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Topic: cyclohexanol to cyclohexanone  (Read 10528 times)

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Offline Charkol

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cyclohexanol to cyclohexanone
« on: November 21, 2010, 10:58:54 AM »
Can someone help me balance this reaction to the goal of knowing how much cyclohexanone to expect?

First
10mol of H-OH + .08mol of Na2Cr2O7*H2O + .09mol H-OSO3H + .2 cyclohexanol -->
--> heated to 55-60C for one hour.  This made cyclohexanone. 

The amounts shown in the reaction are the amounts used. 

How would I find the general mole ratio for this reaction?  I found at some random site on the internet that it is

[3mol of cyclohexanol] to
[1mol of sodium dichromate dihydrate] to
[8mol of H+]

Is this correct?  I tried following the mechanism for this reaction, called chromic acid oxidation of a 2nd degree alcohol, in the book we have(Solomons Organic Chemistry, 10e), but it is a extremely generalized mechanism and doesn't give specifics.

Offline democanarchis

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Re: cyclohexanol to cyclohexanone
« Reply #1 on: November 21, 2010, 01:33:09 PM »
What is the limiting reagent in this reaction?

Offline Charkol

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Re: cyclohexanol to cyclohexanone
« Reply #2 on: November 21, 2010, 02:45:28 PM »
What is the limiting reagent in this reaction?

Exactly! From my perspective the limiting reagent would depend on the properly balanced equation.  As I am trying to determine the mole ratios for this reaction I am stuck at the balancing part.

If the mole ratio from the random website that I mentioned is correct, the limiting reagent would be the sulfuric acid, and I could proceed from there.  But I am not sure that this is correct. 

Offline democanarchis

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Re: cyclohexanol to cyclohexanone
« Reply #3 on: November 21, 2010, 04:28:20 PM »
Is it possible that the amount of sulfuric acid is only catalytic? What is the starting material for the cyclohexanone?

Offline Charkol

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Re: cyclohexanol to cyclohexanone
« Reply #4 on: November 21, 2010, 04:51:00 PM »
Is it possible that the amount of sulfuric acid is only catalytic? What is the starting material for the cyclohexanone?

So, the sulfuric acid is only providing the protons to acidify the dichromate, then two molecules of H-OSO3H would be required for full acidification of the dichromate molecule.

If the protonated dichromate was completely saturated with H+, then as long as there was a sufficient amount of cyclohexanol the dichromate would be the limiting factor, yes?

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