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

Mass Spect:Fragmentation

Organic Chemistry

15. Analytical Techniques:IR, NMR, Mass Spect

Mass Spect:Fragmentation

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Problem 7

Textbook Question

Propose a fragmentation to account for each numbered peak in the mass spectrum of n-butyl isopropyl ether.
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Identify the molecular structure of n-butyl isopropyl ether. It consists of a butyl group (C4H9) attached to an oxygen atom, which is further connected to an isopropyl group (C3H7). The molecular formula is C7H16O.

Understand the process of fragmentation in mass spectrometry. Fragmentation occurs when the molecule is ionized, leading to the breaking of bonds and the formation of smaller ionized fragments. These fragments correspond to the peaks in the mass spectrum.

Propose a fragmentation pathway for the first peak. A common fragmentation involves the cleavage of the bond between the oxygen atom and the butyl group, resulting in a butyl cation (C4H9⁺) and an isopropoxy radical (C3H7O•). The mass of the butyl cation can be calculated as follows: \( \text{C}_4\text{H}_9^+ \) = \( 4(12.01) + 9(1.008) \).

Propose a fragmentation pathway for the second peak. Another possible fragmentation involves the cleavage of the bond between the oxygen atom and the isopropyl group, resulting in an isopropyl cation (C3H7⁺) and a butoxy radical (C4H9O•). The mass of the isopropyl cation can be calculated as follows: \( \text{C}_3\text{H}_7^+ \) = \( 3(12.01) + 7(1.008) \).

Analyze additional peaks by considering secondary fragmentations or rearrangements. For example, the butyl cation (C4H9⁺) can undergo further fragmentation to form smaller ions such as the ethyl cation (C2H5⁺) or propyl cation (C3H7⁺). Similarly, the isopropyl cation (C3H7⁺) can fragment further to form smaller ions. Calculate the masses of these smaller ions to match them with the peaks in the spectrum.

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Key Concepts

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

Mass Spectrometry

Mass spectrometry is an analytical technique used to measure the mass-to-charge ratio of ions. It involves ionizing chemical species and sorting the ions based on their mass. The resulting mass spectrum displays peaks corresponding to different ions, where the height of each peak indicates the relative abundance of each ion. Understanding mass spectrometry is crucial for interpreting the fragmentation patterns of compounds.

Fragmentation Patterns

Fragmentation patterns refer to the specific ways in which a molecule breaks apart into smaller ions during mass spectrometry. These patterns are influenced by the molecular structure and the stability of the resulting fragments. Analyzing fragmentation helps in identifying the structure of the original compound, as each peak in the mass spectrum corresponds to a specific fragment formed during ionization.

n-Butyl Isopropyl Ether Structure

n-Butyl isopropyl ether is an organic compound with a specific structure that influences its fragmentation behavior. It consists of a butyl group (C4H9) and an isopropyl group (C3H7) connected by an ether linkage (R-O-R'). Understanding the molecular structure is essential for predicting how the compound will fragment under ionization, which directly relates to the peaks observed in its mass spectrum.

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In the mass spectrum of hexan-3-ol, identify the fragments arising from two α-cleavage fragmentations and one dehydration fragmentation.

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For each of the molecules shown, predict the structure of at least one major fragment in the mass spectrum.

(d)

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Propose a fragmentation to account for each numbered peak in the mass spectrum of n-butyl isopropyl ether.<IMAGE>

Key Concepts

Mass Spectrometry

Fragmentation Patterns

n-Butyl Isopropyl Ether Structure

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Propose a fragmentation to account for each numbered peak in the mass spectrum of n-butyl isopropyl ether.
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