The following two isomeric ketones were among the 68 compounds isolated from the steam-distilled volatile oil of fresh and air-dried marijuana buds (J. Nat. Prod. 1996, 59, 49–51). Propose a separate synthesis for each of these two compounds using only disubstituted alkenes containing four carbon atoms as starting materials. Of the following, which represents a logical retrosynthesis for target molecule A?LoонMgBrMgBrOHOHMgBrOH`MgBr Devise a synthesis of ketone B, starting with the disubstituted alkene shown:вThe transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessaryreagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than onecorrect solution, provide just one answer.АBDMP or PCCNBS, hv2) H30* workupDEFt-BUOKHBr, ROORNa,Cr207, H2SO4, H2OGHMgTSCI, pyHBr

Answered: Of the following, which represents a…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter9: Alkynes: An Introduction To Organic Synthesis

Section9.SE: Something Extra

Problem 21MP

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The following two isomeric ketones were among the 68 compounds isolated from the steam-distilled volatile oil of fresh and air-dried marijuana buds (J. Nat. Prod. 1996, 59, 49–51). Propose a separate synthesis for each of these two compounds using only disubstituted alkenes containing four carbon atoms as starting materials.

Of the following, which represents a logical retrosynthesis for target molecule A?
Lo
он
MgBr
MgBr
OH
OH
MgBr
OH
`MgBr

Devise a synthesis of ketone B, starting with the disubstituted alkene shown:
в
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.
А
B
DMP or PCC
NBS, hv
2) H30* workup
D
E
F
t-BUOK
HBr, ROOR
Na,Cr207, H2SO4, H2O
G
H
Mg
TSCI, py
HBr

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