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Topic: in SN2 E2, acetate ion is base or nucleophile? -SCH3?  (Read 17647 times)

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Offline kims

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in SN2 E2, acetate ion is base or nucleophile? -SCH3?
« on: November 30, 2007, 05:52:32 PM »
There is a 2-iodopentane. Two separate reactions there is acetate ion and -SCH3. Will these go SN2 or E2?
The acetate ion is not a strong base, but will steric hindrance cause it to do mostly elimination?
The -SCH3 is not weak but it's not a strong base, correct? Actually I don't know anything about this molecule. Can someone tell me if it is strong or weak relative to other molecules.

Offline ultrashogun

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Re: in SN2 E2, acetate ion is base or nucleophile? -SCH3?
« Reply #1 on: November 30, 2007, 08:48:11 PM »
Im pretty sure that -SCH3 will do Sn2 because it is a soft nucleophile. Its lower in the periodic table and so its HOMO is larger and more spread out, this is important because orbital overlap plays a large role in Sn2, the electrophile not being charged.

Im pretty sure that acetate is not a strong enough base for E2. Are you sure that it cant be an Sn1 or E1 reaction?

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