Experiment 8 Preparation of Cyclohexanone by Hypochlorite Oxidation

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I need help to find the mechansim for  Preparation of Cyclohexanone by Hypochlorite Oxidation and explain the mechanism in detail 

Experiment 8
Preparation of Cyclohexanone by Hypochlorite Oxidation
In this experiment we will prepare cyclohexanone from cyclohexanol using hypochlorite oxidation. We
will use common household bleach that is a 5.25% (0.75 M) aqueous solution of sodium hypochlorite. The
overall reaction is shown in Figure 8.1.
Figure 8.1 Oxidation of Cyclohexanol
Na*
OCI
CH;
HOCI
CH:
Na*
sodium hypochlorite
acetic acid
OH
HOCI
H2O
HCI
cyclohexanol
cyclohexanone
The exact reaction mechanism is not known but a plausible mechanism is given below. It is known that
the mechanism does not involve free radicals and that yields are better in acidic rather than basic conditions.
This is why we use acetic acid. It reacts with the sodium hypochlorite to give hypochlorous acid, which then
reacts with the oxygen of the alcohol. Note the oxygen is more electronegative than chlorine so the oxygen
attacks the chlorine of the hypochlorite, which has a formal charge of +1.
Figure 82 Mechanism for Oxidation
H;C
H
-OH
H2O
+ H,0 + CF
Physical Constants
Compound
Mol. Wt (g/mol)
Density
(g/mL)
b.p. (°C)
m.p. (°C)
Cyclohexanol
Cyclohexanone
Dichloromethane
100.16
0.96
161.5
25.5
98.15
0.947
155
-47
84.93
1.325
39-40
-97
Transcribed Image Text:Experiment 8 Preparation of Cyclohexanone by Hypochlorite Oxidation In this experiment we will prepare cyclohexanone from cyclohexanol using hypochlorite oxidation. We will use common household bleach that is a 5.25% (0.75 M) aqueous solution of sodium hypochlorite. The overall reaction is shown in Figure 8.1. Figure 8.1 Oxidation of Cyclohexanol Na* OCI CH; HOCI CH: Na* sodium hypochlorite acetic acid OH HOCI H2O HCI cyclohexanol cyclohexanone The exact reaction mechanism is not known but a plausible mechanism is given below. It is known that the mechanism does not involve free radicals and that yields are better in acidic rather than basic conditions. This is why we use acetic acid. It reacts with the sodium hypochlorite to give hypochlorous acid, which then reacts with the oxygen of the alcohol. Note the oxygen is more electronegative than chlorine so the oxygen attacks the chlorine of the hypochlorite, which has a formal charge of +1. Figure 82 Mechanism for Oxidation H;C H -OH H2O + H,0 + CF Physical Constants Compound Mol. Wt (g/mol) Density (g/mL) b.p. (°C) m.p. (°C) Cyclohexanol Cyclohexanone Dichloromethane 100.16 0.96 161.5 25.5 98.15 0.947 155 -47 84.93 1.325 39-40 -97
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