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Chapter 14: Problem 10

What rule would you expect for the \(m / z\) values of fragment ions resulting from the cleavage of one bond in a compound with an odd number of nitrogen atoms?

Short Answer

Expert verified
Answer: The m/z values for the resulting fragment ions will be either both odd or both even. This rule ensures that the sum of the nominal masses of the two fragment ions is still an odd value, maintaining the original compound's nitrogen count and mass value.

Step by step solution

01

Understanding the Nitrogen Rule

The nitrogen rule is a simple rule that states that a compound containing an odd number of nitrogen atoms has an odd nominal mass, while a compound containing an even number of nitrogen atoms has an even nominal mass.
02

Determining the Mass of the Fragment Ions

Fragment ions are formed by breaking a bond within the compound, which results in smaller charged species. When a bond is cleaved, each fragment ion will inherit a portion of the compound's structure, including nitrogen atoms.
03

Applying the Nitrogen Rule to the Fragment Ions

Since the original compound has an odd number of nitrogen atoms and an odd nominal mass, we need to predict the m/z values for fragment ions after cleaving one bond. By virtue of the nitrogen rule, any fragment ions produced will have one of the following combinations of nitrogen atoms: 1. Odd number of nitrogen atoms -> Odd nominal mass 2. Even number of nitrogen atoms -> Even nominal mass When the bond is cleaved, the number of nitrogen atoms in the two portions will be either both odd or both even. This is essential for the mass rule conservation.
04

The Rule for m/z Values of Fragment Ions

Taking into account the nitrogen rule and the conservation of mass, we can derive a rule for the m/z values of fragment ions resulting from the cleavage of one bond in a compound with an odd number of nitrogen atoms: The m/z values for the resulting fragment ions will be either both odd or both even. This rule ensures that the sum of the nominal masses of the two fragment ions is still an odd value, maintaining the original compound's nitrogen count and mass value.

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Most popular questions from this chapter

Carboxylic acids often give a strong fragment ion at \(m / z(\mathrm{M}-17)\). What is the likely structure of this cation? Show by drawing contributing structures that it stabilized by resonance.

Draw acceptable Lewis structures for the molecular ion (radical cation) formed from the following molecules when each is bombarded by high-energy electrons in a mass spectrometer. a. b. c. d.

Write molecular formulas for the five possible molecular ions of \(\mathrm{m} / z 100\) containing only the elements \(\mathrm{C}, \mathrm{H}, \mathrm{N}\), and \(\mathrm{O}\).

Electrospray mass spectrometry is a recently developed technique for looking at large molecules with a mass spectrometer. In this technique, molecular ions, each associated with one or more \(\mathrm{H}^{+}\)ions, are prepared under mild conditions in the mass spectrometer. As an example, a protein (P) with a molecular mass of 11,812 gives clusters of the type \((\mathrm{P}+8 \mathrm{H})^{8+},(\mathrm{P}+7 \mathrm{H})^{7+}\), and \((\mathrm{P}+6 \mathrm{H})^{6+}\). At what mass-to-charge values do these three clusters appear in the mass spectrum?

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 \(\mathrm{C}_{n} \mathrm{H}_{2 n+1} \mathrm{SH}\).
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