Question

0/1 pts ncorrect Question 1 Select from the list of numbered reagents/conditions the correct order that would yield the desired synthesis indicated below. Enter as your answer the sequence of numbers separated by commas. This synthesis is not intended to be an efficient or elegant approach; rather, it is intended to get you to "revisit" several reactions so that you can become more facile using your mental synthesis toolbox. CH4 9. CH3Br, FeBr3 10. xs NH3 11. SOC2. pyridine 12. PBr3 5. H2. Pt 6. Mg, ether 7. Br2, hu 8. 1) xs LAH 1. NaH 2. fuming H2SO 4. 1) CO2 2)H'(a) 2) H'(ea) 7.6,4,8.2,5

Answer 1

1) CH, Br2 CH,Br Me ether cHjMgBr coCH,CoOH Mg, ether CHBr MS.etner, CH MgBr _CO..Ht CH CoOH xs LAH, H+ CH,CH OH PBr3 NaH CH,CH Br H2, Pt H2C-CH CH3

Therefore,

Ans = 7,6,4,8,12,1,5