1. Oxidation of alcohols 1o alcohol aldehyde carboxylic acid1+ 2- 2- 2- 1+ 1- 3+ 1+ 1+ 1+ 1+ 2-
1o alcohol
aldehyde
carboxylic acid
[O] = oxidizing agent
dichromate
Cr2O72-
Cr3+
permanganate
MnO4-
oxidation =
loss of e- density from C
1. binding O
2. removing H

2. Alcohols oxidation of alcohols: [O] = Cr2O72- or MnO42- [O] [O]
1o alcohols
aldehyde
carboxylic acid
[O]
[O] +
Cr3+ +
Cr2O72-
methanol
methanal
methanoic acid
formaldehyde
formic acid

3. Alcohols oxidation of alcohols: [O] = Cr2O72- or MnO42- [O] [O]
2o alcohols
ketone
no reaction
[O]

4. Alcohols oxidation of alcohols: [O] = Cr2O72- or MnO42- [O]
3o alcohols
no reaction

5. 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 +

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

7. Ethers “ether” bunny Common nomenclature : name both R groups + ether
propyl 2 1 3 1
methyl propyl
ether
methyl
methyl
dimethyl ether O ..
methyl
“ether” bunny
propyl
people
ether

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

9. Aldehydes and Ketones C=O 120o aldehyde ketone carbonyl group
C and O are sp2 hybridized

10. Aldehydes and Ketones Nomenclature 1. Longest chain with C=O is parent
2. Suffix is “-al” or “-one”
3. C1 is always C=O in aldehydes
In ketones, C=O is given lowest number
4. C=O has precedence over -OH
(called “hydroxy”)

11. 2-bromo-3-methyl butan al 3- pentan one trans- 3-hydroxy- 2-methyl4 2 1 3-
pentan
one 1 4 2 5 3
trans- 1 2
3-hydroxy-
2-methyl
cyclobutanone 3

12. Physical properties O .. C H O .. C H : - polar+ + -
polar
higher b.p. than alkanes
H-bond acceptor
soluble in polar solvents
no H-bond donor
lower b.p. than alcohols

13. Reactions Reduction [R] = reducing agent LiAlH4 NaBH4 H2/Pt butan al3 1 2
CH3-
CH2-
CH2-
CHO
CH3-
CH2-
CH2-
CH2- OH
butan al
[R] 1 3 4 2 2-
butan
one