Question

Consider the reaction below. Note that the stereochemistry of the product is now shown: 12 points. 5. Br2 CH2Cl2 Br Br a. Draw the most stable chair conformation of the starting material (i.e. the alkene). Use the chair template provided on your answer sheet. You do not need to draw ring hydrogens. (2 points) b. Draw a detailed stepwise mechanism for the reaction. Draw all intermediates and use curved arrows to show 'electron movement'. If multiple stereoisomers of the same intermediate are formed, you may simply draw one. Use chair conformations in your mechanism. (8 points) c. Draw the line-angle formula (not chair conformation) of the major product of the reaction with proper stereochemistry. There is only one major product. (2 points) 6. Propose a synthesis for the target shown below. You must start your synthetic route using the compound shown; from there, you can use any other materials/reagents you need. Show all reagents/conditions that you would use in each step. Draw out all synthetic Intermediatos that are stable enough to be isolated (no cations, anions or radicals). No mechanisms: 9 points. Он steps Он (meso)

Answer 1

н а. _Br H b. "Br Br Овг Br Br он но он, Н.) Н 1. OsO4 NaNH2 H2, Lindlar cat. ОН 2. NaHSO3, H20 - Br (3R,4S)-hexane-3,4-diol (3R,4S)-hexane-3,4-diol Cis alkene Alkylation