Identify ALL appropriate starting materials and conditions to selectively generate the desired product racemic mixture Br OH H2SO4 A B EtOH NaOEt DMF C 1) Hg(OAc)2, EtOH 1) BH3, THF D 2) NaBH4, NaOH 2) H2O2, NaOEt E 1) BH3, THF 2) H2O2, NaOH 3) NaH 4) EtBr FL 1) H2SO4, EtOH 2) NaH 3) EtBr

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
Problem 27MP
Question
None
Identify ALL appropriate starting materials and conditions to selectively generate the desired product
racemic mixture
Br
OH
H2SO4
A
B
EtOH
NaOEt
DMF
C
1) Hg(OAc)2, EtOH
1) BH3, THF
D
2) NaBH4, NaOH
2) H2O2, NaOEt
E
1) BH3, THF
2) H2O2, NaOH
3) NaH
4) EtBr
FL
1) H2SO4, EtOH
2) NaH
3) EtBr
Transcribed Image Text:Identify ALL appropriate starting materials and conditions to selectively generate the desired product racemic mixture Br OH H2SO4 A B EtOH NaOEt DMF C 1) Hg(OAc)2, EtOH 1) BH3, THF D 2) NaBH4, NaOH 2) H2O2, NaOEt E 1) BH3, THF 2) H2O2, NaOH 3) NaH 4) EtBr FL 1) H2SO4, EtOH 2) NaH 3) EtBr
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