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When a dilute solution of acetaldehyde in D2O containing NaOD is shaken, explain why the methyl hydrogens are exchanged with deuterium but the hydrogen attached to the carbonyl carbon is not.

Draw the product formed when the structure shown below undergoes substitution with OH. Interactive 3D display mode ÇH, H Brl Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. Show the appropriate stereochemistry by choosing the dashed or wedged buttons and then clicking a bond on the canvas. O O ® H: EXP. -(7)- %3D H. C

1. +. F5 F7 F8 F10 F11 F12 Insert & ) ( 7. 6 8. Draw the detailed mechanisms for the following transformations. OCH3 H3C 0CH 3 (1.5 equiv) then reflux, 5h 56% CH3 CICH,CH,CI, hv 19.5h N2 N. HO

Draw the structure of the final product(s) of this series of reactions. 1. 1 equivalent of NaNH2 2. CH3CH,CH,CH,Br 3. H2, Lindlar's catalyst 4. Br2 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. • If a group is achiral, do not use wedged or hashed bonds on it. • Draw organic species only. • Do not include lone pairs in your answer. They will not be considered in the grading. • If the reaction produces a racemic mixture, draw both stereoisomers. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu. C opy aste ChemDoodle®