Questions:
1. Give the major product.
2. What is the product in the dihydroxylation of (Z)-3-hexene?
3. What is the product in the dihydroxylation of (E)-3-hexene?
4. Draw the intermediate of this reaction.
5. Fill in the missing reactants, reagents, and product.
Solutions
1. A syn-1,2-ethanediol is formed. There is no stereocenter in this particular reaction. The OH groups are on the same side.
2. Meso-3,4-hexanediol is formed. There are 2 stereocenters in this reaction.
3. A racemic mixture of 3,4-hexanediol is formed. There are 2 stereocenters in both products.
4. A cyclic osmic ester is formed.
5. The Diels-Alder cycloaddition reaction is needed in the first box to form the cyclohexene. The second box needs a reagent to reduce the intermediate cyclic ester. The third box has the product: 1,2-cyclohexanediol.
