The following is the predicted 'H-NMR spectrum for an unknown compound with molecular formula CH140. This compound is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. 3H Hint: this signal is a pair of overlapping 2H multiplets 1 3H 2H 1H 1H PPM Choose from the constitutional isomers below to assign a structure to this spectrum. f CH3 CH2CH3 CH3 CH3CH2CHCHCH3 CH;CH,CHCH2OH CH3CH2CH2CHCH2OH a b c de a a b c deg OH f

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
Section13.8: More Complex Spin–spin Splitting Patterns
Problem 15P: 3-Bromo-1-phenyl-1-propene shows a complex NMR spectrum in which the vinylic proton at C2 is coupled...
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Choose from the constitutional isomers below to assign a structure to this spectrum.
b
a
f
CH3
CH2CH3
CH3
CH3CH2CHCHCH3
b| d
OH f
CH3CH2CHCH2OH
b c d e
CH3CH2CH2CHCH2OH
а b c d e g
a
a
A
B
C
(Choose the letter corresponding to the correct structure from the drop-down list provided.)
Correct Structure:
Assign signal number 4 (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 4 corresponds to hydrogen(s):
Transcribed Image Text:Choose from the constitutional isomers below to assign a structure to this spectrum. b a f CH3 CH2CH3 CH3 CH3CH2CHCHCH3 b| d OH f CH3CH2CHCH2OH b c d e CH3CH2CH2CHCH2OH а b c d e g a a A B C (Choose the letter corresponding to the correct structure from the drop-down list provided.) Correct Structure: Assign signal number 4 (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 4 corresponds to hydrogen(s):
The following is the predicted 'H-NMR spectrum for an unknown compound with molecular formula C6 H140. This compound is a liquid at room
temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas.
3H
Hint: this signal is a
pair of overlapping
2H multiplets
1
3H
4
2H
1H
5
1H
3
PPM
Choose from the constitutional isomers below to assign a structure to this spectrum.
e
b
a
f
CH3
CH2CH3
CH3
CH3CH2CHCHCH3 CH,CH,CHCH,OH CH;CH2CH2CHCH2OH
a bld
OH f
CH3CH2CHCH2OH CH3CH2CH2ČHCH2OH
a b c
a b c de
de g
A
B
Transcribed Image Text:The following is the predicted 'H-NMR spectrum for an unknown compound with molecular formula C6 H140. This compound is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. 3H Hint: this signal is a pair of overlapping 2H multiplets 1 3H 4 2H 1H 5 1H 3 PPM Choose from the constitutional isomers below to assign a structure to this spectrum. e b a f CH3 CH2CH3 CH3 CH3CH2CHCHCH3 CH,CH,CHCH,OH CH;CH2CH2CHCH2OH a bld OH f CH3CH2CHCH2OH CH3CH2CH2ČHCH2OH a b c a b c de de g A B
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