Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

15. Analytical Techniques:IR, NMR, Mass Spect

NMR Integration

Organic Chemistry

15. Analytical Techniques:IR, NMR, Mass Spect

NMR Integration

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Problem 76

Textbook Question

For the compound shown, produce a table of the shift, integration, and multiplicity of each peak you would expect to see in a ¹H NMR spectrum.

Verified step by step guidance

Identify the different types of hydrogen environments in the compound. Look for unique groups or atoms that might affect the chemical shift, such as electronegative atoms or pi bonds.

Estimate the chemical shift for each type of hydrogen. Use typical chemical shift ranges for common functional groups and environments. For example, alkane hydrogens typically appear between 0-2 ppm, while hydrogens on a carbon adjacent to an electronegative atom might appear between 3-4 ppm.

Determine the integration for each peak. This corresponds to the number of hydrogens in each environment. Count the hydrogens in each distinct environment to determine the relative area under each peak.

Analyze the multiplicity of each peak. Consider the number of neighboring hydrogens (n) and apply the n+1 rule to determine the splitting pattern. For example, a hydrogen with two neighboring hydrogens will appear as a triplet.

Create a table summarizing the chemical shift, integration, and multiplicity for each type of hydrogen in the compound. Ensure that each entry in the table corresponds to a distinct hydrogen environment identified in the first step.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Chemical Shift in ¹H NMR

Chemical shift refers to the position of an NMR signal relative to a standard reference, typically tetramethylsilane (TMS). It indicates the electronic environment of hydrogen atoms in a molecule, affected by nearby electronegative atoms or functional groups. Understanding chemical shifts helps predict where peaks will appear in the spectrum.

Integration in ¹H NMR

Integration in ¹H NMR quantifies the area under each peak, corresponding to the number of hydrogen atoms contributing to that signal. It provides insight into the relative number of protons in different environments within the molecule, aiding in determining the molecular structure.

Multiplicity in ¹H NMR

Multiplicity describes the splitting pattern of NMR signals, resulting from spin-spin coupling between neighboring hydrogen atoms. The number of peaks in a multiplet follows the n+1 rule, where n is the number of adjacent protons. Multiplicity reveals information about the connectivity and proximity of hydrogen atoms in the molecule.

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Related Practice

Textbook Question

Complete the table of ¹H NMR data you'd generate for each of the following molecules.

(b)

Textbook Question

Complete the table of ¹H NMR data you'd generate for each of the following molecules.

(c)

Textbook Question

Complete the table of ¹H NMR data you'd generate for each of the following molecules.

(d)

Textbook Question

Draw the peak that would correspond to the hydrogens at C₃ in the molecule shown. Be sure to indicate the integration and place it at an appropriate chemical shift.

Textbook Question

Determine the ratios of the chemically nonequivalent protons in a compound if the steps of the integration curves measure 40.5, 27, 13, and 118 mm, from left to right across the spectrum. Draw the structure of a compound whose ¹H NMR spectrum would show these integrals in the observed order.

Multiple Choice

PRACTICE: Which of the following molecules gives a 1H NMR spectrum consisting of three peaks with integral ratio of 3:1:6 (when signals are counted from left to right)?

Multiple Choice

Which property of a signal contains the number of hydrogen atoms in the set of equivalent hydrogen atoms that caused the signal in a ¹H NMR spectrum?

Textbook Question

For the following molecules, give the integration you would expect for the signal associated with the hydrogens at the labeled carbons. [Pay attention to the symmetry, or lack of symmetry, in the molecules.]

(e)

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