8. Write the mechanism and product of the following reaction. Show the movement of pairs of electrons with curved arrows. Show all intermediates and their charges. CH Step (1) one equiv of NaOCH, in CH;OH solvent Step (2) HCl and water

5. Write a detailed chemical mechanism for the following reaction. [10 pts] NBS hv ? For full credit, • Explicitly label initiation, propagation, and termination steps. • Use 'curly arrows' to denote electron flow. Show all resonance forms of the reaction intermediate(s). N-Br NBS (N-bromosuccinimde) • Show reaction at any resonance forms of the reaction intermediate(s) that lead to different products. including constitutional and stereochemical isomers (if any). Show two different termination steps. Showing more steps will not earn points; wrong steps will lose points

3. Two cyclic products are possible from the Dieckmann condensation shown below, but only one product forms. 1. NaOEt, EtOH EtO OEt 2. H3O+ a. Provide the product of the Dieckmann condensation shown above. b. Provide a complete mechanism, using appropriate curved arrows to show the direction of electron flow, for the Dieckmann condensation. You must show the correct formal charges on atoms at each step. You must write out the full structure of each intermediate using an accepted chemical style. Clearly indicate which steps are reversible or unidirectional with the correct reaction arrows.

4. Write the mechanism of the following reaction. Use curved arrows to show the movement of electrons in each step. Draw the bromonium ion intermediate emphasizing the major position of positive charge. Draw and write "cis" or "trans" of the high priority groups in the product for full credit + Br-OH, water, NaOH Hi CH3