Chapter 11

Carbon Compounds

Carbon Compounds Usually contain CARBON and HYDROGEN only or CARBON and HYDROGEN with other non-metal elements (Oxygen, Nitrogen, Sulphur, Phosphorus and Halogens). Can be classified into two groups : Organic Compounds + Inorganic Compounds Organic Compounds All carbon-containing compounds are organic compounds EXCEPT oxide of carbon and carbonate. Eg. Nylon, Protein, Petrol, Plastic, Cellulose, Fat, Starch, Alcohol, Carboxylic Acid Combustion :- Complete Combustion (EXCESS oxygen) : [Organic Compounds + O2 CO2 + H2O] - Incomplete Combustion (LIMITED oxygen) : [Organic Compounds + O2 C / CO + H2O] - More smoke is produced in the incomplete combustion than the complete combustion. Inorganic Compounds All non carbon-containing compounds + Few carbon-containing compounds (oxide of carbon and carbonate) Eg. Carbon monoxide, Potassium Cyanide, Sodium Carbonate, Aluminium Carbide. Hydrocarbon The most common natural sources of hydrocarbons are petroleum and natural gas. Eg. Alkane, Alkene. SINGLE covalent bonds / DOUBLE covalent bonds / TRIPLE covalent bonds (Carbon - Other elements) Can be classified into two groups :Saturated (only single covalent bonds) + Unsaturated (at least one double or triple covalent bond) Non-hydrocarbon Eg. Alcohol, Carboxylic Acd, Ester, Fat, Natural Rubber

Carbon Compounds Organic Compounds Hydrocarbons Saturated Hydrocarbons Unsaturated Hydrocarbons Nonhydrocarbons Inorganic Compounds

Physical Properties Comparison Among All The Organic Compounds Organic Compounds Colour Physical State Alcohol All are colourless (1 12) Number of carbon 1 12 : Liquid > 12 : Solid Carboxylic Acid Ester Colourless Volatile compound

Melting and Boiling Point

All are colourless Number of carbon 1 10 : Liquid > 10 : Solid Higher than corresponding alkane, alkene and alcohol Carboxyl group contains two types of bonds double bond and single bond. Increase when going down the group Number of carbon atoms in the molecule increase. Thus, the molecular size of increases and the weak Van der Waals force of attraction between the molecules become stronger. Thus, more energy is required to overcome the strong Van der Waals force of attraction when going down the group.

Lower than corresponding alcohol and carboxylic acid.

Increase when going down the group Density The relative molecular mass of the molecule increase and molecules are packed more closely together. The hydroxyl part is soluble in water but the hydrocarbon part insoluble in water When the effect of the hydroxyl part on solubility is greater than the effect of the hydrocarbon parts = soluble in water (1 3 : soluble > 4 : insoluble

Solubility (Water)

The carboxyl part is soluble in water but the hydrocarbon part insoluble in water When the effect of the carboxyl part on solubility is greater than the effect of the hydrocarbon parts = soluble in water (1 4 : soluble > 5 : insoluble

Insoluble (will form an oily layer on water)

Solubility (Organic Solvent [Benzene]) Electrical Conductivity d

Soluble

Alkanes (C2H2n+2, n = 1, 2, 3 ) Unreactive compounds because they are saturated compounds as the STRONG carbon-carbon and carbon-hydrogen single bonds must be broken for the alkanes to react. Neutral compounds and have no effect on red or blue litmus paper plus do not react with acid or alkali. Chemical Properties :(a) Combustion (Complete and Incomplete) - Large quantities of heat are liberated, making it suitable to be used as a fuel. - When the number of carbon atom per molecule increases, the alkanes produces more heat and become less flammable - more difficult to burn [as the molecular size of the alkane molecule increases] plus the flame becomes more smoky [as the percentage of carbon in the alkane molecule increases]. (b) Halogenation [Exposed to ultraviolet light / sunlight] - Carbon-hydrogen bonds are broken and new carbon-halogen bonds are formed. - When a mixture of alkane and halogen is exposed to ultraviolet light or sunlight, a reaction in which the hydrogen atoms in alkane are replaced step by step by halogen atoms. - Replaced by chlorine : Chlorination Replaced by bromine : Bromination - Rate of reaction (ALKANE & BROMINE) slower than rate of reaction (ALKANE & CHLORINE) Because chlorine has a higher position in electrochemical series. - Iodine does not react with alkanes as the reaction is too slow. Alkenes (C2H2n, n = 2, 3, 4 ) Very reactive compounds because they are unsaturated compounds as the carbon-carbon double bonds is very easy to be broken and react with others. For alkene molecules containing three or more carbon atoms, the position of the double bond must be specified. Chemical Properties :(a) Combustion (Complete and Incomplete) - The flame is smokier than the corresponding alkanes. - The percentage by mass of carbon in alkenes is always the same, 85.71%. (b) Hydrogenation [Nickel or platinum + 180C] - Used in the manufacture of margarine (solid) from natural vegetable oil (liquid). C3H6 + H2 C3H8 Propene + Hydrogen Propane (c) Halogenation [No catalyst and no ultraviolet light] - As a chemical test to identify unsaturated hydrocarbon (double bond) as saturated organic compound do not decolourise liquid halogen but unsaturated organic compound will. C3H6 + Br2 C3H6Br2 Propene + Bromine 1,2 - dibromopropane (d) Addition of Hydrogen Halide - To produce chloro-alkane, bromo-alkane and iodo-alkane C3H6 + HCl C3H7Cl Propene + Hydrogen Chloride Chloropropane (e) Hydration [Phosphoric acid + 300C + 60 atm] - Alkanes do not react with cold water under ordinary conditions. C3H6 + H2O C3H7OH Propene + Water Propan-1-ol (f) Addition of Hydroxyl Groups [Diluted acidified potassium manganate (VII) solution] - Diluted acidified potassium manganate (VII) solution (Mixture of potassium manganate (VII) solution and dilute sulphuric acid strong acid) - Purple colour of potassium manganate (VII) solution is decolourised and a colourless organic compound called a diol is formed.

- As a chemical test to identify unsaturated hydrocarbon (double bond) as saturated organic compound do not decolourise the purple solution of potassium manganate (VII) solution but unsaturated organic compound will. C3H6 + [O] + H2O C3H7(OH)2 Propene + [O] + Water Propan-1,2-diol (g) Polymerisation [200C + 1200 atm] H H H H | | | | n C=C --- C - C ------| | | | H | H | H - C-H H - C-H n | | H H Propene Polypropene Alcohol (C2H2n+1OH, n = 1, 2, 3 ) Hydroxyl group (functional group) determines the chemical properties as it take parts in the chemical reaction. There is not hydroxide ions, OH in alcohol, thus, alcohol does not show any alkali properties. For alkene molecules containing three or more carbon atoms, the position of the double bond must be specified. Chemical Properties :(a) Combustion (Complete and Incomplete) - Alcohols are very flammable substances and burns with a non-smoky blue flame in complete combustion. - Combustion of alcohol gives out a lot of heat energy, making alcohol as a good fuel. - Alcohol is a clean fuel because it does not release pollutants into the atmosphere. (b) Oxidation - Oxidising agent is needed. Acidified Potassium Manganate (VII) Solution / Acidified Potassium Dichromate (VI) Solution C3H7OH + 2[O] C2H5COOH + H2O Propanol + Acidified Potassium Manganate (VII) Solution Propanoic Acid + Water (c) Dehydration - Alcohol vapour is passed over a heated catalyst (Porcelain chips / Porous pot / Aluminium Oxide) - Alcohol is heated under reflux + 170C + Excess Concentrated Sulphuric Acid C3H7OH C3H6 + H2O Propanol Propene + Water Uses of alcohol :- As a fuel clean fuel, bio fuel, gasohol - As a solvent perfumes, cosmetics, toiletries - As a thinner lacquer, varnish, shellac, ink - As a cleaner compact disc, video cassette, recorder head - As a raw material in the manufacturer of vinegar, plastics and explosives. - As a raw material to make pharmaceutical products tincture, antiseptic, cough syrup and rubbing alcohol. - In making alcoholic drinks beers, wines, spirits Carboxylic Acid (CnH2n+1COOH, n = 0, 1, 2 ) Colourless liquid with vinegar smell and turns blue litmus paper to red. Carboxyl group (functional group) determines the chemical properties as it take parts in the chemical reaction. It consists of a carbon atom which forms a double bond with an oxygen atom and a single bond with the hydroxyl group. Chemical Properties :-

Carboxylic acid is a weak monoprotic because it undergoes partial ionisation in water with low + concentration of hydrogen ions, H . Thus, it has similar chemical properties with WEAK acid. (a) Esterification [Concentrated Sulphuric Acid] - This reaction is only for carboxylic acid. - Concentrated sulphuric acid acts as catalyst to speed up the esterification reaction and also acts as drying agent absorbs water to produce more ester. + - Water is formed from the reaction between the HYDROGEN ions, H from carboxylic acid and HYDROXIDE ions, OH from alcohol. C3H7OH + C2H5COOH C2H5COOC3H7 + H2O Propanol + Propanoic Acid Propyl Propanoate + Water Uses of carboxylic acid :- Methanoic acid to coagulate latex - Ethanoic acid preservative and flavouring in food - Benzoic acid preservative in food (as perfumes)

Ester CnH2n+1COOCmH2m+1, n = 0, 1, 2 and m = 1, 2, 3 ) Colourless liquid with a sweet smell (fruits or flowers). Uses of carboxylic acid :- To make perfumes, cosmetics and food flavourings. - As a solvent for many organic compound (sunburn lotion) - Production of soaps and detergents. - To make synthetic polymer (polyester) which is used as synthetic fibres for making clothing fabrics. Preparation of Alcohol

PICTURE
a) Hydration in petroleum fractions (industry) b) Fermentation between sugar and starch Anaerobic in which means it take place in the absence of oxygen Yeast releases biological enzyme called zymase and the zymase will slowly decompose the glucose to form ethanol and carbon dioxide. Preparation of Carboxylic Acid

PICTURE
The flask is fitted with an upright condenser to prevent the loss of a volatile liquid by vaporisation. (Condense alcohol vapour to liquid alcohol and then flow back to the flask) Method of retaining a volatile liquid during heating is called refluxing and it is used to ensure that the reaction foes to completion (100%). Preparation of Ester

PICTURE
Can be prepared by fractional distillation (esterification). A mixture of glacial carboxylic acid with absolute alcohol (PURE but not AQUEOUS SOLUTION).

Comparison of Alkanes and Alkenes Hydrocarbon Colour Physical State Alkanes Number of carbon 1 4 : Gases 5 17 : Liquid > 17 : Solid Melting and Boiling Point Alkenes All are colourless Number of carbon 2 4 : Gases 5 15 : Liquid > 15 : Solid Low

Attractive force between the molecules is weak Van der Waals force. Thus, only a little amount of heat energy is required to overcome the weak Van der Waals force of attraction. Increase when going down the group

Density

Solubility (Water) Solubility (Organic Solvent [Benzene]) Electrical Conductivity Reaction with Oxygen [Combustion] Reaction with Bromine [Halogenation] Reaction with Acidified Potassium Manganate (VII) Solution

Number of carbon atoms in the molecule increase. Thus, the molecular size of increases and the weak Van der Waals force of attraction between the molecules become stronger. Thus, more energy is required to overcome the strong Van der Waals force of attraction when going down the group. Low [Less dense than water] Increase when going down the group The relative molecular mass of the molecule increase and molecules are packed more closely together. Insoluble Soluble Cannot conduct Do not contain free mobile ions. Burns with a sooty yellow flame. Brown colour of liquid bromine remains unchanged in alkanes. Purple colour of liquid bromine remains unchanged in alkanes. Burns with a more sooty yellow flame. Brown colour of liquid bromine is decolourised in alkenes. Purple colour of liquid bromine is decolourised in alkenes.

Homologous Series [Family] Characteristics ;1. Members can be represented by a general formula. 2. Molecular formula of members differ from other by a CH2 group [relative molecular mass of 14] 3. Members can be prepared by similar method. 4. Physical properties of members change regularly with increasing number of carbon atoms. [Melting and boiling points, Physical State, Density] 5. Chemical properties of members are similar as they have the same functional group.

Isomerism Isomers have different physical properties BECAUSE they have different structural formula. Isomers have same chemical properties BECAUSE they have same functional group or belong to same homologous series. | | -C-C| | | | | | | | | -C-C-C- C - C -C-C- C-C-C-C| | | | | | | | | -C-C| | Branched Straight Chain Chain Naming of isomers - Name the longest and straight carbon chain. - Name the carbon atoms in this longest chain. - Locate and name the attached alkyl group. [Position = Number of Carbon atom that is attached] Organic Compounds Reasons of Isomerism Conditions of Longest Chain Ways to name the carbon atoms MethEthPropButPentAlkanes Different carbon chains From the nearest alkyl group 0 0 0 2 3 in Alkenes Different in carbon chains Position of double bond Contain double bond From the nearest double bond 0 0 3 5 Alcohol Different in carbon chains Position of hydroxyl group Contain hydroxyl group From the nearest hydroxyl group 0 0 2 4 -

Number of Isomers

Comparison Between Fats and Oils Substances Sources Physical State [at room temperature] 2. 3. 4. 5. Fats [Butter] Animal Solid Sources of energy Sources of nutrients Thermal insulation Protection and structural role Oils [Palm Oil] Plant Liquid

Uses

Each fat molecule contains 3 fatty acid molecules and 1 glycerol molecule :- Fatty acid (is not called carboxylic acid because it is too long) is a carboxylic acid that contains 12 to 18 carbon atoms per molecule - Glycerol is an alcohol that contains 3 hydroxyl group per molecule Propane-1,2,3-triol. Molecular structural of a molecule of fat

PICTURE
Saturated and Unsaturated Fats The fatty acids can be differentiated in two main ways :a. The length of the carbon chain from 12 to 18 carbon atoms b. The fatty acid may be saturated or unsaturated * A saturated fatty acid has all carbon-carbon single bond. Eg. Palmitic acid, stearic acid. * A unsaturated fatty acid has one or more carbon-carbon double bond. Monounsaturated fatty acid : One carbon-carbon double bond [Oleic Acid] Polyunsaturated fatty acid : Two or more carbon-carbon double bond [Lenoleic Acid] Fats Similarities Type of Fatty Acids Type of Bond Differences Melting Point Sources Physical State Cholesterol Content Saturated Fats Unsaturated Fats A mixture of different ester formed from a variety of long-chain carboxylic acid called fatty acid with the alcohol called glycerol. Saturated Carbon-carbon Single Bond High Animal Solid High Unsaturated Carbon-carbon Double Bond Low Plant Liquid Low

Converting Unsaturated Fats to Saturated Fats (Hydrogenation) Bubbling hydrogen gas through hot (180C - 200C) and liquid oil in the presence of nickel or platinum as catalyst. As more and more of the double bond get hydrogenated, the relative molecular mass of the oil molecule increases. Intermolecular force becomes stronger and more energy is needed to overcome them. The boiling point of the oil increases and the physical state change from liquid to solid. The hardness of fats produced by hydrogenation depends on the quantity of hydrogen absorbed. The greater the amount of hydrogen absorbed, the harder the solid fats produced.

Natural Rubber Obtained from the latex secreted by rubber tree. Isoprene (2-methylbuta-1,3-diene) ---(Addition Polymerisation) Polyisoprene (Natural Rubber) H H H H H H | | | | | | n H - C = C - C = C - H ---- C - C = C - C ----| | | | H - C- H H | H | H - C- H H | n H Isoprene Polyisoprene (2-methybuta-1,3-diene) Natural Rubber has one double bond per repeating unit while isoprene has two double bonds.

Coagulation of Latex Latex is a colloid (in liquid state but sticky) which consists of rubber particles dispersed in water. Each rubber particle is made up of many long chains rubber molecule covered with a membrane of protein which is negatively-charged. The repulsion between the negatively-charged particles prevents the rubber particles from coming close to each other. Hence, latex could not coagulate and remain in liquid state.

PICTURE
a. ACID (Methanoic acid) + - When an acid is added, the hydrogen ions, H neutralise the negative charged on the protein membrane. The particles can now close together, enabling them to collide with one another resulting in the breakage of the protein membrane. The rubber molecules combine with one another and thus causing the latex to coagulate. b. ALKALI (Ammonia solution) - When an alkali is added, the latex can be preserved in the liquid state. It contains hydroxide ions, OH- that neutralise the acid produced by the bacteria. Hence, the rubber particles remain negatively-charged and the coagulation is prevented. c. NONE - When it is exposed to air, the growth and spread of bacteria from the air will produce lactic acid that causes the coagulation of latex. Due to the slow bacteria action, the coagulation of latex takes a longer time to occur.

Vulcanization of Rubber This process is carried out by a) Heating natural rubber with sulphur using zinc oxide as catalyst. b) Immerse natural rubber in the solution of disulphur dichloride, S2Cl2 in methylbenzene. In vulcanization of rubber, the sulphur atoms are added to the double bond in the natural rubber molecules to form sulphur cross-links between the rubber particles. When vulcanized rubber is stretched and released, the cross-linkages pull the chains back to their original arrangement, improving the elasticity and strength of the rubber. The presence of sulphur-linkages increases the size of rubber molecules. Therefore, the melting point of rubber increases, causing vulcanized rubber more resistant to heat and organic solvent Vulcanized rubber has much less carbon-carbon double bond as compared to unvulcanized rubber. This explains the higher resistant of vulcanized rubber to oxidation.

PICTURE
The greater the amount of sulphur added, the stronger and harder and more difficult to stretch, but more elastic (ability to return to its original shape). Vulcanized Rubber High Hard Strong Can withstand high temperature Hard to oxidised Types of Rubber Elasticity Hardness Tensile Strength Resistant to Heat Resistant to Oxidation Unvulcanized Rubber Low Soft Weak Cannot withstand high temperature Easy to oxidised

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