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 33c

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)

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Identify the structure of the isopropyl group, which is (CH₃)₂CH−. It consists of two methyl groups (CH₃) and one methine group (CH).

Consider the NMR chemical environment: The two methyl groups are equivalent and will produce a single signal. The methine group is in a different environment and will produce another signal.

Determine the integration pattern: The integration ratio reflects the number of protons. The two methyl groups contribute 6 protons, and the methine group contributes 1 proton. Thus, the integration ratio is 6:1.

Analyze the multiplicity: The methine proton is adjacent to 6 equivalent protons (from the two methyl groups), so it will appear as a septet due to the n+1 rule (where n is the number of neighboring protons).

The methyl protons are adjacent to 1 methine proton, so they will appear as a doublet. Therefore, the expected NMR pattern for an isopropyl group is a doublet for the methyl protons and a septet for the methine proton.

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Key Concepts

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

NMR Spectroscopy

Nuclear Magnetic Resonance (NMR) spectroscopy is a technique used to determine the structure of organic compounds by analyzing the magnetic properties of atomic nuclei. It provides information about the number of hydrogen atoms (integration) and their environment (multiplicity), which helps in identifying functional groups and structural features.

Integration in NMR

Integration in NMR refers to the area under the peaks in the spectrum, which is proportional to the number of hydrogen atoms contributing to that signal. For isopropyl groups, integration helps determine the relative number of hydrogens in different environments, typically showing a ratio that reflects the CH and CH3 groups present.

Multiplicity in NMR

Multiplicity in NMR describes the splitting pattern of peaks, which occurs due to spin-spin coupling between neighboring hydrogen atoms. In isopropyl groups, the CH hydrogen is typically split into a doublet by the adjacent CH3 groups, while the CH3 hydrogens appear as a septet due to coupling with the CH hydrogen, indicating the connectivity and environment of these atoms.

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Related Practice

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.]

(f)

Textbook Question

How would integration distinguish the ¹H NMR spectra of the following compounds?

Textbook Question

(c)

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.

(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.

(c)

Textbook Question

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

(d)

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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)

Key Concepts

NMR Spectroscopy

Integration in NMR

Multiplicity in NMR

Watch next

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)