OH OAc HOʻ excess Ac,0 AcO HO -OH pyridine, 0°C AcO- OAc OH OAc Compound 4 Compound 3 HBr OCH3 OAc OAc AcO AcO AcO- AcO- OAc OAc Compound 6 Compound 5 Br NaOH, H,O OCH3 OH HO Но Compound 7 iii. Propose a detailed reaction mechanism for the conversion of compound 5 to compound 6 and concisely explain the stereochemical outcome.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
Section24.SE: Something Extra
Problem 84AP
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ie qu
tmat
OH
OAc
excess Ac,0
HO
AcO'
НО
он
pyridine, 0°C
AcO
OAc
`OH
OAc
Compound 3
Compound 4
HBr
OCH3
OAc
OAc
?
AcO
AcO
AcO-
AcO
OAc
OAc
Compound 6
Compound 5
Br
NaOH, H2O
OCH3
OH
HO
HO-
Но
Compound 7
iii.
Propose a detailed reaction mechanism for the conversion of compound 5 to
compound 6 and concisely explain the stereochemical outcome.
Transcribed Image Text:ie qu tmat OH OAc excess Ac,0 HO AcO' НО он pyridine, 0°C AcO OAc `OH OAc Compound 3 Compound 4 HBr OCH3 OAc OAc ? AcO AcO AcO- AcO OAc OAc Compound 6 Compound 5 Br NaOH, H2O OCH3 OH HO HO- Но Compound 7 iii. Propose a detailed reaction mechanism for the conversion of compound 5 to compound 6 and concisely explain the stereochemical outcome.
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