A student was attempting the reaction outlined below. The isolated product was analyzed by MS and 1H NMR spectroscopy. Although the MS spectrum matches well, the 1H NMR spectrum does not match the intended product. Determine the structure of the product obtained and explain why it is preferred. Assign all 1H NMR signals to specific chemical environments or specific hydrogens in your structure, show your reasoning on the spectrum. OH но PCC, CH,Cl2 CH;MgBr G 'H•NMR Spectrum of Actual·Product 3H H 3H E F IH IH C IH IH IH IH 2 6 PPM 4.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL4: Proton (1h) Nmr Spectroscopy
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A student was attempting the reaction outlined below. The isolated product was analyzed by MS and 1H NMR
spectroscopy. Although the MS spectrum matches well, the 1H NMR spectrum does not match the intended
product. Determine the structure of the product obtained and explain why it is preferred. Assign all 1H NMR
signals to specific chemical environments or specific hydrogens in your structure, show your reasoning on the
spectrum.
HO
PCC, CH,Cl2
CH;MgBr
'H NMR Spectrum of Actual·Product
3H
H
3H
A
C
D
E F
1H
IH
1H
IH
IH IH
3
0.
4
PPM
6.
5.
2.
Transcribed Image Text:A student was attempting the reaction outlined below. The isolated product was analyzed by MS and 1H NMR spectroscopy. Although the MS spectrum matches well, the 1H NMR spectrum does not match the intended product. Determine the structure of the product obtained and explain why it is preferred. Assign all 1H NMR signals to specific chemical environments or specific hydrogens in your structure, show your reasoning on the spectrum. HO PCC, CH,Cl2 CH;MgBr 'H NMR Spectrum of Actual·Product 3H H 3H A C D E F 1H IH 1H IH IH IH 3 0. 4 PPM 6. 5. 2.
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