Soap

Soap = sodium salts (RCOO-Na+) / potassium salts (RCOO-K+) of longchain fatty acids Alkalis react with fatty acids > soap Fatty acids = animal fats or vegetable oils Soap preparation: hydrolysing fats or oils under alkaline condition Saponification alkaline hydrolysis Saponification process boiling fats / oils with concentrated sodium hydroxide solution or concentrated potassium hydroxide solution to produce glycerol + salts of fatty acids (soap)

Saponification steps: 1. Hydrolysis of fats / oils > glycerol + fatty acids. 2. Neutralisation of fatty acids + concentrated alkali > soap + water Overall equation: Fats / oils + alkali > glycerol + soap Sodium chloride reduces the solubility of soap in water Solid soap + unsaturated oil (sunflower oil / olive oil) Uses: shaving cream

Liquid soap saturated oils (coconut oil) Uses: bathing purposes

Sodium hydroxide + Potassium hydroxide

Detergent

Detergent = sodium salt of sulphonic acid Alkalis react with sulphonic acid > detergent Common detergent: sodium alkyl sulphate & sodium alkylbenzene sulphonate. Detergent preparation: 2 processes 1. Sulphonation. 2. Neutralisation. Sulphonation: Petroleum fraction (long chain hydrocarbon compounds) converted into sulphonic acid with the present of concentration sulphuric acid. Water molecule is removed.

Neutralisation: sulphonic acid neutralised with sodium hydroxide to form detergent (water molecule is formed). Other type of detergents: 1. Anionic detergent (dishwashing liquid detergent). 2. Cationic detergent (hair conditioner). 3. Non-ionic detergent (car washing detergent).

Cleansing action of soap and detergent

Soap and detergent are surfactants. Surfactants are organic compounds that lower the surface tension of a liquid. Surfactants act as emulsifiers and foaming agents. Anion soap consists of carboxylate ion (hydrophilic = soluble in water) and long hydrocarbon tail (hydrophobic = soluble in grease /oils). Anion detergent consists of sulphate ion / sulphonate ion (hydrophilic = soluable in water) and long hydrocarbon tail (hydrophobic = soluble in grease / oils).

The action process 1. Soap or detergent is added to water. 2. This has lower the surface tension of water and increases the wetting ability of water. 3. Hydrophilic part of the anion dissolves in water. 4. Hydrophobic part dissolves in grease. 5. Scrubbing helps to pull the grease free and break the grease into small droplets.

6. These droplets do not coagulate and redeposit on the surface of the cloth. It is because therepulsion between negative charges on the surface. 7. The droplets are suspended in water forming an emulsion. 8. Foam produces to float the emulsion. 9. Rinsing helps to remove these droplets. The effectiveness of the cleansing action of soap and detergent Condition Hard water (contain calcium & magnesium ion) Soap Form an insoluble precipitate = soap soap scum causes wastage of soap) Detergent Detergent is effective cleaner. substances = calcium or magnesium salts (do not form scum) Soft water (do Soap is effective not contain calcium & magnesium ion) Acidic water (contain Form insoluble long-chain fatty Detergent is effective cleaner. Form soluble form scum) Soap is nonbiodegradable Example protease Control foaming in detergent Silicones cleaner. Detergent is effective cleaner.

scum (formation of Form soluble

hydrogen ion) acids (reduces the for cleaning) Environment Soap is biodegradable Additives in detergent Additives Biological enzyme Foam control agent Function

amount of soap used substances (Do not

Remove protein stains Amylase, lipase &

Builder Filler

Enhance the surfactant Sodium phosphate efficiency Make the solid detergent dry and enable the liquid detergent to be poured easily Sodium silicate

Fragrance Optical brightener

Add fragrance Add brightness by convert UV radiation to blue light and whiteness

Fluorescent dye

Stabilising agent Suspension agent

Lower the production Silicones of foam Prevent the dirt particles removed from redepositing onto cleaned fabrics Sodium carboxymethylcellulose

Whitening agent

Bleach stains

Sodium hypochlorite

1. Comparing (Similarities and Differences) Properties of Alkanes and Alkenes Physical Properties Physical state Physical state changes Same with alkanes. from gas to liquid when going down the series. Electrical conductivity. Boiling points and melting points Do not conduct electricity at any state. Low boiling points and Same with alkanes. melting points (number of carbon atoms per molecule increases). Density Low densities (number Same with alkanes. of carbon atom per Same with alkanes. Alkanes Alkenes

molecule increases). Solubility in water Chemical Properties Reactivity Combustion Insoluble in water (soluble in organic solvent) Alkanes Alkenes (Substitution reaction) (Addition reaction) Unreactive Burn in air and produce yellow sooty flame. Reaction with bromine solution Reaction with acidified potassium manganate(VII) solution 2. Isomerism Isomerism phenomenon that two or more molecules are found to have the same molecular formula but different structural formulae. Isomerism in alkanes Molecular formula Number of isomers CH4 C2H6 C3H8 C4H10 C5H12 - (no isomer) - (no isomer) - (no isomer) 2 3 Methane Ethane Propane Butane2methylpropane Pentane2methylbutane2,2Structure name No reaction. Decolourise purple acidified potassium manganate(VII) solution. No reaction. Reactive Burn in air and produce yellow and sootier flame compare to alkanes. Decolourise brown bromine solution. Same with alkanes.

dimethylpropane Isomerism in alkenes Molecular formula Number of isomers C2H4 C3H6 C4H8 - (no isomer) - (no isomer) 3 Ethene Propene But-1-eneBut-2ene2methylpropene C5H10 5 Pent-1-enePent-2ene2-methylbut-1ene 3-methylbut-1-ene 2-methylbut-2-ene Structure name

Non-Hydrocarbon Alcohol 1. General formula: CnH2n + 1OH

Where n = 1, 2, 3 (n = number of carbon)

2. Alcohols are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms. 3. The functional group in alcohols is hydroxyl group, OH. Name of alcohol Methanol Ethanol 1-ol Butanol / Butan-1- C4H9OH ol Pentanol / Pentan- C5H11OH Molecular formula of alcohol CH3OH C2H5OH

Propanol / Propan- C3H7OH

1-ol Hexanol / Hexan-1- C6H13OH ol Heptanol / Heptan- C7H15OH 1-ol Octanol / Octan-1ol Nonanol / Nonan-1- C9H19OH ol Decanol / Decan-1- C10H21OH ol 4. Physical properties of alcohol Name Molecular Melting Boiling Physical state formula Methanol CH3OH Ethanol C2H3OH Propanol C3H5OH Butanol C4H7OH Pentanol C5H9OH

C8H17OH

point (C) -97 -117 -127 -90 -79

point (C) 65 78 97 118 138

at 25C Liquid Liquid Liquid Liquid Liquid

Solubility in water all members in alcohol are very soluble in water (miscible with water). Volatility all alcohols are highly volatile. Colour and Smell alcohols are colourless liquid and have sharp smell. Boiling and melting points all alcohols in general have low boiling points (78C).

5. Chemical properties of alcohol

Combustion of alcohol Complete combustion of alcohol. C2H5OH + 3O2 > 2CO2 + 3H2O (Alcohol burns with clean blue flames. Alcohol burns plenty of oxygen to produce carbon dioxide and water. This reaction releases a lot of heat. Therefore, it is a clean fuel as it does not pollute the air.) Other example: 2C3H7OH + 9O2 > 6CO2 + 8H2O

Oxidation of ethanol In the laboratory, two common oxidising agents are used for the oxidation of ethanol which are acidified potassium dichromate(VI) solution (orange to green) and acidified potassium manganate(VII) solution (purple to colourless). C2H5OH + 2[O] > CH3COOH + H2O Ethanol oxidised to ethanoic acid (a member of the homologous series of carboxylic acids will be discussed in Part 6). Other example: C3H7OH + 2[O] > C2H5COOH + H2O

Removal of water (Dehydration) Alcohol can change to alkene by removal of water molecules (dehydration). It results in the formation of a C=C double bond. CnH2n+1OH > CnH2n + H2O C2H5OH > C2H4 + H2O Two methods are being used to carry out a dehydration in the laboratory. a) Ethanol vapour is passed over a heated catalyst such asaluminium oxide, unglazed porcelain chips, pumice stone or porous pot. b) Ethanol is heated under reflux at 180C with excess concentrated sulphuric acid, H2SO4. Other example: C3H7OH > C3H6 + H2O

6. Uses of Alcohol

Alcohol as a solvent (cosmetics, toiletries, thinners, varnishes, perfumes). Alcohol as a fuel (fuel for racing car, clean fuel, alternative fuel). Alcohol as a source of chemicals (polymer, explosives, vinegar, fiber). Alcohol as a source of medical product (antiseptics for skin disinfection, rubbing alcohol).

7. Misuse and Abuse

Depressant drug Alcoholic drinks Addictive drug

Non-Hydrocarbon Carboxylic Acids 1. General formula: CnH2n+1COOH

Where n = 0, 1, 2, 3 (n = number of carbon)

2. Carboxylic acids are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms. 3. The functional group in alcohols is carboxyl group, COOH.

Name of carboxylic Molecular formula of acids Methanoic acid(Formic acid) Ethanoic acid(Acetic acid) Propanoic acid Butanoic acid Name Methanoic acid(Formic acid) Ethanoic acid(Acetic acid) Propanoic acid Butanoic acid C3H7COH

alcohol HCOOH CH3COOH C2H5COOH C3H7COH Molecularformula Boiling point (C) HCOOH 101

4. Physical properties of carboxylic acid

CH3COOH

118

C2H5COOH

141 164

Solubility in water generally in carboxylic acid (the less than four carbon atoms) arevery soluble in water and ionise partially to form weak . Density of carboxylic acid density of carboxylic acid increases due to the increases in the number of carbon atoms in a molecule. Boiling points all carboxylic acid in general have relatively high boiling points than the corresponding alkanes. This is due to the presence of carboxyl group in carboxylic acid.

Smell carboxylic acid (< 10 carbon) are colourless and pungent smell. Carboxylic acid (>10 carbons) are wax-like solids.

5. Preparation of carboxylic acid

Oxidation of an alcohol The oxidation of ethanol is used to prepare ethanoic acid. C2H5OH + 2[O] > CH3COOH + H2O

Carried out by refluxing* ethanol with an oxidising agent [acidified potassium dichromate(VI) solution orange colour turns to green / acidified potassium manganate(VII) solution purple colour turns to colourless] * reflux = upright Liebig condense to prevent the loss of a volatile liquid by vaporisation. 6. Chemical properties of carboxylic acid

Acid properties Ethanoic acid is a weak monoprotic acid that ionises partially in water (produce a low concentration of hydrogen ions). CH3COOH <> CH3COO- + H+ Ethanoic acid turns moist blue litmus paper red.

Reaction with metals Ethanoic acid reacts with reactive metals (copper and metals below it in the reactivity series cannot react with ethanoic acid). (K, Na, Mg, Al, Zn, Fe, Sn, Pb, Cu, Hg, Au) 2CH3COOH + Zn > Zn(CH3COO)2 + H2 In this reaction, a colourless solution (zinc ethanoate) is formed. 2CH3COOH + Mg > Mg(CH3COO)2 + H2 In this reaction, a colourless solution (magnesium ethanoate) is formed.

Reaction with bases acid neutralises alkalis (sodium hydroxide). CH3COOH + NaOH > CH3COONa + H2O In this reaction, a salt (sodium ethanoate) and water are formed.

Reaction with carbonates Ethanoic acid reacts with metal carbonates (calcium carbonate, magnesium carbonate, zinc carbonate). 2CH3COOH + CaCO3 > Ca(CH3COO)2 + CO2 + H2O In this reaction, a salt (calcium ethanoate), carbon dioxide and water are formed.

Reaction with alcohols (Esterification) Ethanoic acid reacts with alcohol (ethanol, propanol, butanol) CH3CO-OH + H-OC4H9 > CH3COOC4H9 + H2O (Concentrated H2SO4 is a

catalyst) In this reaction, an ester (colourless sweet-smelling liquid) (butyl ethanoate) and water are formed. 7. Uses of Carboxylic Acid

Carboxylic acid (methanoic acid and ethanoic acid) is used to coagulate latex. Vinegar (dilute 4% of ethanoic acid) is used as preservative and flavouring. Ethanoic acid is used to make polyvinvyl acetate which is used to make plastics and emulsion paints. Benzoic acid is used as food preservative. Butanoic acid is used to produce ester (artificial flavouring).

Polymers 1. Polymer many small units (monomers) joining together to formed large molecule. 2. Polymer can be classified into two groups:

synthetic polymers / man-made polymers (polythene; PVC polyvinyl chloride; artificial silk; and polypropene) natural polymers (natural rubber; starch; cellulose; and proteins)

3. Natural polymer: Carbohydrates (polysaccharides) (starch, glycogen and cellulose)

General formula: Cx(H2O)y with the ratio of H:O = 2:1 Carbohydrates have cyclic structure. Monomer: glucose (C6H12H6) Reaction to form polymer: condensation reaction (- H2O) Protein consists of carbon, hydrogen, oxygen and nitrogen (some have sulphur, phosphorus and other elements) Monomer: amino acids Amino acids have two functional group which are carboxyl group (-COOH) and amino group(-NH2) Reaction to form polymer: condensation reaction (- H2O) Extracted from the latex of rubber tree (Hevea brasiliensis) which the tree originates from Brazil. A molecule of rubber contains 5000 isoprene units. Monomer: isoprene, C3H8 or 2-methylbuta-1,3-diene. Reaction to form polymer: additional polymerisation (one of the double bond in isoprene becomes single bond)

4. Natural polymer: Protein (polypeptide)

5. Natural polymer: Natural rubber

6. Structure of rubber molecule

Latex is colloid (35% rubber particles and 65% water). Rubber particle contains rubber molecules which are wrapped by a layer of negatively-charged protein membrane. Same charge of rubber molecules repels each other. This prevent rubber from coagulate.

7. Coagulation process of latex

The process for the coagulation of latex is summarised as: 1. Acid (H+) can neutralise the negatively-charged protein membrane. Example of acid: formic acid, methanoic acid, suphuric acid and hydrochloric acid. 2. The rubber molecules will collide after the protein membrane is broken. 3. Rubber molecules (polymers) are set free 4. Rubber molecules combine with one another (coagulation). 8. Natural coagulation process of latex For the natural coagulation of latex: 1. Latex is exposed to air without adding acid (duration overnight). 2. Coagulation process occurs in slower pace due to the bacteria (microorganism) action which produce acid) 9. Prevent coagulation process of latex The following are latex coagulation prevention method: 1. Alkaline / Basic solution is added to the latex. Example: ammonia (NH3). 2. Positively-charged hydrogen ion / H+ produced by bacteria can be neutralised by negatively-charged hydroxide ion / OH- from ammonia solution. 10. Properties of natural rubber

elastic cannot withstand heat (become sticky and soft above 50C; decompose above 200C; hard and brittle cooled) easily oxidised (present of C=C) insoluble in water (due to the long hydrocarbon chains) soluble in organic solvent (propanone, benzene, petrol etc.)

11. Vulcanisation of rubber Vulcanisation process of hardening rubber and increases rubber elasticity by heating it withsulphur or sulphur compounds. Methods:

heating natural rubber with sulphur at 140C using zinc oxide as catalyst or

dipping natural rubber in a solution of disulphur dichloride (S2Cl2) in methylbenzene.

12. Properties of vulcanisation of rubber

The sulphur atoms are added to double bonds in the natural rubber molecules to formdisulphide linkages (-C-S-S-C-) / sulphur crosslinks between the long polymer chains. Therefore, vulcanised rubber is more elastics and stronger.

This increases the molecular size and the intermolecular forces of attraction between rubber molecules. Therefore, vulcanised rubber is more resistant to heat (does not become soft and sticky when hot).

This also reduces the number of carbon-carbon double bonds in rubber molecules. Therefore, vulcanised rubber is more resistant to oxygen, ozone, sunlight and other chemicals.

13. Comparison between the properties of vulcanised rubber and unvulcanised rubber Properties Double bonds Melting point Elasticity Vulcanised rubber sulphur cross-links) High (presence of sulphur) More elastic (sulphur cross-links prevents the polymer chain or rubber from slipping past. Strength and Strong and hard hardness (depends on degree of vulcanisation) Weak and soft (polymer chain of rubber will break when rubber is over stretched. Resistant to Resistant to heat heat Oxidation Resistant to oxidation Easily oxidised by (reduction of number of oxygen, UV light Poor resistant to heat Less elastics Unvulcanised rubber double bonds Low Decreases (formation of More number of

double bonds per rubber (presence of many molecule) 14. R & D of rubber

double bonds per rubber molecules)

RRIM Rubber Research Institute of Malaysia MRB Malaysian Rubber Board Rubber Technology Centre Various local higher institutions of learning

Food Additives Food additive = a natural / synthetic substance that is added to food to

prevent spoilage extend food storage life improve food appearance improve food taste improve food texture

A. Preservatives Function:

slow down / prevent the growth of microorganisms / bacteria / fungi extend food storage life

Example: Preservatives Functions Salt of the cells of microorganisms. Retards the growth of microorganisms. Sugar Draws the water out Fruit jam of the cells of microorganisms. Tooth decay, diabetes and obesity Example Side effect Increase the cardiovascular diseases vegetables risk of

Draws the water out Salted

Retards the growth of microorganisms. Vinegar Inhibits the growth of microorganisms. Sodium nitrite Slows down the / sodium nitrate growth of microorganisms. Stabilise red colour in meats. Benzoic acid / Slows down the sodium benzoate Sulphur dioxide growth of microorganisms. Slows down the growth of microorganisms. Alternative ways: freezing and refrigeration Food Additives B. Antioxidant Function:

Pickled cucumber Sausage Carcinogenic

Tomato sauce Grape juice Asthma and allergies

prevent oxidation (causes rancid fats and brown fruits)

Examples: Antioxidant Vitamin E Functions Prevent oils from turns rancid Vitamin C Preserve the colour formation of nitrosamines Sodium citrate Stop rancidity in fats Ice-cream Example Side effect Palm oil & No sunflower oil Fruit juice No meat of fruit juice and the & cured

BHA (Butylated Retard rancidity in hydroxyanisole) fats, oils and oilBHT (Butylated containing foods hydroxytoluene)

Margarine Carcinogenic & cereal