What routes would successfully complete the transformation shown? OH I. II. OH SOCI₂ [H*], MeOH -H₂O Et₂CuLi O I. and II. O I. and III. O II. and III. O I., II., and III. 1) DIBAL-H 2) H2₂O SOCI₂ 1) Li(O'Bu)3H 2) H₂O NaBH4 H₂O 1) EtMgBr 2) H₂O 1) EtMgBr 2) H₂O

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 5E
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What routes would successfully complete the transformation shown?
OH
I.
II.
OH
SOCI₂
[H*], MeOH
-H₂O
Et₂CuLi
O I. and II.
O I. and III.
O II. and III.
O I., II., and III.
1) DIBAL-H
2) H2₂O
SOCI₂ 1) Li(O'Bu)3H
2) H₂O
NaBH4
H₂O
1) EtMgBr
2) H₂O
1) EtMgBr
2) H₂O
Transcribed Image Text:What routes would successfully complete the transformation shown? OH I. II. OH SOCI₂ [H*], MeOH -H₂O Et₂CuLi O I. and II. O I. and III. O II. and III. O I., II., and III. 1) DIBAL-H 2) H2₂O SOCI₂ 1) Li(O'Bu)3H 2) H₂O NaBH4 H₂O 1) EtMgBr 2) H₂O 1) EtMgBr 2) H₂O
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