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Farnesol - Structure Elucidation, Lecture notes of Organic Chemistry

Chaudhary Devi Lal UniversityOrganic Chemistry

Structure of Farnesol, structure elucidation, synthesis

Typology: Lecture notes

2019/2020

Uploaded on 05/04/2020

Deepika29
Deepika29 🇮🇳

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Farnesol
HOH2C
• Acyclicsesquiterpenoidasithave3isopreneunits.
• Occursintheoilofambretteseeds,rose,citronellaetc.
• Firstsesquiterpenoidwhosestructurewassolved.
• Liquidinnature.
• Boilingpoint‐120°C.
StructureElucidation‐
1. MolecularData‐C15H26O
2. Number of double bonds‐ On reduction with hydrogen and Bromine, Farnesol gives
hexahydrofarnesol&Farnesolhexabromide i.e.Farnesolcontains3doublebonds.
3. NatureofOxygen‐Onreactionwith Lucasreagent, itis shownthatFarnesolcontain1°OH. Itis
furtherconfirmedbyoxidation.
4. NumberofRings‐
C15H32Ocorrespondsto CnH2n+2i.e.Farnesolisacyclicandcontain3isoprene unitsso belongsto
sesquiterpenoid.
pf3

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Farnesol

HOH 2 C

  • Acyclic sesquiterpenoid as it have 3 isoprene units.
  • Occurs in the oil of ambrette seeds, rose, citronella etc.
  • First sesquiterpenoid whose structure was solved.
  • Liquid in nature.
  • Boiling point‐ 120°C.

Structure Elucidation‐

  1. Molecular Data‐ C 15 H 26 O 2. Number of double bonds‐ On reduction with hydrogen and Bromine, Farnesol gives hexahydrofarnesol & Farnesolhexabromide i.e. Farnesol contains 3 double bonds. 3. Nature of Oxygen‐ On reaction with Lucas reagent, it is shown that Farnesol contain 1°OH. It is further confirmed by oxidation. 4. Number of Rings‐

C 15 H 32 O corresponds to C (^) n H2n+2 i.e. Farnesol is acyclic and contain 3 isoprene units so belongs to sesquiterpenoid.

5. Oxidative degradation‐

C 14 H 23 CH 2 OH Farnesol

O (^) C 14 H^23 CHO^

NH 2 OH C 14 H 23 CH NOH

Ac 2 O

  • H 2 O

C 14 H 23 C N

Alkaline hydrolysis C 13 H 22 O + C 14 H 23 COOH

(I) (II)

(V) (IV) (III)

Farnesal Farnesal oxime

Ketone Farnesenic acid Farnesol nitrile

  • The ketone C 13 H 22 O was found to be identical with α,β‐dihydropseudoionone obtained from geranyl chloride and sodium acetoacetate.

Geranyl chloride

  • NaHC^

COOC 2 H 5 COCH (^3)

Sodiumacetoacetate

Cl

O

COOC 2 H 5

  1. Hydrolysis
  2. -CO 2

O

Geranyl acetone or -dihdropseudoionone

  • As we have seen that ketone C 13 H 22 O have 2 carbons less than farnesol nitrile. This must be due to presence of some α,β‐unsaturated carbonyl compound.
  • As ketone formed from Farnesol nitrile which itself is formed formed from farnesal. So above reaction shows that Farnesal must contain α,β‐unsaturated carbonyl moiety. 6. Reaction with O 3 ‐
  • Formation of these products also proves the given structure of farnesol. 7. Synthesis‐