The given compound is ethyl-4-amino-benzoate or benzocaine. The peaks are identified as following: Frequency 3300 and 3230 cm" 3100 cm 2880 cm 1750cm 1610 cm $250 cm Step 2: Determining 1H NMR data: The given peaks are of following: Proton label Bond Type -NH, Stretch (medium and weak) C-H Stretch (sp₂) (medium and sharp) C-H Stretch (sp3) (weak) C=O Stretch (strong and sharp) C=C Stretch (strong and sharp) C-O Stretch (strong and sharp) Relative integration expected Chemical shift (ppm) Multicipity (or observed) 2H (Two peaks in aromatic doublet A 7.8 ppm region) 2H (Two peaks in aromatic 6.7 ppm doublet region) C 4.3 ppm 2H (for CH₂) quartet broad peak for amino group (NH) which is merged with broad peak with D 4.1 ppm quartet signal of CH₂ E 1.3 ppm SH (for CH₂) merged quartet triplet Step 3: Determination of structure: The structure is: NH₂ CH₂ C. The NMR spectrum shown below represents the product (ethyl 4-aminobenzoate) after it has been shaken with deuterium oxide (D₂O). Write the equation for the reaction which occurs when D₂O reacts with ethyl 4-aminobenzoate. Draw the structure of the compound next to the spectrum and label the protons so that they match the letter labels shown on the NMR spectrum. Fill in the Chemical shift, integration and multiplicity in the table. D. on the results of the "D20 shake". What happened to the signal which had been caused by HD? Explain briefly. B' A 10 ppm EQUATION: 5 ppm E υ C' STRUCTURE: Proton label Chemical shift | Relative integration Multiplicity (ppm) A' B' C' 0 ppm E' Comment on the results of the "D20 shake". What happened to the signal which had been caused by HD? Explain briefly.
The given compound is ethyl-4-amino-benzoate or benzocaine. The peaks are identified as following: Frequency 3300 and 3230 cm" 3100 cm 2880 cm 1750cm 1610 cm $250 cm Step 2: Determining 1H NMR data: The given peaks are of following: Proton label Bond Type -NH, Stretch (medium and weak) C-H Stretch (sp₂) (medium and sharp) C-H Stretch (sp3) (weak) C=O Stretch (strong and sharp) C=C Stretch (strong and sharp) C-O Stretch (strong and sharp) Relative integration expected Chemical shift (ppm) Multicipity (or observed) 2H (Two peaks in aromatic doublet A 7.8 ppm region) 2H (Two peaks in aromatic 6.7 ppm doublet region) C 4.3 ppm 2H (for CH₂) quartet broad peak for amino group (NH) which is merged with broad peak with D 4.1 ppm quartet signal of CH₂ E 1.3 ppm SH (for CH₂) merged quartet triplet Step 3: Determination of structure: The structure is: NH₂ CH₂ C. The NMR spectrum shown below represents the product (ethyl 4-aminobenzoate) after it has been shaken with deuterium oxide (D₂O). Write the equation for the reaction which occurs when D₂O reacts with ethyl 4-aminobenzoate. Draw the structure of the compound next to the spectrum and label the protons so that they match the letter labels shown on the NMR spectrum. Fill in the Chemical shift, integration and multiplicity in the table. D. on the results of the "D20 shake". What happened to the signal which had been caused by HD? Explain briefly. B' A 10 ppm EQUATION: 5 ppm E υ C' STRUCTURE: Proton label Chemical shift | Relative integration Multiplicity (ppm) A' B' C' 0 ppm E' Comment on the results of the "D20 shake". What happened to the signal which had been caused by HD? Explain briefly.
Chapter20: Carboxylic Acids And Nitriles
Section20.SE: Something Extra
Problem 67AP
Related questions
Question
Transcribed Image Text:The given compound is ethyl-4-amino-benzoate or benzocaine.
The peaks are identified as following:
Frequency
3300 and 3230 cm"
3100 cm
2880 cm
1750cm
1610 cm
$250 cm
Step 2: Determining 1H NMR data:
The given peaks are of following:
Proton label
Bond Type
-NH, Stretch (medium and weak)
C-H Stretch (sp₂) (medium and sharp)
C-H Stretch (sp3) (weak)
C=O Stretch (strong and sharp)
C=C Stretch (strong and sharp)
C-O Stretch (strong and sharp)
Relative integration expected
Chemical shift (ppm)
Multicipity
(or observed)
2H (Two peaks in aromatic
doublet
A
7.8 ppm
region)
2H (Two peaks in aromatic
6.7 ppm
doublet
region)
C
4.3 ppm
2H (for CH₂)
quartet
broad peak for amino group
(NH) which is merged with
broad peak with
D
4.1 ppm
quartet signal of CH₂
E
1.3 ppm
SH (for CH₂)
merged quartet
triplet
Step 3: Determination of structure:
The structure is:
NH₂
CH₂
Transcribed Image Text:C.
The NMR spectrum shown below represents the product (ethyl 4-aminobenzoate) after it has been shaken with
deuterium oxide (D₂O). Write the equation for the reaction which occurs when D₂O reacts with ethyl 4-aminobenzoate.
Draw the structure of the compound next to the spectrum and label the protons so that they match the letter labels
shown on the NMR spectrum. Fill in the Chemical shift, integration and multiplicity in the table.
D. on the results of the "D20 shake". What happened to the signal which had been caused by HD? Explain briefly.
B'
A
10 ppm
EQUATION:
5 ppm
E
υ
C'
STRUCTURE:
Proton
label
Chemical shift | Relative integration
Multiplicity
(ppm)
A'
B'
C'
0 ppm
E'
Comment on the results of the "D20 shake". What happened to the signal which had been caused
by HD? Explain briefly.
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