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Mass Spectrometry Basics for Organic Chemistry

Reading the molecular ion, isotope peaks, and fragmentation.

Quick answer Electron ionization makes a radical cation M+• whose m/z is the molecular weight; excess energy breaks weak bonds into fragment cations, the tallest being the base peak (100%). Read structure from M+•, the base peak, neutral losses (−15, −18, −28, −29), isotope patterns (Cl gives M+2 ≈ ⅓, Br gives M+2 ≈ M), and the nitrogen rule.

Unlike IR or NMR, MS does not measure absorption — it weighs individual ions to give the molecular weight and a map of where the molecule breaks apart.

Ethanol · M = 46
Acetone · M = 58
Bromoethane · M = 108/110

The three questions MS answers — molecular weight, fragmentation, and isotope pattern — in one glance. Structures drawn live.

1. MS Weighs the Molecule and Its Fragments

In electron ionization, ~70 eV electrons knock one electron out to form the radical cation M+•, which is sorted by mass-to-charge ratio (m/z); since almost every ion is +1, m/z is effectively mass, and only cations are ever detected.

Methane · M+• at m/z 16
Butane · M+• at m/z 58

2. The Molecular Ion (M+•) Gives the Molecular Weight

M+• is the rightmost significant peak and equals the molecular weight, but easily-fragmented molecules (branched alkanes, alcohols) can make it tiny or absent.

Diethyl ether · M+• = 74
Acetic acid · M+• = 60

3. The Base Peak Is the Most Stable Fragment

The base peak is the tallest bar (set to 100%) and marks the most stable cation — for acetone, the resonance-stabilized acylium ion CH3–C≡O+ at m/z 43.

Acetone → acylium at m/z 43 (base peak)
Toluene (M=92) → benzylic cation m/z 91

4. Weak Bonds Break to Give the Most Stable Cation

Fragmentation follows carbocation stability (3° > 2° > 1°, plus allylic/benzylic/acylium resonance), so M+• ejects a small neutral to give a peak at (M − loss) — a handful of losses cover most spectra:

2-Methylbutane (M=72) → M−15
Propanal (M=58) → M−29 (loss of CHO)
LossNeutral lostPoints to
M − 15•CH3 (methyl radical)a methyl branch
M − 17•OH (hydroxyl radical)alcohol / carboxylic acid
M − 18H2O (water)alcohol
M − 28CO (carbon monoxide)carbonyl
M − 29•CHO or •C2H5aldehyde or ethyl group
M − 45•COOH or •OC2H5carboxylic acid or ester

5. Isotope Peaks Reveal Chlorine and Bromine

Heavier minor isotopes make small M+1/M+2 peaks whose relative heights fingerprint the halogens:

Chloroethane · M+2 ≈ ⅓ (64/66, 3:1)
Bromoethane · M+2 ≈ M (108/110, 1:1)
M+2 : M ratioIsotope signatureConclusion
≈ 1 : 3 (33%)35Cl / 37Clone chlorine present
≈ 1 : 1 (98%)79Br / 81Brone bromine present
tiny M+1 only13C (1.1% × n)counts carbon atoms

6. The Nitrogen Rule Counts Nitrogens from the Parity of M

An odd-mass M+• means an odd number of nitrogens; an even mass means zero or an even number — because nitrogen alone has even mass but odd valence.

Methylamine · odd M = 31 → one N
Pentane · even M = 72 → no N

7. Summary

M+• = molecular weight (rightmost peak) · base peak (100%) = most stable fragment · neutral losses −15/−18/−28/−29/−45 · M+2 ≈ ⅓ → Cl, M+2 ≈ M → Br · odd M → nitrogen · combine with degrees of unsaturation and IR.

Worked example

Problem. A compound gives a molecular ion at m/z 46 and a strong fragment at m/z 31. Propose a structure.
ethanol
  1. M+ = 46 fits the formula C2H6O.
  2. Losing 15 (46 → 31) means loss of a •CH3 radical.
  3. m/z 31 is the resonance-stabilised CH2=OH+ oxocarbenium from α-cleavage of ethanol.

Answer. Ethanol (CH3CH2OH): M+ 46, fragment 31 from loss of •CH3.

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Bromine. The 79Br/81Br isotopes are nearly 1:1, so one bromine gives an M+2 peak about equal in height to M (e.g. bromoethane at 108/110).

It is the acylium ion CH3–C≡O+ (loss of a •CH3 radical, M−15). It is resonance-stabilized across the C≡O+, making it the most stable — and therefore most abundant — cation.

By the nitrogen rule, an odd-mass molecular ion means an odd number of nitrogen atoms — most likely one nitrogen in the molecule.

Water (H2O). An M−18 loss is the signature dehydration of alcohols; you may also see M−17 from loss of •OH.

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