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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4:01 minutes

Problem 59

Textbook Question

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

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Verified step by step guidance

Analyze the IR spectrum provided and identify the key absorption peaks. Look for characteristic wavenumbers (in cm⁻¹) that correspond to specific functional groups. For example, a broad peak around 3200-3600 cm⁻¹ indicates an O-H stretch (alcohol or carboxylic acid), while a sharp peak near 1700 cm⁻¹ suggests a C=O stretch (carbonyl group).

Compare the identified functional groups from the IR spectrum with the functional groups present in each of the five compounds provided. Match the observed peaks to the possible functional groups in the compounds.

Pay attention to any unique or distinguishing peaks in the IR spectrum that can help differentiate between the compounds. For instance, a peak near 2200 cm⁻¹ could indicate a C≡C or C≡N triple bond, while peaks near 1500-1600 cm⁻¹ might suggest aromatic C=C stretches.

Eliminate compounds that do not have functional groups corresponding to the observed peaks in the IR spectrum. Narrow down the options by systematically ruling out mismatches.

Once you have identified the compound that matches all the key peaks in the IR spectrum, verify your choice by ensuring that no other compound fits the spectrum as well. This will confirm the correct answer.

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Key Concepts

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

Infrared Spectroscopy (IR)

Infrared spectroscopy is a technique used to identify functional groups in organic compounds by measuring the absorption of infrared light. Different bonds absorb characteristic frequencies of IR radiation, resulting in a spectrum that can be analyzed to determine the presence of specific functional groups, such as alcohols, carbonyls, and amines.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Understanding common functional groups, such as hydroxyl (-OH), carbonyl (C=O), and carboxyl (-COOH), is essential for interpreting IR spectra, as each group has distinct absorption peaks.

Spectrum Interpretation

Interpreting an IR spectrum involves analyzing the peaks and their corresponding wavenumbers to deduce the molecular structure of a compound. Peaks indicate the presence of specific functional groups, and their intensity and position can provide insights into molecular interactions and the environment of the functional groups.

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Related Practice

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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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

Each of the IR spectra shown below is accompanied by a set of four compounds. In each case, indicate which of the four compounds is responsible for the spectrum.

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Textbook Question

Five compounds are shown for each of the IR spectra below. Indicate which of the five compounds is responsible for each spectrum.

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Textbook Question

Each of the IR spectra shown below is the spectrum of one of the following compounds. Identify the compound that produced each spectrum.

a. <IMAGE>

Textbook Question

Each of the IR spectra shown below is the spectrum of one of the following compounds. Identify the compound that produced each spectrum.

b. <IMAGE>

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

Key Concepts

Infrared Spectroscopy (IR)

Functional Groups

Spectrum Interpretation

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

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