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Organic 16 Online
OpenStudy (anonymous):

Draw the major neutral organic products

OpenStudy (anonymous):

OpenStudy (joannablackwelder):

I think that the first one would be|dw:1429821057712:dw|

OpenStudy (joannablackwelder):

Based on http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/addyne1.htm under Acidity of Terminal Alkynes

OpenStudy (joannablackwelder):

Does that make sense to you?

OpenStudy (anonymous):

I understand the 1st one, its the second one I don't understand. I know it'll go under an elimination, because its not a primary alkyl halide

OpenStudy (joannablackwelder):

Well, I got a different answer than you for the first one. Which one do you think is correct?

OpenStudy (anonymous):

yours is, i never finished the problem

OpenStudy (joannablackwelder):

Oh, ok. I think the second one basically does the same thing as the first.

OpenStudy (joannablackwelder):

Want to try to finish it based on the same idea as the first one?

OpenStudy (anonymous):

for the second one its not a primary alkyl halide, its tertiary so im unsure how to draw the product

OpenStudy (joannablackwelder):

That's true. Let me look into that.

OpenStudy (anonymous):

okay thank you!

OpenStudy (joannablackwelder):

Sure. :-) Apparantly, 2º and 3º-alkyl halides undergo elimination by an E2 mechanism. But I haven't been able to figure out what that means yet.

OpenStudy (joannablackwelder):

In the context of this problem.

OpenStudy (aaronq):

It's basically the same thing, you end up with |dw:1429823281379:dw|

OpenStudy (aaronq):

E2 means bimolecular, where both molecules (in this case the the deprotonated alkyne and the alkylhalide) interact - opposed to an E1 mech where the Br would first leave the tertiary alkylhalide

OpenStudy (anonymous):

that one is incorrect.

OpenStudy (aaronq):

can you post a screen shot?

OpenStudy (aaronq):

it's possible that you drew it wrong?

OpenStudy (anonymous):

it wanted the starting product as well

OpenStudy (nincompoop):

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