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5-26-1947
Synthesis of Terpenes
Jeanetta Reneberger
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Synthesis of Terpenes
Jeiinetta Reneberger Department Honors Ursinus College May, 1947
This paper is submitted in partial fulfillment of Department Honors.
Group Adviser Introdxiction
Terpenes are organic compounds having the empirical formula (Q.Hji) , They are the essential oils which early chemists extracted from the leaves, flowers, resins, bark, and roots of many plants. These volatile perfume materials were called the "essence". Isoprene, obtained by distillation of caoutchouc (india rubber), is the -narent hydrocarbon from which all terpenes are derived. Many plants produce isoprene and condense it through either linear or cyclic polymerization into terpene compounds. These in turn oxidize, hydrolize, or reduce to form many familiar products. A few terpenes are solids, hut most are volatile liquids^having boiling points between 155** smd 1R5°. They are §^'^^Mft from their natural soiirces by steam distillation and by extraction with organic solvents. Terpenes incliide both open chain compounds and cyclic compounds having one and tvro rings. They are very active sub• stances, and have a complex chemistry. Addition react'-ons are common, for they are generally unsaturated; they polymerize readily. Terpenes are easily oxidized; they combine with ozone, and show the general characteristics of compounds containing double bonds. All terpenes are practically insoluble in water, but they are readily soluble in the ordinary organic solvents. Many industrial products are made from terpenes and their derivatives. They are used extensively in perfumes, flavors, paints, varnishes, plastics, and medicines. Terpenes are of great use in chemical study, for they form the link between simple organic structures and complex natural products. Classification
All terpenes have the empirical formxila CoHn- or some multiple of it, Hemiterpenes have the empirical formula G^Eg, They include the parent of all terpenes, Isoprene
C M,. = CM CH -Chi.
The true terpenes of formula C,^H,^are represented by
terpin
sylvestrene CM,
MC ^-«-^^..„3
Sesquiterpenes, having the formula C,^ H^,, inclixde
farnesol CH^CH^ T-'CH *H^CH^ T'CH^HX* »^
nerolidol CH, ^^H^^H^
Diterpenes, having the empirical formula, C ^.^fL ^j^, include among their representatives the common compovmd vitamin A -'^'^ i^^tMCH^cni^CMeH.oH H,C c Polyterpenes, which contain 25 or more carbons, are represented
crt '""^ "^"^ squalene ^ • AH.H.C- CH CH, CH,.: = en JH.
«H C = CHCH^CH.C = t MCM^cHjC = cHcHi ^ cHj CH,
carotene ^M, ,CH,
^'^ . ,„e.= CHCH--CM e - tHCH=CMCH ^CCH=\