Help on an OCHEM question

[Amber Q]

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Hi guys,
I am having trouble understanding this reaction. Can someone break it down for me.

CH3CH2CH2CH2OH H2SO4,heat CH3CH2CH2CH2OCH2CH2CH2CH3

I do not understand how the product is an ether. I thought H2SO4 would dehydrate the alcohol and make an Alkene. And ether synthesis would require a base to deprotonate and an alkyl halide to make the ether.
I am confused.
Thanks for helping.
Amber

 

[threechins]

It's an acid catalyzed condensation of alcohol.
Here's a link for the mechanism.
http://www.chem.ucalgary.ca/courses/350/Carey5th/Ch15/ch15-4-4-1.html

 

[bluesolic]

Hi guys,
I am having trouble understanding this reaction. Can someone break it down for me.

CH3CH2CH2CH2OH H2SO4,heat CH3CH2CH2CH2OCH2CH2CH2CH3

I do not understand how the product is an ether. I thought H2SO4 would dehydrate the alcohol and make an Alkene. And ether synthesis would require a base to deprotonate and an alkyl halide to make the ether.
I am confused.
Thanks for helping.
Amber

after, OH takes another H from the H+, it will becomes h20+

and then, either it can be taken off the H from C by other molecule (E2) becomes alkene, or another butanol kick out the H2O+ (SN2).

however, in this case, there is no molecule which can take place E2 rxn, only thing drives the rxn next is SN2 so it must form ether.

 

[Amber Q]

Thank you. That explains it.

 

[bluesolic]

Thank you. That explains it.

After I answered this question, I've kept thinking about this and I figured out that the product also must be alkene and I think the major product should be alkene not ether.


The reason is that the heat will drive the E2 rxn by removing water.

ether also came out and also,

CH3CH2CHCH2
O
CH2CH2CH2CH3 ALSO CAME OUT.. after alkene rxn with butanol..


I am pretty sure,,

you know what, I always feel like DAT destroyer and other practice exam are so stupid because of kind of this questions.

any of rxn in Ochem is not produced just one solid product ..

so, in the questions, they should have options like four non-sences with one possible answer so that we can get the answer.

this rxn will have 3 product, and ONLY one of them SHOULD be on the options in the question.


was it from DAT practice exam ?