Name __ SID. Page 1 of 10 1. (10 ps) Complete a balanced equation for the hydrolysis of the stai acid as the reaction conditions. Include stereochemistry. 1g material shown, using excess aqueous strong “hydrolysis using | excess aqueous | strong acid” : (balance equation) 2. (10 pt) ! Complete a balanced equation for the hydrolysis of the starting material shown, using excess aqueous strong ! acid as the reaction conditions. Ignore stereochemistry. “hydrolysis using | excess aqueous! strong acid” :Name SID. Page 2 of 10 Draw a curved arrow mechanism for the following reaction I °. oO EtJN (cat) a ox] TY ——e if 4. (10 pt) | Use labeled structure drawing(s) to explain why the product below is NOT formed in significant quantities as a competing product in the reaction scheme above. | (Note: relevant drawings are required. Text-only answers will earn no credit.) oa is NOT formed as a major competing product in the reaction above because:Name SID. Page 3 of 10 5. (10 pt) Draw a curved arrow mechanism for the following reaction. Ignore stereochemistry. t NaCN (cat,) Ho. OH ; i HON, | ——> oe : i tl } N OH ! Predict all organic products of the following reaction sequence. Include stereoisomers if relevant. i D 1 or (equiv) ! DO" 2. Hj0* workup :Name SID. Page 4 of 10 7. (10 pt) raw a curved arrow mechanism forthe folowing reaction Ignore stereochemistry. 9° i NaOH (cat) 8. (0p) . . raw a curved arrow mechanism for the following reaction. Ignore stereochemistry. HCI (cat.) 9 co, H,0 (solvent) Aron heat RPage 5 of 10 E 2 (10 pt) 9. NaOH (cat) 2 g g 8 3 g & S the structure at the left ‘mechanism: 10. (10 pd) 8 a Draw a curved arrow mechanism for the following reaction.Page 6 of 10 SID. Name 1@) DQ Hq N. oo H N. oo NaBD(CAc}; NaBH(OAc)3 Fill in reaction conditions (1-2 steps per box) and indicate how many stereoisomers of each product would form. Draw the starting materials to complete the two reaction schemes, including an aldehyde or ketone in each. Pay attention to the deuterium locations. Ignore stereochemistry. 12. (10 pt) iow many stereoisomers?Name SID. Page 7 of 10 13. (10 pt) Predict the major organic products of the reaction. Make sure the equation is balanced. Ignore stereochemistry. 1. KH (1 equiv) (tequiv) (1 equiv) 0 (1 equiv) Circle the imine that would be more electrophilic. Explain your choice using labelled structure drawing(s), : (Note: relevant drawings are required. Text-only answers will earn no credit)Name SID. Page 8 of 10 15. (10 pt) (add stereochemistry) 16. (10 pt) ! Draw a curved arrow mechanism for the following reaction. ignore stereochemistry. HCI (cat) ° HOLA 9 ~_0. Noon ee aa ThPage 9 of 10 SID Name 17. (10 pt) Q 2 1g structures in the multistep synthesis scheme. Ignore stereochemistry. Draw a curved arrow mechanism for the following reaction. Add stereochemistry to the products.Name sID. Page 10 of 10 19. Cocaine Biosynthesis (20 pt) Cocaine is isolated from the leaves of Erythoxylum coca (coca plants). Although the exact biosynthetic pathway leading to cocaine has not been fully established, one current hypothesis is that it includes the following enzyme-catalyzed reactions." A. Draw a curved arrow mechanism for the following reaction, using an iminium as the first electrophile e& 9 es 9 9 N nzB (cat.) C3 A scon ON. SCoA HSGan’ (2 equiv) H B. Classify the following reaction, COLL ON: 'SCoA rH C. Draw a curved arrow mechanism for the following reaction. Add stereochemistry (wedged/dashed li he starti re based on the stereochemistry of the prodi : ON ‘SCOA } (add stereochemisiryy