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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3:59 minutes

Problem 69

Textbook Question

Assign the peaks in the ¹H NMR spectrum for the molecule shown.
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Verified step by step guidance

Identify the different types of hydrogen environments in the molecule. Look for unique hydrogen atoms that are in different chemical environments due to their bonding and the presence of nearby electronegative atoms or π systems.

Determine the chemical shift range for each type of hydrogen. Use known chemical shift ranges for different types of hydrogens, such as alkyl, alkenyl, aromatic, or those near electronegative atoms.

Consider the splitting pattern for each peak. The splitting pattern is determined by the number of neighboring hydrogens (n+1 rule), where n is the number of adjacent hydrogens.

Estimate the integration of each peak. The integration corresponds to the relative number of hydrogens contributing to each signal, which helps in assigning the peaks to specific hydrogen environments.

Match each peak in the ¹H NMR spectrum with the identified hydrogen environments based on chemical shift, splitting pattern, and integration. Assign the peaks accordingly to complete the analysis.

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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 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 the spectrum correspond to different hydrogen environments, helping to deduce molecular structure.

Chemical Shift

Chemical shift in ¹H NMR refers to the position of the NMR signal relative to a standard reference, typically tetramethylsilane (TMS). It indicates the electronic environment surrounding a hydrogen atom, influenced by nearby electronegative atoms or functional groups. Chemical shifts help identify the type of hydrogen present, such as aromatic, aliphatic, or hydroxyl hydrogens.

Spin-Spin Coupling

Spin-spin coupling, or J-coupling, occurs when hydrogen atoms influence each other's magnetic fields, 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. Understanding coupling helps in determining the connectivity and arrangement of atoms within a molecule.

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Sonogashira Coupling Reaction

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Related Practice

Textbook Question

Draw the ¹H NMR spectrum you would expect to see for each of the molecules in Assessment 15.63.

(c)

Textbook Question

Draw the ¹H NMR spectrum you would expect to see for each of the molecules in Assessment 15.63.

(d)

Textbook Question

Draw a spectrum for each of the following molecules, being sure to indicate the multiplicity, integration, and chemical shift of each peak. Label each signal based on the set of equivalent hydrogens to which it corresponds.

(b)

Textbook Question

(c)

Textbook Question

The spectrum shown here is for a molecule with a molecular formula of C₄H₉Cl. Suggest a structure for this molecule.

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Textbook Question

When a compound with molecular formula C₁₁H₁₄O₂ undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following ¹H NMR spectrum. Identify the compound.

Textbook Question

How many signals would the product of the following reaction show in

a. its ¹H NMR spectrum?

b. its ¹³C NMR spectrum?

Textbook Question

The following NMR spectra correspond to compound of formula (C) C₆H₁₀O₂. Propose structure, and show how it is consistent with the observed absorptions.

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Assign the peaks in the ¹H NMR spectrum for the molecule shown.<IMAGE>

Key Concepts

¹H NMR Spectroscopy

Chemical Shift

Spin-Spin Coupling

Assign the peaks in the ¹H NMR spectrum for the molecule shown.
<IMAGE>