Which of the following reaction sequences would convert 2- butanol into the deuterated compound below? CH;CH,CHCH3 он H;SO4 (1) BD3/THF A) heat (2) H202, NaOH Он H;SO4 D2/Pt B) heat он PBR3 (1) Mg, diethyl ether C) (2) D20 Он PBR3 N2OD, D20 D) A D B. C.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.68P
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Which of the following reaction sequences would convert 2-
butanol into the deuterated compound below?
CH;CH,CHCH3
он
H;SO4
(1) BD3/THF
A)
heat
(2) H202, NaOH
Он
H;SO4
D2/Pt
B)
heat
он
PBR3
(1) Mg, diethyl ether
C)
(2) D20
Он
PBR3
N2OD, D20
D)
A
D
B.
C.
Transcribed Image Text:Which of the following reaction sequences would convert 2- butanol into the deuterated compound below? CH;CH,CHCH3 он H;SO4 (1) BD3/THF A) heat (2) H202, NaOH Он H;SO4 D2/Pt B) heat он PBR3 (1) Mg, diethyl ether C) (2) D20 Он PBR3 N2OD, D20 D) A D B. C.
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