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Topic: Butanol Synthesis  (Read 423 times)

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Offline vkeeton

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Butanol Synthesis
« on: February 08, 2019, 02:16:28 PM »
Hello All!

I have been working on my Organic Chemistry Lab for about a week with no success. It is nucleophilic substitution and my target compound is butanol. My starting reagent is chlorobutane with ether as my solvent, I then add KOH. My TLC readings don't provide much information. Once time has passed, I am left with 1-butanol, water, and potassium chloride but cannot get a pure compound of butanol. I am at my wits end with this. Does anyone have any ideas or suggestions? Thank you so much in advance.

Offline chenbeier

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Re: Butanol Synthesis
« Reply #1 on: February 08, 2019, 02:58:35 PM »
What kind of problems do you observe?  Beside Butanole also butene will be developed? Need process conditions.

Later need destillation Chlorbutane and butanole


Offline OrganicDan96

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Re: Butanol Synthesis
« Reply #2 on: February 08, 2019, 03:36:29 PM »
what side reaction might you think is occurring. how are you visualising the TLC?

Offline vkeeton

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Re: Butanol Synthesis
« Reply #3 on: February 08, 2019, 03:46:28 PM »
Everything is being done in a virtual lab so the TLC plates are part of the program. There is only one spot showing and there is no movement throughout the reaction. I know I should be able to see the chlorobutane and the butanol, but I cannot.

Offline OrganicDan96

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Re: Butanol Synthesis
« Reply #4 on: February 08, 2019, 03:50:16 PM »
Everything is being done in a virtual lab so the TLC plates are part of the program. There is only one spot showing and there is no movement throughout the reaction. I know I should be able to see the chlorobutane and the butanol, but I cannot.
maybe you are not getting the desired product? do you know of another reaction might occur and why you might not see it?

Offline vkeeton

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Re: Butanol Synthesis
« Reply #5 on: February 08, 2019, 04:09:07 PM »
I am given the the following reagent for my starting materials:
Chlorobutane
4-chloro-1-butanol
2-chloro-2-methyl propane
Benzyl chloride
2-chloro-norbornane

I have to use Ether as my solvent

Reagents to synthesize:
OSO4
KOH
LDA
HNO3
SOCL2
NaOMe
H2Cr2O2
Br2
Bh3
HCL
H2SO4
PCC
NaBh4
AlCl3
MCPBA

I start with the cholorobutane and add the ether then add the KOH

My screen shows:
Cholorobutane
Diethyl ether
Potassium Hydroxide

I add the heater, condenser and N2 gas and after 10 mins, I now have:
Cholorobutane
Diethyl ether
Potassium Hydroxide
1-butanol
Potassium Chloride

After 10 more mins, I have:

Diethyl ether
1-butanol
Potassium Chloride

I then use the separtory funnel and add H2O but I am able to separate the diethyl ether out and cannot get pure butanol.

Offline rolnor

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Re: Butanol Synthesis
« Reply #6 on: February 08, 2019, 04:43:10 PM »
I think it all seems strange, KOH is not soluble in ether and can not react with the chlorobutane? Can you filter of the KCl and then distill the ether/butanol mixture?

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