Another Organic Question???

[futuredds1101]

on kaplan's complete science integration workshop B, # 85, what is the product of: KOH
n-propyl chloride ------> ?

since KOH can act as both a strong base and strong nucleophile, and the substrate is a primary alkyl halide, should the product not be n-propyl alcohol (choice C) via a SN2 rxn? the answer key has propylene has the answer which is via E2 mechanism but i don't think this is right. is this another kaplan mistake or am i wrong? thanks.

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[ippie]

I agree with you. I think the solution is wrong. I had the same problem when I solved that problem. Kaplan has some mistakes.

on kaplan's complete science integration workshop B, # 85, what is the product of: KOH
n-propyl chloride ------> ?

since KOH can act as both a strong base and strong nucleophile, and the substrate is a primary alkyl halide, should the product not be n-propyl alcohol (choice C) via a SN2 rxn? the answer key has propylene has the answer which is via E2 mechanism but i don't think this is right. is this another kaplan mistake or am i wrong? thanks.

 

[cryptozoologist]

It's not wrong, any 2prime carbon combined with strong base always goes to E2. it only goes to SN2 via weak base/good nucleophile.

 

[Notoriousjae]

on kaplan's complete science integration workshop B, # 85, what is the product of: KOH
n-propyl chloride ------> ?

since KOH can act as both a strong base and strong nucleophile, and the substrate is a primary alkyl halide, should the product not be n-propyl alcohol (choice C) via a SN2 rxn? the answer key has propylene has the answer which is via E2 mechanism but i don't think this is right. is this another kaplan mistake or am i wrong? thanks.

this has already been discussed heres the link

http://forums.studentdoctor.net/showthread.php?t=297193