Chem 212

Aldehyde and ketone problems 2

H H
OH O 1) EtMgBr
CrO3, H2SO4

2) H3O+
H H
O CH3CH2CH2NH2
HO
OH
pH = 4.5 O
H+ catalyst

O H2, Pd/C NH2

O 1) pH 4.5

2) NaBH4, MeOH

O CrO3, H2SO4 O
Zn/Hg
H
HCl

O MeOH
HO
H+ catalyst NH2OH, H+
O

1) PPh3
O HCN, cat. NaOH
Br 2) nBuLi
3) acetone

NH2NH2, KOH
O
OH CrO3, pyridine

O
NaBH4
Me2NH, H2O
EtOH
O pH 4.5
O
O H+, H2O NHNH2
benzaldehyde
O
O2N NO2 pH 4.5
Cl
Cl
H H+, H2O
Cl H
O N pH 4.5
O +

CHO
OH
O H OH H+
H+, H2O
H OH
O CH2OH
HO

H
Ph3PCH2Ph

O O KOH
1) LiAlH4

2) H+, H2O
1) Ph3P
Br 2) nBuLi
3) propenal
O
SH
HS
1) Mg, ether
ZnCl2 Br
2) propenal
3) H3O+

O
Br H3O+
H CrO3
O O
Br H2SO4