OH

CI Br CI CH3 agua 50°C ácido acético 25°C CH3 SNa DMSO

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correet 1UPAC hame! SH

-NH2 но NH b. OH

Hg(OAc)2 NaBH4, HO¯ TsCl, pyridine KCN CN CN (a) (b) CN OTs (b) (a) 2017 6-01-200 17C Haze AD 0 NG 1 rch hp

OTS OTS OTS OH NaOEt NaCN EtOH NaCN Hexan H₂SO4

ZIR H R H₂ ZIRA N H OH H₂O H+ H₂O

The reaction below requires several mechanistic steps. Six different intermediates are shown below...some are involved in the mechanism and some are not. Your job is to pick the correct intermediates and put them in the correct order. Your answer should be formatted using the number of the first intermediate, followed by the number of the second intermediate, followed by the number of the third intermediate, etc., until you have selected the correct intermediates and placed them in the correct order for the mechanism. An example of the correct answer format would be 231 if you thought intermediate #2 should come first, followed by intermediate #3, and then lastly, intermediate #1. Again, not all of the intermediates are included in this mechanism, so it might be a good idea to try to work it out first on your scratch paper. Do not add any spaces in your answer. 8 4 HO "20 96 5 ***** HCI CH₂Cl₂ (solvent) 1 !! 6 8 hp 7 2

NaOCH 3 CH3OH (H* workup) OHO HO-1-8 NO NO