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Topic: Question about haloalkanes and reactivity  (Read 2474 times)

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Offline gg66

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Question about haloalkanes and reactivity
« on: December 16, 2015, 04:30:16 PM »
Can someone please explain why the answer is B and not D in this picture attached in the link?

http://puu.sh/lY7yD/bb7fb5e834.png

Offline Babcock_Hall

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Re: Question about haloalkanes and reactivity
« Reply #1 on: December 16, 2015, 04:34:00 PM »
Can you explain your thinking first?  BTW I see that you drew CH3+.  Can you explain why?

Offline gg66

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Re: Question about haloalkanes and reactivity
« Reply #2 on: December 16, 2015, 04:40:28 PM »
Well I thought that once the I leaves, it's taking the electrons with it, and there would be a positive charge left on the C as it doesn't have a full octet anymore. And since that C only has hydrogens, it's the least stable and would thus react with water the fastest.

Offline Babcock_Hall

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Re: Question about haloalkanes and reactivity
« Reply #3 on: December 16, 2015, 04:50:19 PM »
Haloalkanes can react by one of two mechanisms.  One is as you describe, and it is called the SN1 mechanism.  However, there is also a mechanism in which the nucleophile gives the carbon atoms a pair of electrons simultaneously (in a concerted manner) with the departure of the electron pair with the halogen.  This is called the SN2 mechanism.  Did you cover these two in class?

Offline gg66

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Re: Question about haloalkanes and reactivity
« Reply #4 on: December 16, 2015, 05:01:55 PM »
Oh yes, we did! So D is going by SN2 and B by SN1. I'm still not seeing why B is more favored  :(

Offline Babcock_Hall

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Re: Question about haloalkanes and reactivity
« Reply #5 on: December 16, 2015, 05:33:34 PM »
I think you are correct with respect to matching the mechanism to the substrate.  The only explanation that occurs to me at the moment is that water is a poor nucleophile.  A poor nucleophile will produce slow SN2 reactions but not SN1 reactions.  However, my opinion is that it is a difficult question.

Offline gg66

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Re: Question about haloalkanes and reactivity
« Reply #6 on: December 16, 2015, 05:37:12 PM »
Ahh I see, that would make sense! I think that would explain it, thank you!

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