Draw the major product(s) of the following reactions including stereochemistry when it is appropriate. CH₂CH₂-CEC-CH₂CH₂ + 1 Br₂ . Consider E/Z stereochemistry of alkenes. • If there is more than one major product possible, draw all of them. • 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. ● i

Draw the product(s) of the following reactions. H₂ Lindlar catalyst CH3CH₂-CEC-CH₂CH3 • Consider E/Z stereochemistry of alkenes. ● If no reaction occurs, draw the organic starting material. • 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.

Draw the predominant product(s) of the following reactions including stereochemistry when it is appropriate. 2 HBr CH3-CEC-CH3 + • Consider E/Z stereochemistry of alkenes. • Do not show stereochemistry in other cases. If no reaction occurs, draw the organic starting material. • 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. WP ***** ? ChemDoodleⓇ n [F < 56

d Draw the major product(s) of the following reactions including stereochemistry when it is appropriate. CH₂CH₂-CEC-CH3 + 1 Cl₂ • Consider E/Z stereochemistry of alkenes. • If there is more than one major product possible, draw all of them. • 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. ●