So I\'ve posted this question like three times and have gotten different answers

Question

So I've posted this question like three times and have gotten different answers for each posting. Can someone explain how to get started with this question and what I should be looking at to solve it? I just don't get how you find out if its 1, 2 or 3. I know SN2 favors 1 and SN1 favors 3, but how do I find that?

Decide the mechanism by which the following alkyl halides will be converted to alcohols by the substitution of the nucleophile, OH-.

R-X + OH- ? R-OH + X-

SN1 SN2 more information needed  1-chloro-3-methylbutane
SN1 SN2 more information needed  1-bromo-1-methylcyclohexane
SN1 SN2 more information needed  bromocyclopentane
SN1 SN2 more information needed  3-chloro-3-ethylpentane

I've posted this twice. It's not SN2, SN1, SN2, SN1. It doesn't work.

Explanation / Answer

1) 1-chloro-3-methylbutane ---------------> SN2

becaue chloro group is attached to primary carbon and thus SN2 is preferred in presence of stroong base.

2) 1-bromo-1-methylcyclohexane ----------> SN1

becaue bromo group is attached to tertiary carbon and thus SN1 is preferred in presence of stroong base.

3) bromocyclopentane ---------------> both SN1 and SN2

becaue bromo group is attached to secondary carbon and thus SN1 is preferred in presence of strong base and SN2 is also possible as attack of OH- is also possible from the back side.

4) 3-chloro-3-ethylpentane -------------> SN1

becasue

becaue chloro group is attached to tertiary carbon and thus SN1 is preferred in presence of stroong base.

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