Sunday, July 29, 2018

organic chemistry - How to explain the selectivity between methanol and methanethiol in an SN1 reaction with an halogenated hydrocarbon?



Consider the SN1 reaction shown below:


https://imgur.com/a/EuMnG


Would different products be formed if $\ce{CH3SH}$ was an additional reagent?


https://imgur.com/a/BCBM9


Superimpose both energy diagrams on top of each other.



For the first question, yes, two products would be formed. I'm confused about the second question though. I know The rate determining step would remain unchanged, as the rate depends on the concentration of the substrate not the nucleophile (SN1 is unimolecular). However, methanethiol is a better nucleophile than methanol. Would the activation energy for the second transition state be less for methanethiol?





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periodic trends - Comparing radii in lithium, beryllium, magnesium, aluminium and sodium ions

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