ALCOHOL

The Alcohol Family 1. One of member of homologous series which contain carbon, hydrogen and oxygen. 2. General formula for alcohol is CnH2n+1OH. [n=1,2,3..] 3. Alcohol contains the hydroxyl group, -OH as their functional group. [notes: not hydroxide ion, OH- , alcohol not is alkaly ] 4. Alcohol is neutral compound. 5. Alcohol are named by replacing -e for alkane with ol.

6. Structural formula and molecule for few alcohol. n Name Mr Molekul Formula Structural formula H | H C OH | H

12+3+ CH3OH 1 Methanol 16+1 @ = 32 CH4O

H H 12x2 + | | Ethanol C2H5OH 5 +16 H C C OH 2 very @ +1= | | important C2H6O 46 H H H H H | | | H C C C OH C3H7OH | | | H H H C4H9OH C5H11OH

Propan-1ol

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4 5

Butan-1ol Pentan-1ol Hexan-1ol

74 88

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C6H13OH

Q: Give names for this alcohol. OH CH3 CH2 CH CH2 CH2 CH3 Formula: C6H13OH Name : HEXAN-3-OL

Naming Alcohol 1. Find the longest continous carbon chain containing OH. 2. Number the carbon beginning at the end nearer to the OH, write the number in front of the ending ol. 3. Locate the alkyl group (branch chain), give number to the carbon and named the alkyl group. Put the number in front of the group. CH3 : methyl C2H5 atau CH2CH3 : ethyl C3H7 atau CH2CH2CH3 : propyl 4. Complete the name for the alcohol (ii) OH CH3 CH2 C CH2 CH2 CH3 | CH3 Formula: C7H15OH Name : 3-methyl hexan-3-ol

(iii) OH CH3 CH2 CH CH CH2 CH3 | CH3 Formula : C7H15OH Name : 4-methyl hexan-3-ol

(iii) OH CH3 CH CH CH CH2 CH2 | | | CH3 CH3 CH3 Formula : C9H19OH Name : 2, 4 dimethyl heptan-3-ol

(iv) C 2H 5 OH CH3 CH2 CH CH2 CH CH2 CH3 Formula : C9H19OH Name : 5-ethyl heptan-3-ol Physical Properties 1. Liquid at room temperature. (pg. 62) [ no gas] 2. Simple alcohol are very soluble in water, infinite solubility. Methanol, ethanol dan propan-1-ol is miscible in all proportions (terlarut campur dengan air dalam semua kadaran). The rest of the alcohol less soluble or insoluble. Isomerism Similar to alkenes, isomerism in alcohol results from the branching of the carbon chain and the different location of the hydroxyl group. You only have to know the isomerism in propanol dan butanol. Q : Draw 2 isomers for propanol and 4 isomers for butanol, and dan named the isomers.

Propanol

Butanol

Propanol

H H H H C C C OH H H H

Molecular formula: C3H7OH Name: Propan-1-ol

H H H HCCCH H OH H

Molecular formula: C3H7OH Name: Propan-2-ol

Butanol

H H H H H C C C C OH H H H H H H H H HCCCCH H H OH H

Molecular formula: C4H9OH Name: Butan-1-ol

Molecular formula: C4H9OH Name: Butan-2-ol

H H H H C C C OH H HCH H H

Molecular formula: C4H9OH Name: 2-methylpropan-1-ol

H OH H H C C C H H HCH H H

Molecular formula: C4H9OH Name: 2-methylpropan-2-ol

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ETHANOL 1. Preparation of ethanol. i. Laboratory preparation (fermentation) ii. Industrial production (hydration process) Making Ethanol Fermentation 1. Two stages; i. Fermentation ii. Purification - through fractional distillation at 78 oC ( boiling point of ETHANOL) Fermentation of Glucose 1. Yeast is added to sugar or starch. 2. Anaerobic process ( takes place in the absence of oxygen). 3. Yeast releases enzymes. These enzymes break down the sugars/starch into glucose, C6H12O6. 4. Zymase slowly decomposes the glucose to form ethanol and carbon dioxide. Zymase @ C2H5OH @ C2H6O 2CH3CH2OH (l) + 2CO2 (g) o 30 C

C6H12O6 (aq)

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Delivery tube Conical flask Beaker Glucose + yeast Lime water

When the concentration of ethanol reach 15%, the yeast dies. Q: How to produce pure alcohol? A: Purified the ethanol through fractional distillation. Purification of Ethanol 1. Ethanol produced from the fermentation process is impure, because its mix with the glucose solution. Q : Draw labeled diagram to carry out the purification of ethanol through fractional distillation process.

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 Thermometer Water out Liebig condenser Retort stand with clamp Water Product from fermentation Wire gauge Rounded conical Porcelain chips Bunsen burner Water in Distillate (Ethanol)

Fractioning collum

XXXXXXXXXXXXXXX

Q: Why the solution/filtrate in rounded conical must heated at 78oC. A: The boiling point of ethanol is 78 oC. Q: Ethanol produced may still contains of some water. What should be done to be sure that ethanol is 100% pure? A: Anhydrous calcium oxide or anhydrous calcium chloride is add/put into the ethanol.

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Q: What is the function of; - thermometer - porcelain chips - Liebig condenser A: thermometer is used to ensure that temperature is always at 78 oC. B: Porcelain chips is used to avoid the solution jumped/ effervesence (breaking bubbles) C: To cooled the ethanol vapour to become liquid. Q: Named the process in Liebig condenser. A: Condensation Q: What is the properties of ethanol A: Properties; - colourless - volatile - good organic solvent - miscible with water - highly flammable - antiseptic - chemically reactive

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Q: What is the uses of ethanol A: Uses; As a solvent in perfumes/cosmetics As a thinner in varnish, ink As a cleaner for compact disc. As a fuel for transport As a raw material for the manufacture of vinegar, As a raw material to make industrial product such as antiseptic and cough syrup.

Industrial production of ethanol Ethene is mix with steam is passed through concentrated phosphoric acid (catalyst) at 300 oC (temperature) and 60 atmosphere (pressure). H3PO4 concentrsted H2O 300 o C, 60 atm

@ C2H4 CH2 = CH2 +

C2H5OH CH3CH2OH

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Chemical Properties 1. Combustion i. Alcohol are very flammable sustances. ii. Ethanol burns with non-smoky and blue flame and releases lot of heat. Suitable for use as fuel, described as clean fuel.

C2H5OH Ethanol

3O2 Oxygen

2CO2 + Carbon dioxide

3H2O Water

Q: Write combustion equation for hexanol C6H13OH hexanol + 9O2 Oxygen 6CO2 + Carbon dioxide 7H2O Water

2. Oxidation i. Ethanol can be oxidised into ethanoic acid by an oxidising agent. [Ethanoic acid is a family of carboxilic acids]

CH3CH2OH Etanol

2[O]

CH3COOH + H2O Ethanoic acid

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Q: Show the structural formula for the equation above.

H H | | H C C OH + 2[O] | | H H

H O | H C C OH + H2O | H

Q: Named 2 solutions are commonly used as oxidising agent. (i) (ii) Acidified potassium manganate(VII), KMnO4 (purple to colourless / decolourised) Acidified potassium dichromate(VI), K2Cr2O7 (orange to green)

Q: Draw a labeled diagram for the process.

Ethanol + potassium dikromat(VI) + dilute sulfuric acid

Heat Distillate (ethanoic acid) Cold water

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Distillate (ethanoic acid) - Colourless - Vinegar smell - Blue litmus paper turns red (acidic properties) 3. Dehydration

- H2O

ALCOHOL

ALKENE

1. Converted ethanol into ethene and a molecule of water. 2. The elimination of water results the formation of a carbon-carbon double bond. 3. Dehydration occur when a. ethanol vapours is passed over a heated catalyst such as. i- Porous pot / porcelain chips ii- Purnice stone / aluminium oxide, Al2O3 /alumina b. Ethanol is heated under reflux at 170 oC with excess concentrated sulphuric acid.

CH3CH2OH Ethanol

CH2 = CH2 Ethene

H2O

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Q : Draw the structural molecule for the process H H | | HCCH | | H OH H H | | H C C H + H 2O

Q : Draw labeled diagram.

Glass wool soaked with ethanol

Porcelain chips Ethene gas Delivery tube Test tube Retort stand with clamp

Heat

Heat

Water

Prepared by; Kamal Ariffin Bin Saaim SMKDBL http://kemhawk.webs.com

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