7. CH3CH2OH + PCC → (i) 8. 2-bromobutane + Mg (in anhydrous ether) → (j)

H H ČH3 Br р. + CH;C=C: in acetone Reaction Type(s) Mechanism(s) Product(s). Stereochemistry (if applicable) q. p-chloronitrobenzene + sodium ethoxide Reaction Type(s) Mechanism(s) Product(s). Stereochemistry (if applicable)

Part 1) Identify the stereochemistry of the three double bonds (A, B, and C) in the structure as E, Z or no stereochemistry. Part 2) Identify the number of substituents associated with each double bond (A, B, and C). A Stereochemistry of double bond A: [Select] [Select] E Number of Substituents on double Z No stereochemistry Stereochemistry of double bond B: [Select] Number of Substituents on double bond B: [Select] Stereochemistry of double bond C: [Select] Number of Substituents on double bond C: [Select] C

Draw the major organic product(s) of the following reaction. CH3 H₂C-C-C=C-H CH3 + • You do not have to consider stereochemistry. • Separate multiple products using the + sign from the drop-down menu. • If no reaction occurs, draw the organic starting material. MELL ? Ⓡ NaNH, / NH3(I) ChemDoodle Br +