ORG-CHEM-LEC-CIP Rev1

1-Phenylethanol
Mirabella Anne F. Odtohan, Chastney Rois M. Olesco, Pamela Marie G. Pampilon, and Alexandra Estelle
C. Pineda
Department of Biochemistry, Faculty of Pharmacy, University of Santo Tomas
Figure 1. 1-Phenylethanol
I. IR Spectra
Infrared spectroscopy (IR) is used to identify the functional groups of a substance. It deals with
the infrared region of the electromagnetic spectrum. This spectroscopic technique exploits the
molecule’s ability to absorb specific frequencies innate to their structure [1]. The frequencies absorbed
by the functional groups signify the transition energy required to vibrate the bond.
Figure 2. IR Spectra of 1-Phenylethanol
The IR spectra showed a broad band between 3400 cm-1 and 3200 cm-1, and a stretch at around
1300 cm-1 and 1000 cm-1 which indicated the presence of an alcohol group. Furthermore, it exhibited
medium peaks from 1400 cm-1 to 1600 cm-1 and beyond the 3000 cm-1, which suggested the existence of
alkene groups from an aromatic compound. An overtone at around 1600 cm -1 supported the inference
as well. Medium peaks were displayed around 1500 cm-1 to 1300 cm-1, indicative of an alkane group.
II. Mass Spectrum
Mass spectrometry (MS) is a spectroscopic technique used in identifying the molar weight and
molecular formula of an organic compound. Molecules undergo a process called ionization via the
beams of high-energy electrons, forming a species referred to as a radical cation (M+●). The radical
cation eventually breaks off into fragments as it is unstable, and the cations from the fragmentation
process are responsible for the peaks found in a mass spectrum graph.
Figure 3. Mass Spectrum of 1-Phenylethanol
As seen in Figure 3, an unknown compound identified as 1-Phenylethanol shows prominent

peaks at 77m/z, 78m/z, 79m/z, 104m/z, and 107m/z. 104m/z represents the base peak and the
molecular ion peak is found at 122m/z. The molecular formula (C8H10O) has an IHD value of 4, indicative
of the benzene ring. The smaller M-1 peak further supports the presence of the aforementioned
compound, resulting from the loss of a hydrogen atom from the aromatic ring. As benzene is substituted
in the case of 1-Phenylethanol, it would undergo a fragmentation process called alpha cleavage which
would then be followed by hydrogen rearrangement. The ethanol group would first be cleaved from the
ring, producing the 77m/z peak (C6H5+). The hydrogen atoms would then rearrange to form peaks 78m/z
(C6H6+) and 79m/z (C6H7+). Peak 79m/z is also obtainable from the spontaneous rearrangement of
cleaving of the tropylium ion. The base peak, 104m/z, occurs via dehydration of the alcohol group to
form an alkene attached to the ring with water as a by-product. 107m/z is obtained from the cleaving of
the methyl group.
III. H-1 NMR

Nuclear magnetic resonance (NMR) spectroscopy is a technique used to characterize organic
molecules by identifying carbon-hydrogen frameworks within an organic compound. H-NMR was the
first and most common atom used in nuclear magnetic resonance spectroscopy. The atomic nucleus, a
spinning charged particle, generates a magnetic field. The spins of the magnetic nuclei are oriented
randomly in the absence of an external applied magnetic field. However, when an external magnetic
field is present, the nuclei adopt specific orientations either with or against the field of the external
magnet.
Figure 4. H-1 NMR of 1-Phenylethanol
Figure 4 shows the H-NMR spectra for the unknown compound. Table 1 shows the summary of
the data needed to identify the unknown. The chemical shift at 1.5 ppm which has a duplet splitting has
3 hydrogens which is most likely a methyl group with a neighboring carbon with only 1 hydrogen
attached to it. Then, the chemical shift at 3.4 ppm with a singlet splitting has 1 hydrogen that is attached
to an atom without a hydrogen. Moving on, the chemical shift at 4.9 ppm with a quartet splitting has
also 1 hydrogen and may be attached to a methyl group. The chemical shift at 7.4 ppm and the multiplet
splitting most likely correlates to a benzene ring. Analyzing the data given and fitting each piece
together, a possible structure, 1-phenylethanol, is proposed.
Chemical Shift Splitting Integration # of H
1.5 ppm duplet 2.2 3
3.4 ppm singlet 0.7 1
4.9 ppm quartet 0.7 1
7.4 ppm multiplet 3.6 5

Table 1. H-NMR data for 1-Phenylethanol
IV. C-13 NMR
Another type of NMR is the Carbon-13 NMR, which sheds light on the different types of carbons
found within an organic compound. Carbon-12 atoms lack a nuclear spin, hence do not create signals in
an NMR spectrum. For this reason, only Carbon-13 atoms are observed, and because it has a low natural
abundance unlike the proton NMR, there is normally no coupling between adjacent carbon atoms [3].
The Hebrew University of Jerusalem states that Carbon-13 that yields sharp signals and have wide
chemical shift ranges due to the fact that is a low sensitive nucleus[2].
Figure 5. C-13 NMR Spectrum of 1-Phenylethanol
Figure 5 depicts the Carbon-13 NMR for 1-Phenylethanol. The benzene ring, with a
chemical shift ranging from 110ppm to 175ppm, is denoted by the tall peaks at 128ppm, 127ppm, and
125ppm. These peaks are also indicative of a double bond (110ppm-140pp). A Carbon-Oxygen bond is
also showcased at 70ppm. A deshielded peak at 25ppm represents the methyl group.
REFERENCES:
[1] Shikha, D. & Awasthi, R. (2015). Application of I.R. Spectroscopy & Mass Spectrometry in
Structural Elucidation of Drugs. International Journal of Advanced Research in Chemical Science
(IJARCS), 2 (8), 38-45.
[2] University Hebrew of Jerusalem. (n.d.). Carbon-13 NMR. Retrieved from Institute of Chemistry:
http://chem.ch.huji.ac.il/nmr/techniques/1d/row2/c.html
[3] University of Puget Sound. (n.d.). Introduction to Carbon NMR. Retrieved from University of Puget
Sound: http://www2.ups.edu/faculty/hanson/Spectroscopy/NMR/CNMR.htm
National Center for Biotechnology Information. PubChem Database. 1-Phenylethanol, CID=7409,
https://pubchem.ncbi.nlm.nih.gov/compound/1-Phenylethanol (accessed on Dec. 11, 2019)
McMurry, J. E. (9th Edition). (2019). Organic Chemistry. Boston, MA, USA: Cengage Learning

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1-Phenylethanol

Figure 2. IR Spectra of 1-Phenylethanol

Figure 3. Mass Spectrum of 1-Phenylethanol

As seen in Figure 3, an unknown compound identified as 1-Phenylethanol shows prominent

III. H-1 NMR

Figure 4. H-1 NMR of 1-Phenylethanol

Chemical Shift Splitting Integration # of H

1.5 ppm duplet 2.2 3

3.4 ppm singlet 0.7 1

4.9 ppm quartet 0.7 1

7.4 ppm multiplet 3.6 5

Figure 5. C-13 NMR Spectrum of 1-Phenylethanol

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