Alcohols

- Organic compounds with functional hydroxyl group = OH

- General formula CnH2n+1OH… or… CnH2n+2O
- Suffix… -ol, Prefix… hydroxy-
- Are solvents (for things that are not soluble in water)
- USES: For drinking (ethanol), NOT for drinking (methanol), disinfection, burning them

Mix with water because of HYDROGEN BONDING (alkanes do not = hydrophobic)

o Shorter molecules mix better, because when the hydrophilic part of looong alcohol (OH) mixes with
water we are left with alkane – hydrophobic (WAX for skis)
o They are polar molecules -O is slightly negative -H is slightly positive
o Because of these bonds they have higher boiling points than alkanes (and aldehydes/ketones)
- positional isomerism= propan-1-ol or propan-2-ol
- there are three types of alcohols:
o primary - the carbon with hydroxyl group is attached to only 1 other carbon (the end of molecule)
 can be oxidized into aldehydes and further into carboxylic acids
o secondary - the carbon with hydroxyl group is attached to 2 other carbons (anywhere in the middle)
 can be oxidized into ketones
o tertiary - the carbon with hydroxyl group is attached to 3 other carbons (C with some other C group)
 cannot be oxidized

How is alcohol produced? 1. Fermentation 2. Distillation- (getting rid of methanol and water)
- Yeast turns sugar into alcohol (sugar -> CO 2 + C2H6O) ... we need sugar, water, yeast
- Product = mixture of water and about 15% ethanol, no more alcohol is produced because the yeast
is denatured by the alcohol (you can also poison yeast by too much sugar)
- ADVANTAGES: renewable resources, less energy used

OR Hydration of ethene as means of producing ethanol:

- Equilibrium reaction, temp.: 570K, press.: 6-7 Mpa?
- ADVANTAGES: atom economy of 100%, high yield of ethanol, fast react., continuous process, purer product
- H3PO4 (phosphoric acid - PA) is in this reaction used as catalyst
o All hydrogens in PA are slightly +, because they are attached to highly electronegative atom-oxygen

1. step: one of hydrogen from PA is highly attracted to the carbon double bond in ethene
o H (slightly +) seeks electrons that can be found in the double bond
- Double bond breaks and the compounds takes the hydrogen, new compound has single bond while missing
one hydrogen to be ethane, so it has slightly positive charge on the Carbon that is missing it
- The PA lacks the hydrogen atom, so it becomes dihydrogen phosphate with negative charge on oxygen
(because it is so electronegative that it gained control over the electron that belonged to hydrogen in the
previous bond… or we know that it should be attached to 2 (charge -2) atoms and it ISNT)

2. step: the “nearly ethane”, that carries positive charge, is electrophile because it needs electron to become neutral
- The water in this case is nucleophile… So, they combine to make something like ethanol, but with one more
hydrogen on the oxygen than ethanol has, that’s why this compound has positive charge on oxygen
o Or we just know combining neutral and positive compound yields positive compound

3. step: the “nearly ethanol”, that carries positive charge, gives its hydrogen to the negative dihydrogen phosphate
- We get back phosphoric acid and ETHANOL!!! That was unnecessarily long explanation for simple equation