d. For the spectrum for product, identify which functional groups are suggested by the signals indicated by each of the include whether the signal is d to a stretching vibration or a bending vibration for the question) For the NMR spect for product 8, draw the structure of the product next to the spectrum and label the prote they match the labels shown on the NMR spectrum Fil in the Chemical shi, donand mulipácity in the table STRUCTURE Doublet Prote a H (ppm) L Explain the multiplicity and relative integration for the peak labda Explain the multiplicity and relativa integration for the peak abeed Hr.

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
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.42P
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d. For the IR spectrum for product B, identify which functional groups are suggested by the signals indicated by each of the
arrows. (Be sure to include whether the signal is due to a stretching vibration or a banding vibration for this question.)
mmm
t.
For the NMR spectrum for product B, draw the structure of the product next to the spectrum and label the proton so that
they match the letter labels shown on the NMR spectrum. Fill in the Chemical shift, inkgosion, and multiplicity in the table.
9
Septe
STRUCTURE:
Integration-1
Doublet
Integration - 6
Proton
label
F
H
Chemical R
(ppm)
Explain the multiplicity and relative integration for the peak labelled Ha.
Explain the multiplicity and relative integration for the peak labelled Hr.
Rev
integration
Multiply
Transcribed Image Text:d. For the IR spectrum for product B, identify which functional groups are suggested by the signals indicated by each of the arrows. (Be sure to include whether the signal is due to a stretching vibration or a banding vibration for this question.) mmm t. For the NMR spectrum for product B, draw the structure of the product next to the spectrum and label the proton so that they match the letter labels shown on the NMR spectrum. Fill in the Chemical shift, inkgosion, and multiplicity in the table. 9 Septe STRUCTURE: Integration-1 Doublet Integration - 6 Proton label F H Chemical R (ppm) Explain the multiplicity and relative integration for the peak labelled Ha. Explain the multiplicity and relative integration for the peak labelled Hr. Rev integration Multiply
a)
M₂C.
Step 4: c) 1H-NMR analysis of product A
C
D
The hydrolysis of an emide involves the cleavage of the amide bond, which is a carbonyl group (C=0)
bonded to a nitrogen atom. This reaction is typically catalyzed by an acid or a base.
E
Step 3: b)IR analysis of product A:
The broad peaks in the range of 3500 cm³ to 2500cm* indicate O-H stretching frequency of COOH
functional group...
The strong, narrow peak around 1720 cm* indicates C=0 stretching frequency of COOH.
The medium, sharp peak around 1600cm* indicates C-C stretching frequency of benzene ring
Proton A: The small, broad peak around 12 ppm indicates O-H of COOH.
Proton B and proton C: The doublets at 8.1ppm, 7.1ppm indicate di-substituted benzene.
Proton D: The quartet at 2.4 ppm indicate CH₂ unit with adjacent CH₂ unit.
Proton E: Triplet et 1.1 ppm indicate CH₂ unit with adjacent CH₂ unit.
Proton label
relative integration
A
1
B
1
1
2
3
Solution
HH₂O
Heat H₂G.
1600 cm
Product A
chemical shift
12ppm
8.1ppm
7.1ppm
24ppm
1.1ppm
H₂C.
H
OH
a) Hydrolysis of amide yields an acid and amine.
b) and c) The IR peak showing functional group and chemical shift values of proton for the given amide is
shown below
1720 cm1
8.1ppm, doublet. H
NH₂
Product B
12ppm broad singlet, IH
3500-2550 cm
7.1ppm, doublet, IH
multiplicity
broad singlet
doublet
doublet
quartet
triplet
Transcribed Image Text:a) M₂C. Step 4: c) 1H-NMR analysis of product A C D The hydrolysis of an emide involves the cleavage of the amide bond, which is a carbonyl group (C=0) bonded to a nitrogen atom. This reaction is typically catalyzed by an acid or a base. E Step 3: b)IR analysis of product A: The broad peaks in the range of 3500 cm³ to 2500cm* indicate O-H stretching frequency of COOH functional group... The strong, narrow peak around 1720 cm* indicates C=0 stretching frequency of COOH. The medium, sharp peak around 1600cm* indicates C-C stretching frequency of benzene ring Proton A: The small, broad peak around 12 ppm indicates O-H of COOH. Proton B and proton C: The doublets at 8.1ppm, 7.1ppm indicate di-substituted benzene. Proton D: The quartet at 2.4 ppm indicate CH₂ unit with adjacent CH₂ unit. Proton E: Triplet et 1.1 ppm indicate CH₂ unit with adjacent CH₂ unit. Proton label relative integration A 1 B 1 1 2 3 Solution HH₂O Heat H₂G. 1600 cm Product A chemical shift 12ppm 8.1ppm 7.1ppm 24ppm 1.1ppm H₂C. H OH a) Hydrolysis of amide yields an acid and amine. b) and c) The IR peak showing functional group and chemical shift values of proton for the given amide is shown below 1720 cm1 8.1ppm, doublet. H NH₂ Product B 12ppm broad singlet, IH 3500-2550 cm 7.1ppm, doublet, IH multiplicity broad singlet doublet doublet quartet triplet
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