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a) There are several reagents that can be used to effect addition to a double bo

ID: 924569 • Letter: A

Question

a) There are several reagents that can be used to effect addition to a double bond including: acid and water, oxymercuration–demercuration reagents, and hydroboration–oxidation reagents. Inspect the final product and select all the reasons why acid in water was chosen to effect the following transformation instead of the other reagents.

b) Complete the mechanism for the reaction by adding any missing atoms, bonds, charges, nonbonding electrons, and curved arrows. The reagents chosen for the transformation are: H3O , H2O.

Explanation / Answer

a) The correct answers are

---Hydroboration oxidation reagent yields the anti-Markovnikov product of addition

In this reaction the OH groups gets attached to the less substituted carbon unlike oxymercuration-demercuration or addition of acid/ water

---The addition with acid and water as reagents allow sigmatropic rearragement

---Oxymercuration-demercuration reagnets prevent sigmatropic rearragement

--the reaction requires markovnikov's product without sigmatropic rearregement