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Problem: When styrene (below) is dissolved in a strong Bronsted-Lowry acid (like HCL), it can be protonated on either of the two carbons in the vinyl substituent, to form two isomeric strong electrophiles (carbocations). (Assume the aromatic C=C π bonds are not protonated.)

325_Bronsted-Lowry acid.jpg

a. Draw both possible carbocations, as well as the electron motion by which they are formed from styrene and HCL.

b. Assume the HCL is in aqueous solution, and that there is lots of H2O around. Draw a Lewis acid/base reaction between each of the possible carbocations (strong E+) with water (a weak nucleophile).

c. Follow each lewis acid/base reaction with a simple BL acid/base reaction, with H2O acting as a base to remove a proton and re-form a new neutral organic molecule.

d. Predict which of the two isomeric alcohols you just drew will be formed predominantly under the conditions described above. Why is it formed preferentially? Which step above (a, b or c) determines which alcohol isomer is formed?

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