[vkeeton]

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.

[chenbeier]

What kind of problems do you observe?  Beside Butanole also butene will be developed? Need process conditions.

Later need destillation Chlorbutane and butanole

[OrganicDan96]

what side reaction might you think is occurring. how are you visualising the TLC?

[vkeeton]

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.

[OrganicDan96]

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?

[vkeeton]

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.

[rolnor]

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?