Which of the following synthetic sequences would not accomplish the transformation shown? OH of H-B TSCI NaCECH 1) (A) pyridine 2) H2O2, NAOH 1) TSCI pyridine PBr3 Mg° 1) H. 1) ВНз-THF PCC Et,0 2) H20 2) (BUOK 2) H2O2, NAOH BrMg 1) TSCI 1) DMSO, (COCI)2 1) pyridine 1) H2, Pt Dess-Martin Periodinane (C) 2) NET3 2) H20 2) (BUOK 2) H30* CH2CI2 SOCI2 NaCECH H2 1) O3 (D) pyridine Lindlar's cat. 2) Me2S

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
Section21.SE: Something Extra
Problem 35MP
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Which of the following synthetic sequences would not accomplish the
transformation shown?
OH
H-B
TSCI
NACECH
1)
(A)
pyridine
2) H202, NaOH
1) TSCI
(B)
PBR3
Mg°
1)
H.
pyridine
1) BH3-THF
РСС
Et,0
2) H20
2) (BUOK
2) H2O2, NaOH
BrMg.
1) TSCI
pyridine
1) DMSO, (COCI)2 1)
1) H2, Pt
Dess-Martin Periodinane
(C)
2) NET3
2) H20
2) (BUOK
2) H3O*
CH2Cl2
SOCI2
H2
1) O3
NaCECH
(D)
pyridine
Lindlar's cat.
2) Me2S
Transcribed Image Text:Which of the following synthetic sequences would not accomplish the transformation shown? OH H-B TSCI NACECH 1) (A) pyridine 2) H202, NaOH 1) TSCI (B) PBR3 Mg° 1) H. pyridine 1) BH3-THF РСС Et,0 2) H20 2) (BUOK 2) H2O2, NaOH BrMg. 1) TSCI pyridine 1) DMSO, (COCI)2 1) 1) H2, Pt Dess-Martin Periodinane (C) 2) NET3 2) H20 2) (BUOK 2) H3O* CH2Cl2 SOCI2 H2 1) O3 NaCECH (D) pyridine Lindlar's cat. 2) Me2S
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