Destroyer Orgo 2010-q 166

[JNew]

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I understand the answer, I just want to know why in the explanation he says it goes SN2 if we are in a polar protic solvent which should go SN1. Unless it's because a primary halide is hardly reactive in SN1, so it must be SN2?

 

[JNew]

Also, if anyone has an explanation for 168 why the big bulky base c) is better than the regular base e)...

 

[RCT PC CRN]

Primary halide - SN2

Halide we have is Primary so it will go SN2

 

[RCT PC CRN]

168

We have Primary halide and we would like to do E2 - Order of reactivity for any elimination is 3-2-1 (decreasing order) ...hard to do elimination with primary but if we use right condition then it's possible.

We make sure that we don't use good Nu or else it would do Substitution (SN2) specially since we have primary halide...hindered base are worst/weak Nu...t-but is our best bet here.

A. CH3OH - weak base/weak Nu - most probably no reaction
B. OH- - strong base/strong Nu - with primary it will do Substitution
D. KI - I ion is weak base (conj base of strong acid) but also the world best LG so hard to do any substitution or elimination reaction with it.
E. C2H5O- +k - charged base - good Nu - with primary halide it will do SN2

So the answer is C

I hope this help