spectrum (can be printed in landscape orientation). Loss of water from this gives a m/z=41 fragment, and loss of ethene from m/z=59 gives a m/z=31 fragment. that these items are necessarily the best available for the purpose. Phenol, 3-methyl- Formula: C 7 H 8 O Molecular weight: 108.1378 IUPAC Standard InChI: InChI=1S/C7H8O/c1-6-3-2-4-7 (8)5-6/h2-5,8H,1H3 IUPAC Standard InChIKey: RLSSMJSEOOYNOY-UHFFFAOYSA-N CAS Registry Number: 108-39-4 Chemical structure: This structure is also available as a 2d Mol file or as a computed 3d SD file ), Virtual Textbook of Organic Chemistry. The most abundant ion of the molecule under mass 3-Pentanol shows three significant fragment ions. The base peak is from the C-C cleavage adjacent to the C-N bond. The nature of the fragments often provides a clue to the molecular structure, but if the molecular ion has a lifetime of less than a few microseconds it will not survive long enough to be observed. been selected on the basis of sound scientific judgment. NIST subscription sites provide data under the Institute of Standards and Technology, nor is it intended to imply Phenol | C6H5OH or C6H6O | CID 996 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. Accessibility Statement For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. These peaks will have splitting typical for aromatic protons. If you look at the structure of pentan-3-one, it's impossible to get that particular fragment from it. In the mass spectrum of the molecule phenol, C 6 H 5 OH, the approximate intensity of the peak at m/z 95, relative to the molecular ion at 94 will be which of the following? A complex reaction (from the internet), mass change 94 - The product ions are the same as with APCI shown in Figure 2. The fragments of a molecule cause a unique pattern in the mass spectrum.These reactions are well documented over the decades and fragmentation pattern is useful to determine the molar weight and structural . available from the NIST/EPA/NIH Mass Spectral Library. 2. ), can dramatically alter the fragmentation pattern of a compound. The integration values of each group of signals is given on the spectrum. Mass Spectra Fragmentation Patterns The fragmentation of molecular ions into an assortment of fragment ions is a mixed blessing. errors or omissions in the Database. equations to explain the most abundant ion peaks of phenol Different sources quote totally different chemical shifts for the hydrogen atom in the -OH group in alcohols - often inconsistently. Please see the following for information about Protons on carbon adjacent to the alcohol oxygen show up in the region of 3.4-4.5 ppm. of fragmentation ions in the mass spectrum of phenol, how to analyse the mass Select a region with data to zoom. box], Interpreting the mass The m/z = 29 peak is produced by the ethyl ion - which once again could be formed by splitting the molecular ion either side of the CO group. The reaction productsfrom 2,4-dichlorophenol were tetrachloro-phenoxyphenols and tetrachlorodihydroxybiphenyls (Figure 5), as determined from their mass spectraand those of their methyl ethers. Accessibility Statement For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. describe the two most common initial fragmentations in the mass spectra of alcohols. available from the NIST/EPA/NIH Mass Spectral Library. The base peak is the tallest peak because it represents the commonest fragment ion to be formed - either because there are several ways in which it could be produced during fragmentation of the parent ion, or because it is a particularly stable ion. This peak in 2-methylbutane is caused by: The ion formed is a secondary carbocation - it has two alkyl groups attached to the carbon with the positive charge. It is commonly used for the identification of organic compounds from electron ionization mass spectrometry. We'll look at two common examples of this. ), Virtual Textbook of Organic Chemistry. 29 = 65. You will find a link at the bottom of the page. There can't be 5 because 5 x 12 = 60. William Reusch, Professor Emeritus (Michigan State U. Given the following 1H NMR spectrum, draw the structure. Loss of water from this gives a m/z=41 fragment, and loss of ethene from m/z=59 gives a m/z=31 fragment. This section will ignore the information you can get from the molecular ion (or ions). a) 1 The other carbons in the phenol ring appear in the region typical for aromatic carbons of 125-150 ppm. Protons directly attached to the alcohol oxygen often appear in the region of 2.0 to 2.5 ppm. Unless the alcohol is absolutely free of any water, the hydrogen on the -OH group and any hydrogens on the next door carbon don't interact to produce any splitting. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. This page looks at how fragmentation patterns are formed when organic molecules are fed into a mass spectrometer, and how you can get information from the mass spectrum. The LibreTexts libraries are Powered by NICE CXone Expert and are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. Keywords: CO neutral loss; Fragmentation; density functional theory; intrinsic reaction coordinates calculation; nudged elastic band method; p-benzoquinone; phenol; synchronous transit . You can often predict what peaks will be observed in the mass spectrum simply by looking at a molecule's structure and seeing which . Alcohols, ethers and highly branched alkanes generally show the greatest tendency toward fragmentation. 3-Phenyl-2-propenal (C9H8O) with MW = 132.16. From mass spectroscopy analysis it was determined that a compound has the general formula C3H8O. describe the characteristic feature of the proton NMR spectra of alcohols and phenols. Given the following 1H NMR spectrum, draw the structure. This is very confusing! A split producing a tertiary carbocation will be more successful still. click the mouse on the plot to revert to the orginal display. phenol Chemistry Notes, Scroll down and take Mass spectral fragmentation of the [M − H] − ion of 2-isopropyl phenol using electrospray ionization in negative ion mode. by the U.S. Secretary of Commerce on behalf of the U.S.A. You may use tables of characteristic absorptions as an aid to accomplishing this objective. Ionized Phenol and Cyclohexa-1,3-dien-5-one (ortho-Isophenol) Generated by Fragmentation of Precursor Ions The Radical Cations of ortho-Isophenol. Another example is a secondary amine shown below. \[M^{\cdot +} \rightarrow X^+ + Y^{\cdot}\]. by the U.S. Secretary of Commerce on behalf of the U.S.A. ), Virtual Textbook of Organic Chemistry. 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