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

Previous problemNext problem

3:14 minutes

Problem 69

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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Verified step by step guidance

Step 1: Understand the reaction. Nitrile hydrolysis involves converting a nitrile group (R-C≡N) into a carboxylic acid (R-COOH) using water and heat. The reaction typically requires acidic or basic conditions and sufficient heat to proceed.

Step 2: Consider the role of IR spectroscopy. Infrared (IR) spectroscopy is used to identify functional groups in a compound based on the absorption of infrared light at specific wavelengths. Each functional group has characteristic absorption bands.

Step 3: Identify key IR absorption bands. For nitriles, the C≡N stretch typically appears around 2210-2260 cm⁻¹. For carboxylic acids, the C=O stretch appears around 1700-1750 cm⁻¹, and the O-H stretch appears broadly around 2500-3300 cm⁻¹.

Step 4: Analyze the IR spectrum of the product. Check for the disappearance of the nitrile peak and the appearance of the carboxylic acid peaks. The presence of a strong C=O stretch and a broad O-H stretch would indicate successful conversion to a carboxylic acid.

Step 5: Conclude based on IR data. If the IR spectrum shows the expected carboxylic acid peaks and the nitrile peak is absent, the hypothesis that ambient heat was sufficient for the reaction is supported. Otherwise, further investigation is needed.

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Key Concepts

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

Nitrile Hydrolysis

Nitrile hydrolysis is a chemical reaction where a nitrile is converted into a carboxylic acid. This process typically requires acidic or basic conditions and heat to proceed efficiently. Understanding the mechanism involves recognizing the nucleophilic attack on the carbon of the nitrile group, leading to the formation of an amide intermediate, which further hydrolyzes to yield the carboxylic acid.

Infrared (IR) Spectroscopy

IR spectroscopy is an analytical technique used to identify functional groups in a molecule by measuring the absorption of infrared light at different wavelengths. Each functional group, such as nitriles or carboxylic acids, has characteristic absorption bands. For instance, nitriles show a sharp peak around 2250 cm⁻¹, while carboxylic acids exhibit broad peaks around 2500-3300 cm⁻¹ due to O-H stretching.

Effect of Temperature on Reaction Rate

Temperature is a critical factor influencing the rate of chemical reactions. Higher temperatures generally increase reaction rates by providing the necessary energy to overcome activation barriers. In the context of the nitrile hydrolysis, ambient heat from a non-air-conditioned environment might be sufficient to drive the reaction, depending on the specific energy requirements of the process.

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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

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

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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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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