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-
weak oxidizing agent
PCC
1o alcohol  aldehyde
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- or PCC [O] [O]
2o alcohols
ketone
no reaction
[O]

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

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

6. 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”)

7. 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

8. 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

9. 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

10. Reactions
Reduction:
LiAlH4
H2/ Pt
NaBH4

11. Alkanes
CnH2n+2
conformations (Newman)
optical isomers
LDF
CnH2n
cyclic
geometric isomers
combustion
halogenation

12. Alkyl halides
Nucleophilic substitution 1o
SN2
transition state
inversion of stereocenter 3o
SN1
carbocation
racemic mixture 2o ?

13. Alkenes
sp2
CnH2n
geometric isomers
Addition reactions
H – X
H – OH
H – H
Br – Br
polymerization

14. Alcohols
CnH2n+2O
H-bonding
dehydrate
most substituted alkene
oxidize 1o
aldehyde
carboxylic acid 2o
ketone 3o
no reaction
condensation
2 alcohol  ether + water

15. reduction
aldehyde
CnH2nO
 1o alcohol
H2/Pt, NaBH4, LiAlH4
CnH2nO
ketone
 2o alcohol
H2/Pt, NaBH4, LiAlH4
carboxylic acid
CnH2nO2
 1o alcohol
only LiAlH4