November 17, 2024, 09:30:56 PM
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Topic: am i right in thinking that this is down to steric acceleration...  (Read 1553 times)

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Offline pyrrole

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The question was as follows

 The   hydrolysis  of  bromide  E  occurs  faster  than  the  hydrolysis  of  tert-butyl
bromide C unde r  similar reaction conditions.

(And bromide E was the same but with another tert group at the other end of the molecule. )

As there is a decrease in coordination between starting material and the carbocation intermediate (with loss of leaving group being the rds), the extra bulky substituant will lead to steric acceleration.

However i have a feeling i'm wrong, as steric acceleration is due to the reactants in the ground state being more compressed/strained than the transition state. But here, the extra bulky group is not attached to the carbon containing the leaving group, it is attached to the carbon next to it. Though i cant think of any other explanation

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