H;C CH3 HBr H;C H 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. ®, H: ExP CONT. H C N

Draw a structural formula for the product of this Diels-Alder reaction, including all stereoisomers of the product. &.I- CHO ● CHO • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If a group is achiral, do not use wedged or hashed bonds on it. • 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.

Noting the curved anows, draw all the product(s), organic and inorganic, of the following reaction. H3C ed H CHS • You do not have to consider stereochemistry. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right comer. Separate structures with+signs from the drop-dowa menu

The following statements (parts a-e) describe a specific reaction along with its regio- and/or stereo-control. Match the reaction conditions below (1-8) that correctly corresponds to the statement. Answer with 1, 2, 3, 4, 5, 6, 7, or 8. H₂ 1. Hg(OAc)2, H₂O 1. BH3, THF H₂ Lindlar's cat. Pd/C 2. NaBH4 2. H₂O₂, H₂O, OH- Condition 4 Condition 1 Condition 2 Condition 3 H₂O+ HBr NaNH, HBr H₂O2 Condition 7 Condition 8 Condition 6 Condition 5 a. Reaction condition for the reduction of an alkyne to a cis-alkene. b. Markovnikov addition of water to a double bond, with no carbocation rearrangement. c. Anti-Markovnikov addition of HBr to a double bond. d. Anti-Markovnikov addition of water to a double bond. e Reaction condition to change 1,2-dimethylcyclohexene into cis-1,2-dimethylcyclohexane.