n-Pro Pro H3C Ho CHH n-Pro Pro

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL3: Carbon (13c) Nmr Spectroscopy
Section: Chapter Questions
Problem 8CTQ
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which is the correct reaction?

H3C
H3C
n-Pro
Pro
H3C CH3
OH
H3C
n-Pro
Pro
H3C OPr
OH
n-Pro
(±)
H;C
H3C OPr
OH
n-PrOH
H*
H3C
H3C OH
OPr
n-Pro
(±)
Transcribed Image Text:H3C H3C n-Pro Pro H3C CH3 OH H3C n-Pro Pro H3C OPr OH n-Pro (±) H;C H3C OPr OH n-PrOH H* H3C H3C OH OPr n-Pro (±)
Expert Solution
Step 1

Given reaction is the reaction of nucleophilic ring opening of the epoxide ring. In the case of unsymmetrical epoxide, ring opening takes place in the presence of acidic and basic condition. In the case of basic conditions the nucleophile will attack at the less substituted site of an epoxide whereas in the presence of an acid the nucleophile attack at the more substituted site of an epoxide.

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