Alcohol ChemistryAlcohol ChemistryUses:Uses: Alcoholic drinks (ethanol)Alcoholic drinks (ethanol) SolventsSolvents FuelsFuels

IntroductionIntroduction Are a family of organic compounds Are a family of organic compounds

containing the containing the –OH (hydroxyl)–OH (hydroxyl) functional groupfunctional group

Draw the FSF and write molecular formulae for:1. Methanol2. 2-methylpropan-1-ol3. 2-methylbutan-2-ol

Naming practiceNaming practice

CH

H

H

C C C CH H

HH

HH H

H

HCH

H

C

HC

CH HH

HO

C

H

HH

heptan - - ol43 - ethyl, 4 - methyl

A homologous seriesA homologous series A family of compounds with the A family of compounds with the same same

general formulageneral formula, , similar chemical similar chemical propertiesproperties and a and a graduation in physical graduation in physical propertiesproperties

ALCOHOL:Any compoundcontaining the

-OH group

ALKanols:Subset based on alkanes

AlcoholAlcohol The chemical name for alcohol is The chemical name for alcohol is

ETHANOLETHANOL:: Ethanol is NOT a carbohydrate.Ethanol is NOT a carbohydrate. Alcoholic drinks are made by Alcoholic drinks are made by

fermenting sugar (glucose)fermenting sugar (glucose)::

C

C

H

H

H

H

H

OH

DrinkDrink CarbohydratCarbohydratee % alcohol% alcohol

BeerBeer BarleyBarley 3 - 63 - 6CiderCider ApplesApples 7 – 107 – 10WineWine GrapesGrapes 10 – 1410 – 14WhiskyWhisky BarleyBarley 35 – 4535 – 45VodkaVodka PotatoesPotatoes 35 - 4535 - 45

FermentationFermentation Alcohol is made from sugarAlcohol is made from sugar The process is called The process is called FERMENTATIONFERMENTATION::

An An ENZYMEENZYME is needed to make this is needed to make this

reaction happen - reaction happen - ZymaseZymase YEASTYEAST (a living organism) contains the (a living organism) contains the

enzyme which is needed enzyme which is needed

Glucose Alcohol + Carbon dioxide

Making EthanolMaking Ethanol

(C6H10O5)n

starchEnzyme maltase in yeast

C6H12O6

glucose

Enzyme zymase in yeast C2H5OH + CO2

ethanol

C12H22O11

maltose

Enzymes released during germination

FERMENTATION

PracticalPractical Burning £5 noteBurning £5 note

Practical demoPractical demo Alcohol RocketAlcohol Rocket

Collect a copy of “That’s the Limit” booklet

That’s the Limit 1That’s the Limit 1 How much How much beerbeer contains the equivalent alcohol to contains the equivalent alcohol to

oneone glass of wineglass of wine?? How much How much beerbeer contains the equivalent alcohol to contains the equivalent alcohol to

a a single whiskeysingle whiskey?? Pint for pint, which contains more alcohol, Pint for pint, which contains more alcohol, beerbeer or or

cidercider?? What are the What are the recommended weekly unitsrecommended weekly units of drink of drink

for men and women?for men and women? Which Which organ organ is chiefly responsible for removing is chiefly responsible for removing

alcohol from the body?alcohol from the body? List List 3 factors3 factors which affect how you are affected by which affect how you are affected by

alcohol.alcohol.

That’s the Limit 2That’s the Limit 2 How long would it take your body to remove the alcohol How long would it take your body to remove the alcohol

consumed by consumed by 4 pints of beer4 pints of beer?? What is the What is the legal driving limitlegal driving limit in terms of units of in terms of units of

alcohol?alcohol? If you started drinking at 8pm, and consumed on If you started drinking at 8pm, and consumed on

average 2 pints every hour until 12pm, how long would average 2 pints every hour until 12pm, how long would it take you to be below the legal limit for driving?it take you to be below the legal limit for driving?

Explain what causes a Explain what causes a hang-overhang-over.. State State 3 long-term effects3 long-term effects of excessive alcohol of excessive alcohol

consumption.consumption.

Alcoholic DrinksAlcoholic Drinks

DrinkDrink CarbohydrateCarbohydrate % alcohol% alcoholBeerBeer BarleyBarley 3 - 63 - 6CiderCider ApplesApples 7 – 107 – 10WineWine GrapesGrapes 10 – 1410 – 14WhiskyWhisky BarleyBarley 35 – 4535 – 45VodkaVodka PotatoesPotatoes 35 - 4535 - 45

•At alcohol concentrations above 15 %, the yeast are poisoned and the enzymes do not work.

•Fermentation therefore stops.

DistillationDistillation

To produce drinks To produce drinks with a high alcohol with a high alcohol concentration, concentration, DISTILLATIONDISTILLATION must must be carried out.be carried out.

cold water in

cold water out

mixture fromfermentation

'anti-bumping' glass beads

distilledethanol

Alternative method?Alternative method? Fermentation is too expensive to Fermentation is too expensive to

produce ethanol on an industrial scaleproduce ethanol on an industrial scale Catalytic hydration of etheneCatalytic hydration of ethene is is

method usedmethod usedEthene + water Ethanol

H3PO4 catalyst

300oC & 70 atmospheresC2H4 + H2O

C2H5OHC

C

H

H

H

H+

H

OH

C

C

H

H

H

H

H

OH

The reverse processThe reverse process

mineral woolsoaked in ethanol aluminium oxide catalyst

rolled in mineral wool

ethene

This is called DEHYDRATION

Chemistry of Chemistry of dehydrationdehydration

water

+

Ethanol Ethene

C C C COH

HH

HHH

HHH

H+ O

H H

C C C C H

HHH

HHH

HNAME?

C C C C H

HHH

HHH

HNAME?

PracticePractice Draw the FSF for the product(s) of Draw the FSF for the product(s) of hydrationhydration

of the following alkenes:of the following alkenes: 3-methylpent-1-ene3-methylpent-1-ene 2-methylbut-1-ene2-methylbut-1-ene 2-methylbut-2-ene2-methylbut-2-ene

Which of the following compounds will Which of the following compounds will produce isomers on produce isomers on dehydrationdehydration??

Hexan-3-olHexan-3-ol Heptan-3-olHeptan-3-ol 2-methylbutan-1-ol2-methylbutan-1-ol