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Chapter 14: Problem 16

The base peak in the mass spectrum of propanone (acetone) occurs at \(m / z 43\). What cation does this peak represent?

Short Answer

Expert verified
Answer: The cation responsible for the m/z peak at 43 in the mass spectrum of propanone is CH3CO+ (the acylium ion).

Step by step solution

01

Structure of Propanone

First, we need to know the structure of propanone. Propanone, also known as acetone, is an organic compound with the molecular formula C3H6O. Its structural formula can be written as CH3COCH3.
02

Fragmentation of Propanone

When propanone is subjected to mass spectrometry, it undergoes fragmentation to produce different cations. Various bonds within the molecule can be broken during this process, leading to the formation of different cationic species.
03

Possible fragments of Propanone

Some of the possible fragments of propanone are: 1. CH3+ (m/z = 15) 2. CH3CO+ (m/z = 43) 3. CH3CH2+ (m/z = 29)
04

Identify the cation responsible for the m/z peak at 43

We are asked to identify the fragment with an m/z ratio of 43. From the previous step, we found that CH3CO+ has an m/z ratio of 43. Therefore, the cation responsible for the base peak at m/z 43 in the mass spectrum of propanone is CH3CO+ (the acylium ion).

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Most popular questions from this chapter

The following is the mass spectrum of compound \(\mathrm{C}, \mathrm{C}_{3} \mathrm{H}_{8} \mathrm{O}\). Compound \(\mathrm{C}\) is infinitely soluble in water, undergoes reaction with sodium metal with the evolution of a gas, and undergoes reaction with thionyl chloride to give a water-insoluble chloroalkane.

The molecular ion for compounds containing only \(\mathrm{C}, \mathrm{H}\), and \(\mathrm{O}\) always has an even mass-to-charge value. Why is this so? What can you say about the mass-to-charge ratio of ions that arise from fragmentation of one bond in the molecular ion? From fragmentation of two bonds in the molecular ion?

For which compounds containing a heteroatom (an atom other than carbon or hydrogen) does the molecular ion have an even-numbered mass and for which does it have an odd-numbered mass? (a) A chloroalkane with the molecular formula \(\mathrm{C}_{n} \mathrm{H}_{2 n+1} \mathrm{Cl}\). (b) A bromoalkane with the molecular formula \(\mathrm{C}_{n} \mathrm{H}_{2 n+1} \mathrm{Br}\). (c) An alcohol with the molecular formula \(\mathrm{C}_{n} \mathrm{H}_{2 n+1} \mathrm{OH}\). (d) A primary amine with the molecular formula \(\mathrm{C}_{n} \mathrm{H}_{2 n-1} \mathrm{NH}_{2}\). (e) A thiol with the molecular formula \(\mathrm{C}_{n} \mathrm{H}_{2 n+1} \mathrm{SH}\).

The mass spectrum of compound A shows the molecular ion at \(m / z 85\), an \(\mathrm{M}+1\) peak at \(m / z 86\) of approximately \(6 \%\) abundance relative to \(\mathrm{M}\), and an \(\mathrm{M}+2\) peak at \(m / z 87\) of less than \(0.1 \%\) abundance relative to \(\mathrm{M}\). (a) Propose a molecular formula for compound \(A\). (b) Draw at least 10 possible structural formulas for this molecular formula.

Account for the presence of peaks at \(m / z 135\) and 107 in the mass spectrum of 4-methoxybenzoic acid ( \(p\)-anisic acid).
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