic: C2H5O- Na+ 6. Ethanol reacts with phosphorus pentachloride, PCl5 C2H5OH (l) + PCl5 (l) C2H5Cl (g) + POCl3 (l) + HCl (g) It is a vigorous reaction in which steamy fumes of hydrogen chloride are formed. 7. Ethanol reacts with concentrated sulphuric acid that acts as a dehydrating agent. a. If it is in excess at a temperature of 180oC C2H5OH - H2O 2 molecules of ethanol. 2 C2H5OH - H2O C2H5OC2H5 ethoxyethanoate C2H4 b. If it is in excess at a temperature of 145oC only 1 molecule of water is extracted from 2 CO2 (g) + 3 H2O (l) 2 C2H5ONa (aq) + H2 (g)

5. Ethanol reacts with sodium. Hydrogen gas is given off.

If the excess ethanol is evaporated, sodium ethoxide is obtained as a white solid. Sodium ethoxide

Work these out on your copybook - Chemistry For You Pg. 185 numbers 1, 2 Pg. 254 numbers 11, 14, 15; Pg. 255 numbers 16, 19

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8. Ethanol reacts with ethanoic acid to form an ESTER C2H5OH (l) + CH3COOH (l) CH3COOC2H5 (l) + H2O (l)

To make an ester, we use: 4 cm3 of ethanol 2 cm2 ethanoic acid, some concentrated sulphuric acid some antibumping granules. The contents are heated under reflux in a water bath for 25 minutes, then poured in a brine solution. Oily drops are seen on the surface smelling of pear drops. This is the ester ethyl ethanoate. 9. Ethanol can be oxidised to ethanoic acid, if we use acidified potassium dichromate as an oxidising agent. The ethanol is oxidised to ethanoic acid. C2H5OH (l) + 2 [O] The orange potassium dichromate turns to green. The experiment is performed in the following way: Mix ethanol with acidified potassium dichromate. Heat under reflux for 15 minutes. Fractionally distillate the contents to obtain ethanoic acid. Wine goes sour as the ethanol in it is oxidised to ethanoic acid (vinegar). The oxidation is catalysed by enzymes in the wine, using oxygen from the air Esters have a pleasant fruity smell. They are found in fruit, flowers and are used in perfumes. Fats are complex esters. CH3COOH (l) + H2O (l)

See GCSE Chemistry, page 208, 209 pg. 208 no. 2 Work out Pg. 276 no. 76 Pg. 277 no. 78, 80

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Number of Carbons 1

Alkanes

Alkenes

Alkynes

Organic Acids
An organic compound is an acid if it has the COOH group. This COOH is called a carboxyl group. Acid Ethanoic acid Chemical formula Chemical Structure

Propanoic Acid.

Properties 1. These acids are weak acids. i.e. they are not fully dissociated in solution. CH3COOH (aq) CH3COO- (aq) + H+ (aq)

2. When pure they are not acidic, since it is in water that they break up into ions. 3. Ethanoic acid is a weak electrolyte. Like all acids, it reacts with metals, alkalis and carbonates. 2 CH3COOH (aq) + Ca (s) CH3COOH (aq) + NaOH (aq) 2 CH3COOH (aq) + Na2CO3 (s) (CH3COO)2 (aq) + H2 (g) CH3COONa (aq) + H2O (g) 2CH3COONa (aq) + CO2 (g) + H2O (g)

Laboratory preparation of ethanoic Acid see previous page oxidation of ethanol

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Synthetic Polymers
These can be either addition or condensation polymers.

Addition Polymers Polystyrene poly(phenyl ethene)

Perspex

Note: The above are addition polymers. Units are added together as the monomers are unsaturated. The polymer than gives a saturated product.

Condensation Polymers Nylon

Terylene

Note: i. Formation of the above polymers requires two types of monomer molecules, each with two reactive groups. ii. Each time a bond is formed, a small molecule such as water is removed.

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Answer the following questions: 1. The following represent two monomers, which react together to form a polymer. H2N - NH2 COOH - COOH

a. Name the type of polymerisation ______________________________ b. What is the substance lost during polymerisation ________________________ c. Draw a diagram to show the structure of the polymer formed from, at least three monomers.

d. Give the name of one example of this type of polymer. ______________________ e. Another type of polymer, poly(chloroethene), is formed by the polymerisation of chloroethene. The following diagram represents part of the poly(chloroethene chain). - CH2 CH CH2 CH CH2 CH CH2 CH | | | | Cl Cl Cl Cl Draw a diagram to represent a single molecule of chloroethane

JL Annual 2001 Past paper questions related to organic chemistry 2

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JL Annual 2002 Past paper questions related to organic chemistry 3

JL Annual 2001 Past paper questions related to organic chemistry 4