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TERPENES

TERPENES. natural rubber. head. . D. C. tail. C. C. C. C C. C. C. C. C. isoprene. isoprene unit. TERPENES. The Czech chemist Leopold Ruzicka ( born 1887) showed that many compounds found in nature were formed from multiples

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TERPENES

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  1. TERPENES

  2. natural rubber head . D C tail C C C C C C C C C isoprene isoprene unit 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”.

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

  4. Head-to-Tail an extra bond . Head-to-Tail C Tail-to-Tail C C C C The terms head-to-tail and tail-to-tail are often used to describe how the isoprene units are joined. JOINING ISOPRENE UNITS

  5. limonene from lemon and orange peels TERPENES CAN BE SHOWN TO BE FORMED FROM ISOPRENE UNITS 7 1 2 6 head to tail 5 3 4 9 10 8 diagram showing how two isoprene units combine to form the limonene skeleton

  6. 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 eight C40 tetraterpene NOTE: hemi = half di = two sesqui = one and a half tri = three tetra = four

  7. SOME TERPENES (C10) geraniol menthol rose and other flowers peppermint camphor a-pinene camphor tree turpentine

  8. SESQUITERPENES guaiazulene geranium oil caryophyllene oil of cloves

  9. ….. more sesquiterpenes cedrene cedar wood oil longifolene pine species

  10. C H 3 C H C H 3 O H 3 C H 3 C H 3 C H C H 3 3 ambrein ambergis TRITERPENES

  11. head-to-tail tail-to-tail head-to-tail b-carotene carrots TETRATERPENE

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