9. A student performs the following reaction in the laboratory, then takes a 'H NMR at the end of the reaction (shown below): 1. ONa ОН 2. H30* NMR: 3H 2H 2H 1H 12 10 8 4 6. PPM

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Chapter1: Chemical Foundations
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a) Based on the proton NMR shown, did the student obtain the desired product from their reaction? If not, what did they likely obtain instead? Assign all signals on the NMR to the structure you propose. 

b)Draw a mechanism for the reaction to obtain the structure you proposed in part a

Common 'H NMR Chemical Shifts
Chemical Shift Range
(рpm)
- 0.9-1.7
Functional Group Name
Еxample
Alkanes
H.
Allylic
- 2
Alkenes
Vinylic
~ 4.5-6.5
H.
Alkynes
Alkyl halides
2.5
-H-
~2-4
H.
а-Н's
~2-3
H.
Aldehyde
- 10
~
Carbonyls
TH.
- 12
Carboxylic
Acid
Carbons bound to Oxygen
~3-5
H.
H
RX
Alcohols
~2-5
-0-H
Amines
- 2-5
-N-H
Benzylic
- 2.5
H
Aromatic
Aryl
- 6.5-8
Degrees of Unsaturation formula:
2C + 2 + N — X — Н
DoU =
2
Transcribed Image Text:Common 'H NMR Chemical Shifts Chemical Shift Range (рpm) - 0.9-1.7 Functional Group Name Еxample Alkanes H. Allylic - 2 Alkenes Vinylic ~ 4.5-6.5 H. Alkynes Alkyl halides 2.5 -H- ~2-4 H. а-Н's ~2-3 H. Aldehyde - 10 ~ Carbonyls TH. - 12 Carboxylic Acid Carbons bound to Oxygen ~3-5 H. H RX Alcohols ~2-5 -0-H Amines - 2-5 -N-H Benzylic - 2.5 H Aromatic Aryl - 6.5-8 Degrees of Unsaturation formula: 2C + 2 + N — X — Н DoU = 2
9. A student performs the following reaction in the laboratory, then takes a 'H NMR at
the end of the reaction (shown below):
1.
ONa
ОН
2. H3O*
NMR:
3H
2H
2H
1H
12
10
2
6.
PPM
8.
4
Transcribed Image Text:9. A student performs the following reaction in the laboratory, then takes a 'H NMR at the end of the reaction (shown below): 1. ONa ОН 2. H3O* NMR: 3H 2H 2H 1H 12 10 2 6. PPM 8. 4
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