Problem 60 IR Spectrum (liquid film) 4000 3000 2000 1600 1200 800 V (cm") 100- UV Spectrum 105 Mass Spectrum 80 A max 270 nm (log,ɛ 2.6) M*- 120 solvent: methanol C9H12 40 80 120 160 200 240 280 m/e 13C NMR Spectrum (100.0 MHz, CDCI, solution) expansion 135 130 ppm DEPT CH CH,t CHt 24 20 ppm еxpansion expansion proton decoupled solvent 135 130 ppm 24 20 ppm 200 160 120 80 40 0 8 (ppm) 1H NMR Spectrum (400 MHz, CDCI, solution) resolves into 2 peaks at higher field вхpansion еxpansion TMS 6.8 6.6 ppm 2.2 2.0 ppm 10 8 7 6 4 3 2 1 8 (ppm) 149 % of base peak

Draw the curved arrow mechanism for the reaction between (2R,3S)-3,5-dimethylhexan-2-ol and PCl3. Note the specific instructions for each box. Include nonzero formal charges and lone pairs of electrons on all appropriate atoms. Then answer the question about the mechanism.

Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic steps. Be sure to account for all bond-breaking and bond-making steps. Drawing Arrows H•• H₂O H :O: H Na Ⓒ H H :0: H H-8:0 :O: I :O: H Na + Drag To Pan

Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic steps. Be sure to account for all bond-breaking and bond-making steps. Drawing Arrows dilute NaOH DMSO + :Br: Undo Reset Done Na+ H Drag To Pan