Copperacetate Ammonium Nitrate Oxidation Of Benzoin To Benzil
SYNT m o d u l a r
·
l a b o r a t o r y
·
p r o g r a m
·
i n
·
publisher: H. A. Neidig
c h e m i s t r y
738
organic editor: Joe Jeffers
Copper-Catalyzed Oxidation of Benzoin to Benzil prepared by Carl T. Wigal, Lebanon Valley College
PURPOSE OF THE
EXPERIMENT
Oxidize benzoin to benzil using ammonium nitrate and copper(II) ion as a catalyst, monitoring the reaction by thin-layer chromatography.
Characterize the product using melting point measurement and infrared spectroscopy.
EXPERIMENTAL OPTIONS
Semi-Microscale Oxidation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
Microscale Oxidation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
BACKGROUND REQUIRED
You should be familiar with making micropipets, vacuum filtration, recrystallization, melting point measurement, thin-layer chromatography (TLC), and infrared spectroscopy (IR).
BACKGROUND
INFORMATION
An important category of chemical reactions involves the transfer of electrons from one molecule to another. These reactions, called oxidation– reduction or redox reactions, are used to synthesize a large variety of compounds. Redox reactions also control energy flow in biological systems. In a redox reaction, one atom or molecule loses electrons while another gains electrons. In organic reactions, the gain or loss of electrons is not always clear. Consequently, organic chemists define redox in terms of the loss or gain of carbon–hydrogen bonds. An organic oxidation is defined as the loss of carbon–hydrogen bonds, while an organic reduction is defined as a gain of carbon–hydrogen bonds. In an organic oxidation, a bond involving a more electronegative element, usually oxygen, replaces the carbon–hydrogen bond. The various oxidation states of a carbon atom are shown in Equation 1. The symbol [O] indicates an unspecified oxidizing agent.
H
H C H
[O]
H
H C OH
H
H
methane
methanol
O
[O]
H
C
O
[O]
H
formaldehyde
H
C
·
l a b o r a t o r y
·
p r o g r a m
·
i n
·
publisher: H. A. Neidig
c h e m i s t r y
738
organic editor: Joe Jeffers
Copper-Catalyzed Oxidation of Benzoin to Benzil prepared by Carl T. Wigal, Lebanon Valley College
PURPOSE OF THE
EXPERIMENT
Oxidize benzoin to benzil using ammonium nitrate and copper(II) ion as a catalyst, monitoring the reaction by thin-layer chromatography.
Characterize the product using melting point measurement and infrared spectroscopy.
EXPERIMENTAL OPTIONS
Semi-Microscale Oxidation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
Microscale Oxidation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
BACKGROUND REQUIRED
You should be familiar with making micropipets, vacuum filtration, recrystallization, melting point measurement, thin-layer chromatography (TLC), and infrared spectroscopy (IR).
BACKGROUND
INFORMATION
An important category of chemical reactions involves the transfer of electrons from one molecule to another. These reactions, called oxidation– reduction or redox reactions, are used to synthesize a large variety of compounds. Redox reactions also control energy flow in biological systems. In a redox reaction, one atom or molecule loses electrons while another gains electrons. In organic reactions, the gain or loss of electrons is not always clear. Consequently, organic chemists define redox in terms of the loss or gain of carbon–hydrogen bonds. An organic oxidation is defined as the loss of carbon–hydrogen bonds, while an organic reduction is defined as a gain of carbon–hydrogen bonds. In an organic oxidation, a bond involving a more electronegative element, usually oxygen, replaces the carbon–hydrogen bond. The various oxidation states of a carbon atom are shown in Equation 1. The symbol [O] indicates an unspecified oxidizing agent.
H
H C H
[O]
H
H C OH
H
H
methane
methanol
O
[O]
H
C
O
[O]
H
formaldehyde
H
C