Stereochemistry of Alkene Additions Worksheet

Stereochemistry of Alkene Additions

Carefully read each question and provide comprehensive answers. Show all your work for mechanisms and stereochemical predictions. Use appropriate chemical structures and nomenclature.

1. Which of the following reactions typically proceeds with anti-addition?

2. Syn-addition refers to the addition of two substituents to the same face of the alkene. Which of the following reagents typically undergoes syn-addition?

3. The addition of HBr to an alkene typically follows  's rule, leading to the more substituted product.

4. Hydroxylation of alkenes using KMnO4 (cold, dilute) results in a  -addition of two hydroxyl groups.

5. Draw the major product(s) for the reaction of cis-2-butene with Br2. Clearly indicate the stereochemistry (e.g., using wedges and dashes).

6. Explain why the hydroboration-oxidation of an alkene results in a syn-addition of H and OH.

7. The addition of H2 with a metal catalyst (e.g., Pd/C) to an alkene is a stereospecific anti-addition.

8. Ozonolysis followed by reductive workup (e.g., Zn/H2O) can be used to determine the position of the double bond in an alkene.

9. Propose a detailed reaction mechanism, including all intermediates and transition states, for the bromination of cyclohexene. Clearly show why the reaction yields a trans-dibromide product.