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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6:04 minutes

Problem 81b

Textbook Question

(b) Provide an arrow-pushing mechanism for the reaction.
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Verified step by step guidance

Step 1: Analyze the ¹H NMR spectrum to identify the number of unique hydrogen environments. Count the number of distinct signals, which corresponds to the number of different types of hydrogen atoms in the molecule.

Step 2: Examine the chemical shift of each signal in the ¹H NMR spectrum. Use the chemical shift values to infer the electronic environment of the hydrogens, which can help identify functional groups or structural features.

Step 3: Look at the splitting patterns of each signal in the ¹H NMR spectrum. The splitting pattern (singlet, doublet, triplet, etc.) provides information about the number of neighboring hydrogens, which can help deduce the connectivity of the molecule.

Step 4: For the arrow-pushing mechanism, identify the starting materials and the product of the reaction. Determine the functional groups involved and the type of reaction (e.g., substitution, elimination, addition).

Step 5: Draw the mechanism by showing the movement of electrons with arrows. Start with the nucleophile and electrophile interaction, and illustrate each step of the reaction, ensuring to show the formation and breaking of bonds, and the intermediates formed during the process.

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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 properties of hydrogen nuclei. It provides information about the number of hydrogen atoms, their environment, and how they are connected within a molecule. Key features include chemical shifts, multiplicity, and integration, which help identify functional groups and molecular structure.

Arrow-Pushing Mechanism

Arrow-pushing is a method used in organic chemistry to illustrate the movement of electrons during chemical reactions. It involves drawing arrows to show how electron pairs move from one atom or bond to another, helping to visualize the step-by-step transformation of reactants into products. Understanding this concept is crucial for predicting reaction outcomes and mechanisms.

Reaction Mechanism

A reaction mechanism is a detailed description of the step-by-step process by which reactants are converted into products in a chemical reaction. It includes the sequence of elementary steps, intermediates, and transition states, providing insight into the kinetics and thermodynamics of the reaction. Understanding mechanisms is essential for designing and optimizing chemical processes.

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Related Practice

Textbook Question

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

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Textbook Question

When compound A (C₅H₁₂O) is treated with HBr, it forms compound B (C₅H₁₁Br). The ¹H NMR spectrum of compound A has a 1H singlet, a 3H doublet, a 6H doublet, and two 1H multiplets. The ¹H NMR spectrum of compound B has a 6H singlet, a 3H triplet, and a 2H quartet. Identify compounds A and B.

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Textbook Question

In the lab, ¹H NMR is often used to verify that a reaction has worked as expected by comparing the product spectrum with what is expected. Given the ¹H NMR of the reactant shown, draw the spectrum you'd expect to see of the product that results.

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Textbook Question

(a) Using the ¹H NMR spectra, identify the reactants and product for this reaction.

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Textbook Question

Without worrying about the relative location of the signals (i.e., the chemical shift) or the splitting patterns, draw a spectrum of the following molecule, being sure to indicate the integration of each peak. Label each signal based on the set of equivalent hydrogens to which it corresponds. [We expand on this question in future assessments.]

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Textbook Question

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

(b)

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Textbook Question

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

(c)

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