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

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:
1-methyl
cyclohexanol
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 product = most substituted H C CH3 H H3C H H C C H 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 product =
most substituted

11. What are dehydration products of 1-methylcyclohexanol?
CH3 H

12. Alcohols Condensation Reaction CH3 – OH + HO – CH3 CH3 – O – CH3 + H2O
H2SO4
CH3 – OH +
HO – CH3
CH3 – O – CH3
+ H2O
two molecules combine to form
larger molecule + water
ether
H2O
alcohol +
alcohol +

13. Ethers O- - R water alcohol ether H-bond acceptor no H-bond donor
dipole-dipole interactions
low b.p.
soluble in polar solvents

14. Ethers Common nomenclature : name both R groups + ether propyl2 1 3 1
methyl propyl
ether
methyl
methyl
dimethyl ether O
methyl

15. Ethers Reactions Formation: Peroxide formation: condensation reaction
H2SO4
condensation reaction
Peroxide formation:
peroxide