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Notes: A ‘detailed’ mechanism should illustrate all intermediates, by-products, and electron-pushing arrows. The marking scheme is...

Notes: A ‘detailed’ mechanism should illustrate all intermediates, by-products, and electron-pushing arrows. The marking scheme is given for each question as a guide; It is subject to minor changes.

In class, we learned how to synthesize epoxides from alkenes using meta-chloroperbenzoic acid (mCPBA). Epoxides, like bromonium ions and mercuronium ions, can be ring-opened with various nucleophiles. The stereochemistry of the product depends on if the ring-opening occurs under acidic or basic conditions. The following two reactions – ring opening of an epoxide with water – illustrate this effect. Explain why the outcome of the reaction changes under these two conditions and provide electron-pushing arrows to explain the mechanisms. The following websites may be useful:

https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/

https://www.masterorganicchemistry.com/2015/02/02/opening-of-epoxides-with-acid/

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