Which of the following reaciton sequences will produce the diol shown in the highest yield? (A) РСС 1) xs CH3M9B NaBH4 OH но H. CH2CI2 2) H20 CH3OH HO NABH4 TMSCI 1) xs CH3M9B OH OCH3 CH3OH EtN 2) H30* HO OH TMSCI 1) xs CH3MGB TBAF (C) HO HO Et3N 2) H20 OH 1) LIAIH4 1) xs CH3MgBr (D) OCH3 HO 2) H20 2) H30*

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations
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Problem 40AP: The following Walden cycle has been carried out. Explain the results, and indicate where Walden...
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The answer is C, but I need help with the explanation. Why is c?
Which of the following reaciton sequences will produce the diol
shown in the highest yield?
(A)
PCC
1) xs CH3MGB
NABH4
OH
но
H.
CH2CI2
2) H20
CH3OH
но
(B)
H.
NaBH4
TMSCI
1) xs CH3M9B
OH
OCH3
CH3OH
Et3N
2) H,O*
но
OH
TMSCI
1) xs CH3MGB TBAF
(C)
HO
H.
HO
Et3N
2) H20
OH
1) LIAIH,
1) xs CH3MgBr
(D)
OCH3
HO
2) H20
2) H30*
Transcribed Image Text:Which of the following reaciton sequences will produce the diol shown in the highest yield? (A) PCC 1) xs CH3MGB NABH4 OH но H. CH2CI2 2) H20 CH3OH но (B) H. NaBH4 TMSCI 1) xs CH3M9B OH OCH3 CH3OH Et3N 2) H,O* но OH TMSCI 1) xs CH3MGB TBAF (C) HO H. HO Et3N 2) H20 OH 1) LIAIH, 1) xs CH3MgBr (D) OCH3 HO 2) H20 2) H30*
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