March 27, 2015

Homework Help: Chemistry Check

Posted by ramire2 on Friday, November 8, 2013 at 2:28am.

Just want to make sure that my thought process is right on this one.

5 compounds:

n-butyl chloride
n-butyl bromide
sec-butyl chloride
tert-butyl chloride
and crotyl chloride

Each is reacted with NaI (SN2?) and AgNO3 (SN1?)

And we have to rank the reaction time and wether we think a reaction would occur or not.

So SN1 is allyl > tert > sec> primary>>methyl
by carbocation stability. So I think crotyl chloride is considered an allyl by the double bond in structure so fastest to slowest would be: crotyl> tert-butyl chloride> sec-butyl chloride> n-butyl bromide> n-butyl chloride (slowest because Br is better leaving group?)
As far as reaction goes, I don't think primary can go SN1, so the last two would be no reaction

As for SN2 NaI it's ranked by hinderance so
crotyl?>n-butyl chloride>n-butyl bromide> sec. > tert.
And I know tert. can't go SN2 so no reaction for that one.

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