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Topic: SCH3-  (Read 34517 times)

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Offline portugal

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SCH3-
« on: March 03, 2008, 05:31:53 AM »
Since NaSCH3 is a weak base but a very strong nucleophile this means that alkyl halides undergoes an SN2 substitution rather and elimination is that right or not??

Offline azmanam

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Re: SCH3-
« Reply #1 on: March 03, 2008, 06:10:56 AM »
Knowing why you got a question wrong is better than knowing that you got a question right.

Offline portugal

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Re: SCH3-
« Reply #2 on: March 03, 2008, 06:38:11 AM »
well its a primary alkyl halide and therefore its a substitution according to that page is that right?

Offline azmanam

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Re: SCH3-
« Reply #3 on: March 03, 2008, 07:13:29 AM »
yes
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Offline Lonestar

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Re: SCH3-
« Reply #4 on: March 03, 2008, 08:01:31 AM »
put simply, SN2 requires the nucleophile to perform a "back side attack" which means it hits the carbon on the side opposite the side bonded to the leaving group, so a primary is good cuase no hinderence to the "back side attack". A tert alkyl halide is bad cuase it'll be all clustered and hindered.

if you got a primary alkyl halide and a strong nucleophile then yeah, most likely SN2 hence, it depends on your alkyl halide

it should be noted that the strength of the nucleophile is not important in an SN1 reaction

Offline azmanam

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Re: SCH3-
« Reply #5 on: March 03, 2008, 08:15:39 AM »
Quote
strength of the nucleophile is not important in an SN1 reaction

unless it is a strong nucleophile AND a strong base, then competing pathways may emerge, depending on the alkyl halide.

now, concentration of nucleophile is not important to the rate of the SN1.  know why?
Knowing why you got a question wrong is better than knowing that you got a question right.

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