Homework Help is Here – Start Your Trial Now!
Science
Chemistry
Step 1: Brief Description The given compound is 4-aminobenzoic acid. The IR and NMR spectrum of this compound also given. Determine the spectrum. Step 2: Determination of IR data The peaks are identified as following: Two bands at 3300 & 3230 cm. This is due to asymmetrical and symmetrical N-H stretching of NH₂ group. A broad stretching between $200-2500 cm** - This broad stretching is due to O-H in carboxylic acid group. Band at 1680-1700 cm¹. C=O Stretching 1600 cm C-C-C (aromatic carbon) Step 3: Determination of PMR spectrum Splitting patterns: It should be noted that spin-spin splitting is observed only between nonequivalent neighboring protons. Equivalent protons do spin-spin couple with one another but splitting is not observed. Chemical shift: A highly shielded proton has a low chemical shift and a highly deshielded proton has a high value of chemical shift. The given peaks are of following: Proton Level Chemical shift (ppm) Relative integration Multiplicity ABC -11.9 7.8 8.3 broad singlet (N-H D -5.9 2H proton) 2H %%%% 1H broad singlet (OH proton) 2H doublet doublet C. The amine group is considered to be electron donating toward the ring by resonance, thus it will place a partial negative charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. H H d. The carboxylic acid is considered to be electron withdrawing by resonance, thus it will place a partial positive charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. e. Based on the resonance structures, which of the aromatic protons is more shielded and which is less shielded? Which of these protons will appear at the larger chemical shift and which will appear at the lower chemical shift? Decide which of the protons should be labelled as HB and Hc. Explain briefly.

Step 1: Brief Description The given compound is 4-aminobenzoic acid. The IR and NMR spectrum of this compound also given. Determine the spectrum. Step 2: Determination of IR data The peaks are identified as following: Two bands at 3300 & 3230 cm. This is due to asymmetrical and symmetrical N-H stretching of NH₂ group. A broad stretching between $200-2500 cm** - This broad stretching is due to O-H in carboxylic acid group. Band at 1680-1700 cm¹. C=O Stretching 1600 cm C-C-C (aromatic carbon) Step 3: Determination of PMR spectrum Splitting patterns: It should be noted that spin-spin splitting is observed only between nonequivalent neighboring protons. Equivalent protons do spin-spin couple with one another but splitting is not observed. Chemical shift: A highly shielded proton has a low chemical shift and a highly deshielded proton has a high value of chemical shift. The given peaks are of following: Proton Level Chemical shift (ppm) Relative integration Multiplicity ABC -11.9 7.8 8.3 broad singlet (N-H D -5.9 2H proton) 2H %%%% 1H broad singlet (OH proton) 2H doublet doublet C. The amine group is considered to be electron donating toward the ring by resonance, thus it will place a partial negative charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. H H d. The carboxylic acid is considered to be electron withdrawing by resonance, thus it will place a partial positive charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. e. Based on the resonance structures, which of the aromatic protons is more shielded and which is less shielded? Which of these protons will appear at the larger chemical shift and which will appear at the lower chemical shift? Decide which of the protons should be labelled as HB and Hc. Explain briefly.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
See similar textbooks
icon
Related questions
Question
Step 1: Brief Description The given compound is 4-aminobenzoic acid. The IR and NMR spectrum of this compound also given. Determine the spectrum. Step 2: Determination of IR data The peaks are identified as following: Two bands at 3300 & 3230 cm. This is due to asymmetrical and symmetrical N-H stretching of NH₂ group. A broad stretching between $200-2500 cm** - This broad stretching is due to O-H in carboxylic acid group. Band at 1680-1700 cm¹. C=O Stretching 1600 cm C-C-C (aromatic carbon) Step 3: Determination of PMR spectrum Splitting patterns: It should be noted that spin-spin splitting is observed only between nonequivalent neighboring protons. Equivalent protons do spin-spin couple with one another but splitting is not observed. Chemical shift: A highly shielded proton has a low chemical shift and a highly deshielded proton has a high value of chemical shift. The given peaks are of following: Proton Level Chemical shift (ppm) Relative integration Multiplicity ABC -11.9 7.8 8.3 broad singlet (N-H D -5.9 2H proton) 2H %%%% 1H broad singlet (OH proton) 2H doublet doublet
Transcribed Image Text:Step 1: Brief Description The given compound is 4-aminobenzoic acid. The IR and NMR spectrum of this compound also given. Determine the spectrum. Step 2: Determination of IR data The peaks are identified as following: Two bands at 3300 & 3230 cm. This is due to asymmetrical and symmetrical N-H stretching of NH₂ group. A broad stretching between $200-2500 cm** - This broad stretching is due to O-H in carboxylic acid group. Band at 1680-1700 cm¹. C=O Stretching 1600 cm C-C-C (aromatic carbon) Step 3: Determination of PMR spectrum Splitting patterns: It should be noted that spin-spin splitting is observed only between nonequivalent neighboring protons. Equivalent protons do spin-spin couple with one another but splitting is not observed. Chemical shift: A highly shielded proton has a low chemical shift and a highly deshielded proton has a high value of chemical shift. The given peaks are of following: Proton Level Chemical shift (ppm) Relative integration Multiplicity ABC -11.9 7.8 8.3 broad singlet (N-H D -5.9 2H proton) 2H %%%% 1H broad singlet (OH proton) 2H doublet doublet
C. The amine group is considered to be electron donating toward the ring by resonance, thus it will place a partial negative charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. H H d. The carboxylic acid is considered to be electron withdrawing by resonance, thus it will place a partial positive charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. e. Based on the resonance structures, which of the aromatic protons is more shielded and which is less shielded? Which of these protons will appear at the larger chemical shift and which will appear at the lower chemical shift? Decide which of the protons should be labelled as HB and Hc. Explain briefly.
Transcribed Image Text:C. The amine group is considered to be electron donating toward the ring by resonance, thus it will place a partial negative charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. H H d. The carboxylic acid is considered to be electron withdrawing by resonance, thus it will place a partial positive charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. e. Based on the resonance structures, which of the aromatic protons is more shielded and which is less shielded? Which of these protons will appear at the larger chemical shift and which will appear at the lower chemical shift? Decide which of the protons should be labelled as HB and Hc. Explain briefly.
AI-Generated Solution
AI-generated content may present inaccurate or offensive content that does not represent bartleby’s views.
steps

Unlock instant AI solutions

Tap the button
to generate a solution

SEE SOLUTION
Similar questions
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY
SEE MORE TEXTBOOKS