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 63c

Textbook Question

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

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Identify the structure of the molecule in question. Determine the number of hydrogen atoms and their environment within the molecule. This will help in predicting the number of signals in the ¹H NMR spectrum.

Determine the chemical shift for each type of hydrogen. Chemical shifts are influenced by the electronic environment surrounding the hydrogen atoms. Consider factors such as electronegativity of nearby atoms, hybridization, and aromaticity.

Assess the splitting pattern for each signal. The splitting pattern is determined by the number of neighboring hydrogen atoms (n+1 rule), where n is the number of adjacent hydrogens.

Calculate the integration of each signal. Integration corresponds to the number of hydrogen atoms contributing to each signal, providing information about the relative number of hydrogens in each environment.

Compile the data into a table format, listing the chemical shift, splitting pattern, and integration for each type of hydrogen in the molecule. This will provide a comprehensive overview of the ¹H NMR data for the molecule.

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Key Concepts

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

¹H NMR Spectroscopy

¹H NMR (Proton Nuclear Magnetic Resonance) spectroscopy is a technique used to determine the structure of organic compounds by analyzing the magnetic environment of hydrogen atoms. It provides information about the number of hydrogen atoms, their chemical environment, and how they are connected within a molecule. Peaks in an NMR spectrum correspond to different hydrogen environments, and their chemical shifts, multiplicity, and integration help deduce structural details.

Chemical Shift

Chemical shift in ¹H NMR refers to the position of an NMR signal relative to a standard reference compound, usually tetramethylsilane (TMS). It is measured in parts per million (ppm) and indicates the electronic environment of hydrogen atoms. Factors such as electronegativity of nearby atoms, hybridization, and hydrogen bonding can influence chemical shifts, helping to identify functional groups and structural features in a molecule.

Spin-Spin Coupling

Spin-spin coupling, also known as J-coupling, occurs when non-equivalent hydrogen atoms influence each other's magnetic environment, causing splitting of NMR signals into multiplets. The pattern and number of peaks in a multiplet provide information about the number of neighboring hydrogen atoms (n+1 rule) and their spatial relationship. This coupling helps elucidate the connectivity and relative positions of atoms within a molecule.

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Related Practice

Textbook Question

For the molecules shown, give the number of signals expected and the relative ratio of the signal integrations.

(b)

Textbook Question

Being able to recognize patterns of integration and multiplicity for common functional groups makes structure identification more efficient. Draw the pattern of integration and multiplicity you'd expect to see for each common alkyl group.

(c)

Textbook Question

(d)

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.

(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

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.

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.

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

Key Concepts

¹H NMR Spectroscopy

Chemical Shift

Spin-Spin Coupling

Watch next

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