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Old Oct 28th 2017, 10:31 PM   #1
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Join Date: Oct 2017
Location: Terre Haute
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Acid Base and S1 E2 Sn1 Sn2 Help

I'm in the beginning of my chemistry major and am having trouble with organic chemistry. I feel like for the most part when dealing with reactions I know what drives most reactions to what type but when I sit down at a quiz or test I have trouble putting it all together. We've been given a take home quiz and I've done the vast majority of it but don't feel confident and have a few questions. I'm going to try to include pictures of it.

On problems both a and g it seems to me an acid/base reaction will occur first thus the deprotonation and then the formation of the ring via an SN2 reaction. However, the weak base in an aprotic solvent on problem a gives me some doubt. I basically just wanted to know if there's any reason the acid base reaction would not occur and instead simply an SN2 reaction.

On question g I strongly suspect an acid vase reaction as well and despite the protic solvent, an SN2 since a primary carbocation would be unlikely. Also since the methyl groups are on a neighboring carbon that does not undergo any changes so they should keep their stereochemistry.

On problem c I figured no reaction due to it being an sp2 alkyl halide. I don't full understand why this is, we were simply instructed this would not occur in lecture.

On question e, well I simply don't see anything... I'm lost on it. I understand that the hydroxide is a good nucleophile and strong base, but on the substrate I don't see anything that would react as a good leaving group or anything for that matter. But for some reason my gut is telling me some sort of reaction will occur.

I honestly just feel lost in all of this and would greatly appreciate any advice and or correction on any misconceptions I seem to have or have articulated here.
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