This is not the relevant question to this video but it's related to organic Chemistry. Does LG in alkyl halide affect the mechanism of rxn? I have a alkyl halide molecule with LG, bromide and tosylate. Bromide favours elimination while OTS favours substitution. Is this correct statement?
Yes and no. The LG by itself won’t do much. It really depends on the structure of your molecule. Tosylate is very bulky. It may or may not be relevant. The sigma anti-binding orbital for tosylate and bromide will have different energies. It also may or may not be relevant. So, in short, no, you cannot make a generic statement that bromide favors elimination while a tosylate favors a substitution as there are too many factors to consider in every specific case.
@VictortheOrganicChemistryTutor All the other conditions for both rxn are same. I mean substrate and nucleophile/base are the same. The only difference in the structure of the substrate is the leaving group, and they behave in a way I already mentioned. I'm totally lost.
Ah, I see. What you’re describing is a kinetic effect rooted in the conformations of the compounds. The tosylate is very bulky and will force the molecule into a conformation where the tosylate is anti to another group making elimination kinetically unfavorable. Bromine doesn’t behave in this manner since it’s not bulky at all. This actually gives me an idea for the future video!
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This is not the relevant question to this video but it's related to organic Chemistry. Does LG in alkyl halide affect the mechanism of rxn? I have a alkyl halide molecule with LG, bromide and tosylate. Bromide favours elimination while OTS favours substitution. Is this correct statement?
Yes and no. The LG by itself won’t do much. It really depends on the structure of your molecule. Tosylate is very bulky. It may or may not be relevant. The sigma anti-binding orbital for tosylate and bromide will have different energies. It also may or may not be relevant. So, in short, no, you cannot make a generic statement that bromide favors elimination while a tosylate favors a substitution as there are too many factors to consider in every specific case.
@VictortheOrganicChemistryTutor All the other conditions for both rxn are same. I mean substrate and nucleophile/base are the same. The only difference in the structure of the substrate is the leaving group, and they behave in a way I already mentioned. I'm totally lost.
Ah, I see. What you’re describing is a kinetic effect rooted in the conformations of the compounds. The tosylate is very bulky and will force the molecule into a conformation where the tosylate is anti to another group making elimination kinetically unfavorable. Bromine doesn’t behave in this manner since it’s not bulky at all. This actually gives me an idea for the future video!
@VictortheOrganicChemistryTutor Got the point, thanks a lot. I would love to watch that video.
@@VictortheOrganicChemistryTutor would love to see that video too!