TERPENES

1
TERPENES
2
TERPENES
The Czech chemist Leopold Ruzicka ( born 1887)
showed that many compounds found in nature were
formed from multiples of five carbons arranged
in the same pattern as an isoprene molecule
(obtained by pyrolysis of natural rubber).
He called these compounds terpenes.
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TERPENES

1. The number of C atoms is a multiple of 5
   C5 C10 C15 C20 C25 C30 C35 C40
2. Each group of 5 C is an isoprene subunit
3. They can be saturated or unsaturated
4. Many contain O atoms as well.
5. What they all have in common is 1 2 above.

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JOINING ISOPRENE UNITS
5
TERPENES CAN BE SHOWN TO BE FORMED FROM ISOPRENE
UNITS
7
1
2
6
head to tail
3
5
4
9
8
10
diagram showing how two isoprene units combine
to form the limonene skeleton
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CLASSIFICATION OF TERPENES
TYPE OF NUMBER OF ISOPRENE TERPENE
CARBON ATOMS UNITS
one
hemiterpene
C5
two
terpene
C10
sesquiterpene
C15
three
diterpene
C20
four
triterpene
C30
six
C40
eight
tetraterpene
NOTE
hemi half di
two sesqui one and a half tri
three tetra four
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SOME TERPENES (C10)
geraniol
menthol
rose and other flowers
peppermint
a-pinene
camphor
camphor tree
turpentine
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SESQUITERPENES
guaiazulene
geranium oil
caryophyllene
oil of cloves
9
.. more sesquiterpenes
cedrene
cedar wood oil
longifolene
pine species
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TRITERPENES
11
TETRATERPENE