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

IR Spect:Drawing Spectra

Organic Chemistry

15. Analytical Techniques:IR, NMR, Mass Spect

IR Spect:Drawing Spectra

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1:52 minutes

Problem 52

Textbook Question

Hoping to make the following diene, a chemist treated the diol shown with acid. Based on the IR spectrum, was the reaction successful? If not, what compound was made instead?
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Verified step by step guidance

Identify the starting material: The problem mentions a diol, which is a compound containing two hydroxyl (OH) groups. Determine the structure of the diol based on the context provided in Chapter 13.

Understand the reaction conditions: The diol is treated with acid. This typically suggests a dehydration reaction, where water is removed to form a double bond, potentially leading to the formation of a diene.

Analyze the IR spectrum: Look for key absorptions. A successful conversion to a diene would show a decrease or absence of O-H stretching vibrations (around 3200-3600 cm^-1) and the presence of C=C stretching vibrations (around 1600-1680 cm^-1).

Determine the success of the reaction: If the IR spectrum shows the expected changes, the reaction likely produced the desired diene. If not, consider what other functional groups might be present, indicating a different product.

Consider alternative products: If the reaction was not successful, the presence of other peaks in the IR spectrum, such as C=O stretching (around 1700 cm^-1), might suggest the formation of a different compound, such as a ketone or aldehyde, due to rearrangement or incomplete dehydration.

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Key Concepts

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

Infrared (IR) Spectroscopy

IR spectroscopy is a technique used to identify functional groups in a molecule by measuring the absorption of infrared light, which causes molecular vibrations. Each type of bond and functional group absorbs at characteristic frequencies, allowing chemists to deduce structural information about the compound. In this context, analyzing the IR spectrum can help determine if the desired diene was formed by checking for the presence or absence of specific absorption bands.

Dehydration Reaction

A dehydration reaction involves the removal of water (H2O) from a molecule, often facilitated by an acid catalyst. In organic chemistry, this reaction is commonly used to convert alcohols into alkenes, such as dienes, by eliminating water. Understanding this mechanism is crucial for predicting the outcome of treating a diol with acid, as it helps determine whether the desired diene or another product was formed.

Diene Formation

Dienes are hydrocarbons with two double bonds, and their formation often involves the elimination of water from diols. The success of this transformation depends on the reaction conditions and the stability of the resulting diene. Recognizing the structural features and stability factors that favor diene formation is essential for evaluating whether the reaction proceeded as intended or if an alternative product was generated.

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Textbook Question

Match each of the four IR spectra to one of the given compounds. [One of the compounds does not match a spectrum.]

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Textbook Question

Match each of the four IR spectra to one of the given compounds. [One of the compounds does not match a spectrum.]

Textbook Question

What functional groups might be present in the IR spectra for the molecules with the given molecular formulas. [Be sure to use the molecular formula in your analysis.]

(b) C₃H₄O₄

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Textbook Question

Given the IR spectrum, suggest what functional groups might correspond to the given molecular formula.

(d) C₇H₅O

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Textbook Question

What functional groups are present in a molecule with a molecular formula of C₄H₁₀O and the following IR spectrum? [Use Table 14.2 for this.]

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Textbook Question

On a day in which the laboratory air conditioning stopped working, a chemist hypothesized that the atmosphere would provide enough ambient heat to drive the nitrile hydrolysis reaction to the carboxylic acid. Based on the IR of the resulting product, was this hypothesis correct?

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Textbook Question

Given the IR spectrum, suggest what functional groups might correspond to the given molecular formula.

(b) C₃H₇NO

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Textbook Question

Which one of the following five compounds produced the IR spectrum shown below?

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