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Title: Aldehydes and ketones synthesis
Description: Well Comprehensive notes on Aldehydes and ketones nomenclature
Description: Well Comprehensive notes on Aldehydes and ketones nomenclature
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SCH 206
Synthesis of Aldehydes and Ketones
Aldehydes and Ketones
Hydration
Alkynes
Dr
...
Oxidation of Alcohols
OH
Oxidizing agent
H
R
H
1° Alcohol
SCH 206
Aldehyde
Oxidation of a primary alcohol to an aldehyde requires
careful selection of an oxidizing agent, since they are
easily oxidized to carboxylic acids
...
Solomon Derese
Ketone
18
SCH 206
OXIDIZING AGENTS
Aqueous oxidants
Anhydrous oxidants
H2CrO4
Na2Cr2O7
K2Cr2O7
N
H
ClCrO3
Pyridinium chlorochromate (PCC)
KMnO4
Dr
...
Dr
...
1° Alcohol
Aldehyde (not isolated)
Dr
...
Solomon Derese
22
SCH 206
Step I: Formation of a chromate ester
Step II: E2 elimination to form a carbon-oxygen p bond
Dr
...
Dr
...
Solomon Derese
Green
25
Assignment 5
SCH 206
I
...
Provide a step by step mechanism for the
following transformation:
Dr
...
OZONOLYSIS OF ALKENES
General reaction
R
H
O3
:O :
:O :
:O :
R
R
R
R
H
R
R
R
Molozonide
O
H
O O R
Ozonide
Reductive workup
Oxidative workup
O H
R
O+ O
R
Dr
...
O
...
R
H
R
R
R
R
Molozonide
R
R
R
Dr
...
O
:O:
O
H
R
R
H
O O R
Ozonide
H
...
:O
...
O3
2
...
O3
2
...
H3O+
O
O
HO
Dr
...
Hydration of Alkynes
H
R
H
H
OH
R
H
HgSO4, H2SO4, H2O
Markovinikov
addition
1) BH3 / THF
2) H2O2, -OH, H2O
Anti-Markovinikov
addition
Tautomerization
HO
Enol
Keto
Terminal alkynes undergo addition of water in the
same way as alkenes, except that the product is an
enol
...
Dr
...
Terminal alkynes will add
water if mercuric ion, Hg2+, is added to the acidic
mixture
...
Internal alkynes
undergo hydration with concentrated acid
...
Dr
...
Dr
...
Dr
...
Friedel-Crafts acylation
SCH 206
General reaction
AlCl3
Example
Dr
...
Cl :
...
AlCl
Cl
3
...
C O
...
Solomon Derese
35
SCH 206
Step II: Electrophilic attacks
O
C
H
O
R
R
Cl
...
Al Cl
Cl
O
R
Dr
...
Dr
Title: Aldehydes and ketones synthesis
Description: Well Comprehensive notes on Aldehydes and ketones nomenclature
Description: Well Comprehensive notes on Aldehydes and ketones nomenclature