Question 8 (Spectroscopic Analysis): Our Laboratory Facilitator, Nick, decides to try his hand at some organic chemistry. He performs the following hydration reaction, which, in theory, can produce two distinct isomeric products (A and B). H₂O H₂SO4 OH Тон A B When the reaction is complete, he notices as per TLC analysis that in fact two products were formed. He decides to isolate one of them, and characterize it. He acquires the following ¹HNMR spectrum (data tabulated below). + ...

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
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.43P: The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas...
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Which molecule has Nick isolated, A or B? Why? A Nick has isolated molecule A since there are 5 distinct signals observed. Molecule B would produce 4 distinct signals. B Nick has isolated molecule B because there are 5 distinct signals observed. Molecule A would produce 6 distinct signals. C) Nick has isolated molecule B since this is likely the major product of this reaction. A D Nick has isolated molecule A since it is likely the major product of this reaction. E) Nick has isolated a mixture of products (A and B)
5
Chemical Shift (ppm)
4.81
3.49
1.96
1.19
0.98
3
Splitting/Multiplicity
singlet (s, broad)
quintet (q)
multiplet (m)
PPM
doublet (d)
doublet (d)
-~
2
Integration
1H
1H
1H
3H
6H
Transcribed Image Text:5 Chemical Shift (ppm) 4.81 3.49 1.96 1.19 0.98 3 Splitting/Multiplicity singlet (s, broad) quintet (q) multiplet (m) PPM doublet (d) doublet (d) -~ 2 Integration 1H 1H 1H 3H 6H
Question 8 (Spectroscopic Analysis): Our Laboratory Facilitator, Nick, decides to try his hand at some
organic chemistry. He performs the following hydration reaction, which, in theory, can produce two distinct
isomeric products (A and B).
OH
H₂O
H₂SO4
Тон
A
B
When the reaction is complete, he notices as per TLC analysis that in fact two products were formed. He
decides to isolate one of them, and characterize it. He acquires the following ¹HNMR spectrum (data
tabulated below).
Transcribed Image Text:Question 8 (Spectroscopic Analysis): Our Laboratory Facilitator, Nick, decides to try his hand at some organic chemistry. He performs the following hydration reaction, which, in theory, can produce two distinct isomeric products (A and B). OH H₂O H₂SO4 Тон A B When the reaction is complete, he notices as per TLC analysis that in fact two products were formed. He decides to isolate one of them, and characterize it. He acquires the following ¹HNMR spectrum (data tabulated below).
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