Show reagents that can be used to achieve the following transformation: 16-0 A feasible synthetic pathway goes through the ketone shown below: 1st reagents The transformations above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B t-BUOK E H₂, Lindlar's cat 1) LIAH 2) H₂O 2nd O reagents ii conc. H₂SO, heat F H₂ Pt 3 DMP or PCC V C Na₂Cr₂O H₂50 H₂O G Br, hv K 1) MeMgBr: 2) H₂O D Na Me H dilute H₂SO L 1) BH-THF: 2) H₂O₂, NaOH

ο When cyclohexanone is heated in the presence of a large amount of acetone cyanohydrin and a small amount of base, cyclohexanone cyanohydrin and acetone are formed. On a sheet of paper, write a mechanism for this reaction. Then, in the window below, draw the first intermediate in your mechanism. 8. OH H₂C H3C CN HO CN + 0 CH3CCH3 • You do not have to consider stereochemistry. •You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na+, I, in your answer. • In cases where there is more than one answer, just draw one. + √n [] ?

Show the reagents for the conversion below: NH2

Give the necessary reagents in the correct order, as a string of letters.

Propose an efficient synthesis for the following transformation: +-4 The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A t-BuOK E H₂, Lindlar's cat. I 1) LIAIH4; 2) H3O+ B HBr, ROOR F MeMgBr; 2) H3O+ J DMP or PCC C Na2Cr₂O7, H₂SO4, H₂O G TsCl, py K conc. H₂SO4, heat D HBr H dilute H₂SO4 L 1) BH3-THF; 2) H₂O2, NaOH

Propose an efficient synthesis for the following transformation. ند - ما The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B HBr, ROOR D - HBr G HCECNa 1) 03; 2) DMS E H₂, Lindlar's cat. H 1) xs NaNH2, 2) H,O C 1) MeMgBr; 2) H3O+ F H₂SO4, H₂O, HgSO4 I 1) R₂BH; 2) H₂O2, NaOH

Using the reagent list, identify the reagents needed to complete the two-step synthesis below. Enter the code for the reagent into the appropriate box. Step 1 Step 2 CI OC

Give the necessary reagents in the correct order, as a string of letters.