1. Alcohols .. organic analog of water Hydrogen bond donor O-Hd+ Od-
Hydrogen bond acceptor
- 42oC
boiling point
propane
ethanol
+ 78 oC

2. Alcohols Solubility in H2O (g/100 mL) formula boiling point H3C O H O
C2H5OH miscible
C4H9OH
CH3OH 65
miscible
C6H13OH
C8H17OH insoluble
H3C O H d+ d- O H d+ d-
CH2CH2CH3
CH2
CH2CH2CH2H2C
H3C O H
H3C O H d+ d-

3. Alcohols - Nomenclature
1. Longest continuous chain with - OH
2. Root name + “-ol”
3. Position of - OH given smallest number
4. Ring of cyclic alcohols numbered from - OH
5. Compounds with more than one - OH called
“diols” or “triols”

4. Alcohols 4-ethyl- 3- heptan ol 6-methyl- 2,4- octane diol phenol 6 4 27 1 5 3 2 4 5 3 1
6-methyl-
2,4-
octane
diol 6 7 8
phenol

5. classes of alcohols 1o alcohol 1- butanol 2o alcohol 2- propanol4 3 2 1 1-
butanol
2o alcohol 2-
propanol
3o alcohol
2-methyl- 2-
propanol

6. Alcohols Classify and name: 1o 2o 3o 1-methyl cyclohexanol 1o
2-phenyl-
1-propanol

7. Alcohols - reactions dehydration reverse of hydration of alkenes
a) electrophile
b) nucleophile
step 1 C H O : C H OH H+ : : H+

8. C H O :
step 2 C H O H : +
step 3 C H
+ H+
regenerate catalyst

9. hydration - dehydration
+ H2O
[alcohol]
Q =
K = 5
[alkene]
[H2O]
G =
-RT ln K/Q

10. 2-butanol major minor major product = most substituted H C CH3 H H3C H4 1 2 3
2-butanol H 4 3 C
CH3 H 1
H3C H 1 2 H 2 3 C C H H 4
CH3 H
1-butene
trans-
2-butene
major
minor
major product =
most substituted

11. What are dehydration products of 1-methylcyclohexanol?
a) major product
b) minor product
CH3 H H
major product

12. Oxidation of alcohols Primary alcohols: carboxylic acid 1o alcohol1+ 2- 2- 2- 1+ 1- 3+ 1+ 1+ 1+ 1+ 2-
carboxylic acid
1o alcohol
aldehyde
[O] = oxidizing agent
dichromate
Cr2O72-
Cr3+
permanganate
MnO4-
oxidation =
loss of e- density from C
1. binding O
2. removing H

13. Oxidation of alcohols Secondary alcohols: 2o alcohol ketone
no reaction
2o alcohol
ketone

14. Oxidation of alcohols
Tertiary alcohols:
no reaction