Answer Happy

Part A
Compound A has the formula C9H19Cl. B is a C9H19Br compound. A and B undergo base-promoted E2 elimination to give the same alkene C as the major product as well as different minor products. C reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane. Addition of HCI to C yields A as the major product. Propose structures for A and B. Do not use stereobonds in your answer. ● In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. 99-85 O Sn [F ChemDoodleⓇ

Compounds X has the formula C7H₁5CI; Y is C7H15Br. X undergoes base-promoted E2 elimination to give a single alkene product Z. Y likewise reacts under similar conditions to give a single alkene product that is isomeric with Z Catalytic hydrogenation of Z affords 3-ethylpentane. X readily reacts in SN2 fashion with sodium iodide in acetone. Y does not undergo a similar SN2 reaction. Propose structures for X and Y. . Do not use stereobonds in your answer. . In cases where there is more than one possible structure for each molecule, just give one for each. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. **8 O Sn [F O Sn [F CH₂ CH3 CH3 CH3 -CH3 ChemDoodle +く ChemDoodle