The following is the predicted 'H-NMR spectrum for an unknown compound with molecular formula CgH40. This compound is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. 5 6H 2H 4H 1H 1H Choose from the constitutional isomers below t assign a structure to this spectrum. CH3 CH3 CH2CH3 CH;CH;CH,CHCH,OH CH;CH,CHCH,OH CH,CH2CHCHCH, b| d a a b c d eg a b c d ÓH f B (Choose the letter corresponding to the correct structure from the drop-down list provided.) Correet Structure: V Assign signal number 5 (indicated as a red number on the spectrum above) to the corresponding hydrogen(s) (shown as a red lower-case letter on the structure above). If relevant, consider the possibility of diastereotopic hydrogens with slightly different chemical shifts. (Write the letter(s) of the hydrogen (or set of equivalent hydrogens) in the box provided. If the signal arises from more than one set of hydrogens on the structure above, write both letters in alphabetical order, e.g., ab) Signal number 5 corresponds to hydrogen(s):

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
Chapter13: Nuclear Magnetic Resonance Spectroscopy
Section13.7: Chemical Shift
Problem 13.5P: Following are two constitutional isomers with the molecular formula C4H8O2. (a) Predict the number...
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The following is the predicted H-NMR spectrum for an unknown compound with molecular formula C6H140. This compound is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas.
5
6H
2
2H
4H
1H
1H
PPM
Choose from the constitutional isomers below to assign a structure to this spectrum.
e
f
b a
CH3
CH2CH3
CH3
CH;CH,CH,CHCH,OH CH,CH,CHCH,OH CH;CH,CHCHCH,
b| d
CH3CH2CH2CHCH2OH CH3CH2ČHCH2OH
a b c deg
a
a b c de
OH f
А
B
C
(Choose the letter corresponding to the correct structure from the drop-down list provided.)
Correct Structure:
Assign signal number 5 (indicated as a red number on the spectrum above) to the corresponding hydrogen(s) (shown as a red lower-case letter on the structure above). If relevant, consider the possibility of diastereotopic hydrogens with slightly different chemical shifts.
(Write the letter(s) of the hydrogen (or set of equivalent hydrogens) in the box provided. If the signal arises from more than one set of hydrogens on the structure above, write both letters in alphabetical order, e.g., ab)
Signal number 5 corresponds to hydrogen(s):
Transcribed Image Text:The following is the predicted H-NMR spectrum for an unknown compound with molecular formula C6H140. This compound is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. 5 6H 2 2H 4H 1H 1H PPM Choose from the constitutional isomers below to assign a structure to this spectrum. e f b a CH3 CH2CH3 CH3 CH;CH,CH,CHCH,OH CH,CH,CHCH,OH CH;CH,CHCHCH, b| d CH3CH2CH2CHCH2OH CH3CH2ČHCH2OH a b c deg a a b c de OH f А B C (Choose the letter corresponding to the correct structure from the drop-down list provided.) Correct Structure: Assign signal number 5 (indicated as a red number on the spectrum above) to the corresponding hydrogen(s) (shown as a red lower-case letter on the structure above). If relevant, consider the possibility of diastereotopic hydrogens with slightly different chemical shifts. (Write the letter(s) of the hydrogen (or set of equivalent hydrogens) in the box provided. If the signal arises from more than one set of hydrogens on the structure above, write both letters in alphabetical order, e.g., ab) Signal number 5 corresponds to hydrogen(s):
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