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Chloromethane Mass Spectrum Analysis

The document outlines fragmentation patterns observed in mass spectrometry for various organic compounds, including straight-chain and branched-chain alkanes, haloalkanes, aromatic compounds, aldehydes, ketones, and carboxylic acids. It provides specific examples with molecular ions and resulting carbocations for each type of compound, highlighting the stability of different carbocation types. Additionally, it includes isotope information for haloalkanes, emphasizing their relative abundances.

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18 views7 pages

Chloromethane Mass Spectrum Analysis

The document outlines fragmentation patterns observed in mass spectrometry for various organic compounds, including straight-chain and branched-chain alkanes, haloalkanes, aromatic compounds, aldehydes, ketones, and carboxylic acids. It provides specific examples with molecular ions and resulting carbocations for each type of compound, highlighting the stability of different carbocation types. Additionally, it includes isotope information for haloalkanes, emphasizing their relative abundances.

Uploaded by

s1920068
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd

Appendix ‒ Fragmentation Patterns

1. Straight-chain alkanes

● e.g. Mass spectrum of hexane, C6H14

[CH3CH2CH2CH2---CH2CH3]•+  CH3CH2CH2CH2+ + •CH2CH3


molecular ion (m/e= 86) butyl ion (m/e = 57)

[CH3CH2CH2---CH2CH2CH3]•+  CH3CH2CH2+ + •CH2CH2CH3


molecular ion (m/e= 86) propyl ion (m/e = 43)

[CH3CH2---CH2CH2CH2CH3]•+  CH3CH2+ + •CH2CH2CH2CH3


molecular ion (m/e= 86) ethyl ion (m/e = 29)

[CH3---CH2CH2CH2CH2CH3]•+  CH3+ + •CH2CH2CH2CH2CH3


molecular ion (m/e= 86) methyl ion (m/e = 15)

Appendix ‒ Fragmentation Patterns 1


2. Branch-chain alkanes

● e.g. Mass spectrum of methylbutane

 +

molecular ion (m/e= 72) secondary carbocation


(m/e = 57)

 +

molecular ion (m/e= 72) secondary carbocation


(m/e = 43)

 +

molecular ion (m/e= 72) primary carbocation


(m/e = 29)

Appendix ‒ Fragmentation Patterns 2


● e.g. Mass spectrum of dimethylpropane

 +

molecular ion (m/e= 72) tertiary carbocation


(m/e = 57)

 Stability of carbocation:

> >

tertiary carbocation secondary carbocation primary carbocation

Appendix ‒ Fragmentation Patterns 3


3. Haloalkanes

● e.g. Mass spectrum of iodomethane (CH3I)

Only one stable isotope: 127I

● e.g. Mass spectrum of bromomethane (CH3Br)

Isotope Relative abundance


79
Br 50.54%
81
Br 49.46%

Appendix ‒ Fragmentation Patterns 4


● e.g. Mass spectrum of chloromethane (CH3Cl)

Isotope Relative abundance


35
Cl 75.53%
37
Cl 24.47%

Appendix ‒ Fragmentation Patterns 5


4. Aromatic compounds

● e.g. Butylbenzene

 +

molecular ion (m/e= 134) Benzylic cation (m/e = 91)

5. Aldehydes and Ketones

● e.g. Butanone

Appendix ‒ Fragmentation Patterns 6


6. Carboxylic acids and Acid Derivatives (e.g. Esters & Amides)

● e.g. Mass spectrum of benzoic acid

 C6H5CO+ + •OH

molecular ion (m/e= 122) (m/e = 105)

 C6H5+ + •COOH

molecular ion (m/e= 122) (m/e = 77)

Appendix ‒ Fragmentation Patterns 7

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