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QUESTION 8 10 points Save Answer Using the list, propose the forward synthesis of the retrosynthesis shown below (any number of steps can be used, so long as they get to the desired product in as high a regioselectivity as possible). Please report your answer by typing the letters/symbols sequentially. НО. OH A. CUCI, 0 °C B. CuBr, 0 °C C. Cu20, Cu(NO3)2, H20,0 °C D. CuCN, 0 °C E. SO3, H2SO4, 100 °C F. Cl2, FeCl3, THF, 65 °C G. Br2, FeBr3, THF, 65 °C H. ACCI, AICI3, THF, 65 °C I. H2, Pd/C, EtOH, 25 °C J. KMnO4, H20, 100 °C K. CrO3, H2SO4, Acetone, 0 °C L. NaOH, H2O, 100 °C M. H20, Dilute H2SO4, 100°C N. HNO3, H2SO4, 60 °C O. NaNO2, H2SO4, 0 °C P. mCPBA, DCM, 25 °C Q. KCN, MeCN, 50 °C R. H2NBn, 150 °C S. SOCl2, 75 °C T. LIAIH4, THF, 0 °C U. PBr3, 50 °C V. NaBH4, EtOH, 25 °C W. NaOH, ETOH, 100 °C X. H2SO4, H20, 100°C Y. HBr, EtOH, 50 °C Z. NaNO2, H2SO4, 0 °C !. H2NBn, Et3N, DCM, 40 °C #. Mg, cat. 12, Et20, 35 °C $. EtOH, 25 °C %. NaOH, ETOH, 78 °C ^. CO2, Et20, 25 °C &. TsCI, EtzN, DCM, 25 °C * KOtBu, HOtBu, 50 °C Arial 3 (12pt) T TT TT Paragraph % La T T fx Mashups HTML CSS

Answer 1

Step1. we need to oxidise cyclohexanone to cyclic ester. This reaction is known as Bayer-Villiger Reaction. For this reaction we need a peracid. mCPBA (meta chloro perbenzoic acid) is a very good reagent for this reaction. Mechanism is shown below.

Step2. Now we need to hydrolyze this ester. Hydrolysis in presence of both base and acid at high temperature can be done. Here NaOH is choosen for mild condition.

So the reagents are:

1. P. mCPBA, DCM, $25^{\circ}C$
2. L. NaOH, H2O,
   100°C
   

С-o P. TCPBA, DCM, 25°С L. NaOH, H2O, 100°C НО. ОН H Н. дгай СІ CI СІ + НО Na* ОН . , ОН Н. CI нон сон : НО. ОН