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Topic: Nucleophilic Substitution  (Read 2403 times)

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Offline Hanlon

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Nucleophilic Substitution
« on: November 29, 2010, 08:30:06 PM »
So I got this question:

Nucleophilic substitutions can be subject to solvent effects.

Based on your results, did you observe a solvent effect in this experiment?
(In the second part, choose the appropriate reason for your conclusion.)

based on Gas Chromography I have 25% 2-chlorobutane and 75% 2-bromobutane made from 2-butanol in a substitution reaction.

my nucleophilic medium contains 100g ice, 76ml conc. H2SO4, 19.0g NH4Cl and 35g NH4Br

based on the fact that I got more 2-bromobutane then 2-chlorobutane am I correct to assume that there was "no solvent effect" because:

H2SO4 is a polar protic solvent, which will cause hydrogen bonding around the reactant compound therefore inversing the relationship between nucleophilicity and basicity. However, Br- being a weaker base and thus a better nucleophile still created more product then Cl- being the worse of the two nucleophiles, then there was no solvent effect in this experiement.

And am I also right to assume that this is a SN1 reaction, because SN1 reactions favor protic solvents?

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