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 Practice

Organic Chemistry

15. Analytical Techniques:IR, NMR, Mass Spect

NMR Practice

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5:40 minutes

Problem 28g

Textbook Question

Describe the ¹H NMR spectrum you would expect for each of the following compounds, indicating the relative positions of the signals:
g. CH₃CH₂OCH₂CH₃

Verified step by step guidance

Step 1: Begin by identifying the structure of the compound. Determine the number of unique hydrogen environments in the molecule. Each unique environment corresponds to a distinct signal in the 1H NMR spectrum.

Step 2: Analyze the chemical shift for each hydrogen environment. Chemical shifts are influenced by factors such as electronegativity of nearby atoms, hybridization of the carbon atom to which the hydrogen is attached, and proximity to functional groups. Use typical chemical shift ranges to predict the approximate position of each signal.

Step 3: Determine the splitting pattern (multiplicity) for each signal. The splitting is caused by spin-spin coupling with neighboring hydrogens. Use the n+1 rule, where n is the number of equivalent neighboring hydrogens, to predict the multiplicity (e.g., singlet, doublet, triplet, etc.).

Step 4: Evaluate the relative integration of each signal. The integration corresponds to the number of hydrogens in each environment. For example, a signal representing three hydrogens (e.g., a methyl group) will have three times the integration of a signal representing one hydrogen.

Step 5: Summarize the expected 1H NMR spectrum by listing the number of signals, their approximate chemical shifts, splitting patterns, and relative integrations. This provides a complete description of the spectrum for the given compound.

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Key Concepts

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

1H NMR Spectroscopy

Proton Nuclear Magnetic Resonance (1H NMR) spectroscopy is a powerful analytical technique used to determine the structure of organic compounds. It works by measuring the magnetic environment of hydrogen atoms in a molecule, providing information about the number of hydrogen atoms, their chemical environment, and the connectivity of the molecule. The resulting spectrum displays peaks that correspond to different hydrogen environments, allowing chemists to infer structural details.

Chemical Shift

Chemical shift refers to the position of a signal in an NMR spectrum, measured in parts per million (ppm). It indicates the electronic environment surrounding a hydrogen atom, influenced by factors such as electronegativity and hybridization. Different functional groups and molecular structures lead to distinct chemical shifts, which help in identifying the types of hydrogen present in a compound and their relative positions in the molecule.

Integration and Multiplicity

Integration in 1H NMR refers to the area under each peak, which correlates to the number of hydrogen atoms contributing to that signal. Multiplicity describes the splitting pattern of the peaks, which arises from the interaction of neighboring hydrogen atoms (n+1 rule). Understanding integration and multiplicity is crucial for determining the number of hydrogen atoms in different environments and the connectivity of the molecule, aiding in the elucidation of its structure.

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06:46

1H NMR Integration

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Related Practice

Textbook Question

Identify each of the following compounds from the ¹H NMR data and molecular formula:

c. C₅H₁₀O₂: a 3H triplet at 1.15 ppm

a 3H triplet at 1.25 ppm

a 2H quartet at 2.33 ppm

a 2H quartet at 4.13 ppm

Textbook Question

Describe the ¹H NMR spectrum you would expect for each of the following compounds, indicating the relative positions of the signals:

Textbook Question

Explain how the following compounds, each with the same molecular formula, could be distinguished by their ¹H NMR spectra.

Textbook Question

Describe the ¹H NMR spectrum you would expect for each of the following compounds, indicating the relative positions of the signals:

Textbook Question

The following ¹H NMR spectra are for four compounds, each with molecular formula of C₆H₁₂O₂. Identify the compounds.

c. <IMAGE>

Textbook Question

Sketch the following spectra that would be obtained for 2-chloroethanol:

b. The ¹H NMR spectrum for a sample of the alcohol that contains a trace amount of acid.

Textbook Question

Sketch the following spectra that would be obtained for 2-chloroethanol:

a. The ¹H NMR spectrum for an anhydrous sample of the alcohol.

Textbook Question

The ¹H NMR spectra of three isomers with molecular formula C₇H₁₄O are shown here. Which isomer produces which spectrum?

b. <IMAGE>

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Describe the 1H NMR spectrum you would expect for each of the following compounds, indicating the relative positions of the signals:g. CH3CH2OCH2CH3

Key Concepts

1H NMR Spectroscopy

Chemical Shift

Integration and Multiplicity

Describe the ¹H NMR spectrum you would expect for each of the following compounds, indicating the relative positions of the signals:
g. CH₃CH₂OCH₂CH₃