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Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
Chapter 14, Problem 6a

Suggest possible molecular formulas for a compound that has a molecular ion with an m/z value of 86.

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Step 1: Understand the problem. The molecular ion peak in a mass spectrum corresponds to the molecular weight of the compound. The m/z value of 86 indicates the molecular weight of the compound is 86 g/mol. We need to suggest possible molecular formulas that match this molecular weight.
Step 2: Consider the general formula for hydrocarbons. Start with the simplest type of organic compounds, alkanes, which follow the formula CnH2n+2. Calculate the molecular weight for different values of n to see if it matches 86 g/mol.
Step 3: Explore other types of compounds. Consider alkenes (CnH2n) and alkynes (CnH2n-2) as possible candidates. Calculate their molecular weights for different values of n to check if they match 86 g/mol.
Step 4: Include heteroatoms. Consider the possibility of the compound containing elements like oxygen (O), nitrogen (N), or halogens (e.g., Cl, Br). Adjust the molecular formula to include these atoms and ensure the total molecular weight equals 86 g/mol.
Step 5: Verify the formulas. For each suggested molecular formula, ensure that the number of atoms and their respective atomic weights add up to 86 g/mol. Additionally, confirm that the formula adheres to the rules of valency and chemical stability.

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Key Concepts

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

Molecular Ion

A molecular ion is a charged species formed when a molecule loses or gains an electron. In mass spectrometry, the molecular ion corresponds to the intact molecule and is represented by its mass-to-charge ratio (m/z). The m/z value provides critical information about the molecular weight of the compound, which is essential for deducing possible molecular formulas.
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Empirical Formula

The empirical formula represents the simplest whole-number ratio of atoms in a compound. It is derived from the molecular formula and helps in identifying the basic composition of the molecule. For a molecular ion with an m/z value of 86, the empirical formula can guide the determination of possible molecular formulas by indicating the types and ratios of atoms present.
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Isomerism

Isomerism refers to the existence of compounds with the same molecular formula but different structural arrangements or spatial orientations. For a molecular ion with an m/z value of 86, various isomers can be proposed, each with distinct properties and reactivities. Understanding isomerism is crucial for predicting the behavior of the compound and for exploring all possible molecular formulas that fit the given m/z value.
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