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Alpha Terpineol
Synthesis
Submitted By: Muhammad Razzaq
Submitted To: Prof. Dr. Muhammad Zubair
Roll No: 230805
Introduction
 α-Terpineol is a monoterpene alcohol.
 It has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil.
There are four isomers, alpha-, beta-, gamma terpineol, and terpinen-4-ol. beta- and gamma
terpineol differ only by the location of the double bond.
 Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent.
Structure Elucidation
1. Molecular formula was determined as C10H18O (HDI = 02)
2. Presence of one double bond (C=C): It adds one molecule of H2 or one molecule of bromine to
form addition product, which indicate the presence of one carbon-carbon double bond.
3. It does not give aldehyde or ketone on mild oxidation and can be dehydrated to limonene.
Hence the alcoholic group should be tertiary
Continue…..
4. The fully saturated hydrocarbon corresponds to α terpineol is C10H20. Therefore it should
be monocyclic mono-terpenoid tertiary alcohol.
5. When treated with conc. H2SO4 it gives p-cymene.
Structure Elucidation
6. Position of double bond was found out by Graded oxidation reactions
Structure Elucidation
7. Position of tertiary alcohol group.
Wallach Graded Oxidation
1. From Citral
Synthesis of Alpha Terpineol
2. From p-Toluic Acid
3. From Alpha Pinene
4. From Terpin
5. From Diel Alder Reaction
Spectroscopic
Characterization
IR Spectroscopy
H-NMR Spectrum
C-NMR
Mass Spectrum
Applications
1. Alpha-Terpineol plays an important role in the industrial field because it has a pleasant odour similar
to lilacs and it is a common ingridient in perfumes, cosmetics, and aromatic scents.
2. Biological Properties:
Companies using Terpineol as Cosmetics
References
 https://www.acs.org/molecule-of-the-week/archive/t/alpha-terpineol.html#:~:text=
%CE%B1%2DTerpineol%20is%20a%20terpene,of%20terpin%2C%20a%20terpene%20diol.
 https://www.slideshare.net/DrSSreenivasa/chemistry-of-terpineol
 Synthesis of terpineol from α-pinene by homogeneous acid catalysis – ScienceDirect
 Two-step continuous flow synthesis of α-terpineol – ScienceDirect
 https://courseware.cutm.ac.in/wp-content/uploads/2020/05/Lecture_structure_of-
a_terpineol.pdf
 https://www.tsijournals.com/articles/the-diels-alder-reactionfmo-and-stepwise-rad
ical-ion-cycloaddition-pathways-13946.html
 Chemistry of α-Terpineol | PPT (slideshare.net)
 (PDF) α-Terpineol, a natural monoterpene: A review of its biological properti
es (researchgate.net)
 https://webbook.nist.gov/cgi/inchi?ID=C98555&Type=IR-SPEC&Index=1
 https://www.chemicalbook.com/SpectrumEN_98-55-5_13CNMR.htm
 https://www.researchgate.net/figure/Mass-spectrum-of-a-Terpineol-with-
Retention-Time-RT-5948_fig4_306308930
Thanks !

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Terpineol and it's characterization pptx