Islamic University in Madinah

Department of Chemistry

CHEMISTRY OF
NATURAL PRODUCTS
Prepared By
Dr. Khalid Ahmad Shadid
Chemistry Department – Islamic University in Madinah
Introduction to Natural Products
 Natural products are products from various natural sources, plants,
microbes and animals.

 Natural products can be an entire organism (e.g. a plant, an animal

or a micro-organism), a part of an organism (e.g. leaves or flowers of
a plant, an isolated animal organ), an extract of an organism or part
of an organism and an exudate, or pure compound (e.g. alkaloids,
coumarins, flavonoids, lignans, steroids and terpenoids) isolated
from plants, animals or micro-organisms.

 However, in practice, the term natural product refers to secondary

metabolites, small molecules (molecular weight < 1500 amu),
produced by an organism, but not strictly necessary for the survival
of the organism.
2
http://www.khalidshadid.com/chemistry-of-natural-products.html 3
The 18th century …
◦ At the end of the 18th century, crude drugs were still being used as powders, simple extracts,
or tinctures.

◦ The era of pure compounds (In 1803, a new era in the history of medicine)

◦ Isolation of morphine from opium

◦ Strychnine (1817)
morphine
◦ Quinine and caffeine (1820)
Nicotine Strychnine
◦ Nicotine (1828) caffeine

◦ Atropine (1833)

◦ Cocaine (1855)
Quinine
Atropine Cocaine
4
◦ In the 19th century, the chemical structures
of many of the isolated compounds were
determined

◦ In the 20th century, the discovery of

important drugs from the animal kingdom,
Captopril
particularly hormones and vitamins. In
addition, microorganisms have become a
very important source of drugs

Epibatidine

Penicillin
5
◦ Compounds from natural sources play significant roles in modern
medicine:

1. They provide a number of extremely useful drugs that

are difficult, if not impossible, to produce commercially
by synthetic means
2. Natural sources also supply basic compounds that may
be modified slightly to render them more effective or
less toxic
3. Their utility as prototypes or models for synthetic drugs
possessing physiologic activities similar to the originals

Spirea
salicylic acid Aspirin Ibuprofen 6
Overview of a bioassay-guided traditional natural product drug discovery process

Source materials Bioassay

Extract (s) Active extract (s)
(e.g. plant) Extraction
Chromatographic
fractionation

Bioassay Chromatographic
Active fraction (s)
fractions

Isolation and purification

Bioassay
Isolated compounds Active compound (s)

Identification by
spectroscopic techniques,
e.g. UV, IR, MS, NMR
Bioassay
Identified compounds Identified bioactive compound (s) 7
Terpenoids
◦ The odor of a freshly crushed mint leaf, like many plant odors, is
due to the presence in the plant of volatile C10 and C15,
compounds, which are called terpenes.

◦ Terpenoids are compounds derived from a combination of two

or more isoprene units. Isoprene is a five carbon unit,
chemically known as 2-methyl-1,3-butadiene.

◦ According to the isoprene rule proposed by Leopold Ruzicka,

terpenoids arise from head-to-tail joining of isoprene units.
Carbon 1 is called the ‘head’ and carbon 4 is the ‘tail’.

◦ For example, myrcene is a simple 10-carbon-containing

terpenoid formed from the head to-tail union of two isoprene
units as follows. 8
Classification
◦ Terpenoids are classified according to the number of isoprene units involved in the formation of these
compounds.

9
H3C CH2
C
H3C CH2
C CH2 CH
CH3 CH3 H2C CH2
H3C CH3
CH C CH2
CH CH CH
C CH C CH C CH CH C H2C CH
C CH C
H2C C CH CH CH CH CH C
H3C CH3
CH3 CH3
H2C C
CH3
CH2 CH3 -carotene
Limonene
(skin of citrus fruits)
CH3
H3C
C
CH3
CH2 CH2 CH
H2C C CH2
CH2 CH2
C
H2C CH C CH2 H2C C
C CH2 C H3C
H O
CH3 CH2

Camphor
-Selinene (Camphor tree)

10
Classification of Terpenoids
◦ Most natural terpenoid hydrocarbon have the general formula (C5H8)n. They can be classified on the
basis of value of n or number of carbon atoms present in the structure.

◦ Each class can be further subdivided into subclasses according to the number of rings present in the
structure:
i) Acyclic Terpenoids: They contain open structure.
ii) Monocyclic Terpenoids: They contain one ring in the structure.
iii) Bicyclic Terpenoids: They contain two rings in the structure.
iv) Tricyclic Terpenoids: They contain three rings in the structure.
v) Tetracyclic Terpenoids: They contain four rings in the structure. 11
A) Mono Terpenoids:
i) Acyclic Monoterpenoids ii) Monocyclic monoterpenoid

12
A) Mono Terpenoids:
◦ iii)Bicyclic monoterpenoids: These are further divided into three classes.

a) Containing -6+3- b) Containing -6+4- c) Containing -6+5-

membered rings membered rings. membered rings.

13
B) Sesquiterpenoids:

◦ i) Acyclic sesquiterpenoids ii) Monocyclic sesquiterpenoids iii) Bicyclic sesquiterpenoids.

14
C) Diterpenoids:
i) Acyclic diterpenoids

ii) Mono cyclic diterpenoids:

15
Isolation of mono and sesquiterpenoids
◦ Both mono and sesquiterpenoids have common source i.e essential oils. Their isolation is
carried out in two steps:

i) Isolation of essential oils from plant parts: The plants having essential oils generally have the
highest concentration at some particular time. Therefore better yield of essential oil plant
material have to be collected at this particular time. e.g. From jasmine at sunset. There are
four methods of extractions of oils.

a) Expression method

b) Steam distillation method

c) Extraction by means of volatile solvents

d) Adsorption in purified fats

16
Isolation of mono and sesquiterpenoids
◦ Steam distillation is most widely used method. In this method macerated plant material is
steam distilled to get essential oils into the distillate form these are extracted by using pure
organic volatile solvents. If compound decomposes during steam distillation, it may be
extracted with petrol at 50 ˚C. After extraction solvent is removed under reduced pressure.

ii) Separation of Terpenoids from essential oil: A number of terpenoids are present in essential
oil obtained from the extraction. Definite physical and chemical methods can be used for
the separation of terpenoids. They are separated by fractional distillation. The terpenoid
hydrocarbons distill over first followed by the oxygenated derivatives. More recently different
chromatographic techniques have been used both for isolation and separation of
terpenoids.
17
General properties of Terpenoids

1. Most of the terpenoids are colourless, fragrant liquids which are lighter than water and
volatile with steam. A few of them are solids e.g. camphor. All are soluble in organic solvent
and usually insoluble in water. Most of them are optically active.

2. They are open chain or cyclic unsaturated compounds having one or more double bonds.
Consequently they undergo addition reaction with hydrogen, halogen, acids, etc. A number
of addition products have antiseptic properties.

3. They undergo polymerization and dehydrogenation

4. They are easily oxidized nearly by all the oxidizing agents. On thermal decomposition, most
of the terpenoids yields isoprene as one of the product. 18
General Methods of structure elucidation
Terpenoids

i) Molecular formula: molecular formula is determined by usual quantitative analysis and mol.wt
determination methods and by means of mass spectrometry. If terpenoid is optically active, its specific
rotation can be measured.

ii) Nature of oxygen atom present: If oxygen is present in terpenoids its functional nature is
generally as alcohol aledhyde, ketone or carboxylic groups.
a) Presence of oxygen atom present: presence of –OH group can be determined by the formation of
acetates with acetic anhydride and benzoyate with 3,5-dinitirobenzoyl chloride.

b) Presence of >C=O group: Terpenoids containing carbonyl function form crystalline addition products
like oxime, phenyl hydrazone and bisulphite etc.

19
General Methods of structure elucidation
iii) Unsaturation:
The presence of olefinic double bond is confirmed by means of bromine, and number of double bond
determination by analysis of the bromide or by quantitative hydrogenation or by titration with
monoperpthalic acid. Presence of double bond also confirmed by means of catalytic hydrogenation
or addition of halogen acids. Number of moles of HX absorbed by one molecule is equal to number of
double bonds present.

Addition of nitrosyl chloride(NOCl) (Tilden’s reagent) and epoxide formation with peracid also gives
idea about double bonds present in terpenoid molecule.

20
General Methods of structure elucidation
iv) Dehydrogenation:
◦ On dehydrogenation with Sulphur or selenium, terpenoids converted to aromatic compounds.
Examination of these products the skelton structure and position of side chain in the original
terpenoids can be determined. For example α-terpineol on Se-dehydrogenation yields para-cymene.

v) Oxidative degradation:
o Oxidative degradation has been the parallel tool for elucidating the structure of terpenoids. Reagents
for degradative oxidation are ozone, acid, neutral or alkaline potassium permanganate, chromic
acid, sodium hypobromide, osmium tetroxide, nitric acid, lead tetra acetate and peroxy acids. Since
oxidizing agents are selective, depending on a particular group to be oxidized, the oxidizing agent is
chosen with the help of structure of degradation products. 21
General Methods of structure elucidation
vi) Relation between general formula of compound and type of compounds:
For example limonene (mol. formula. C10H16) absorbs 2 moles of hydrogen to give tetrahydro limonene
(mol. Formula C10H20) corresponding to the general formula. CnH2n. It means limonoene has
monocyclic structure.

limonene

vii) Spectroscopic studies:

UV Spectroscopy: In terpenes containing conjugated dienes or α,β-unsaturated ketones, UV
spectroscopy is very useful tool, IR Spectroscopy: IR spectroscopy is useful in detecting group such as
hydroxyl group (~3400cm-1) or an oxo group (saturated 1750-1700cm-1), NMR Spectroscopy, Mass
Spectroscopy, and X-ray analysis
22
Separation and isolation of terpenoids from volatile oil
◦ Chemical method:
1) Separation of terpenoid hydrocarbon: These are
separated by using Tilden’s reagent composed of
solution of Nitrosyl chloride (NOCl) in chloroform. The
terpenoid hydrocarbons on treatment with Tilden
reagent forms crystalline adduct having sharp m.p.,
which is separated from volatile oil followed by
hydrolysis or decomposed to get back the terpenoid
hydrocarbon.
2) Separation of terpenoid alcohol:
Terpenoid alcohols on reaction with Pthallic anhydride
forms di-ester, which precipitate out from volatile oil.
These di-esters on treatment with NaHCO3 in presence
KOH, yields back terpene alcohol and Pthallic acid
3) Separation of terpenoid aldehyde and ketone:
Terpenoid aldehydes and ketones forms crystalline
adduct on reaction with NaHSO3 and phenyl hydrazines
etc. These crystalline adducts can be hydrolyzed to get
back carbonyl compounds. 23
Myrcene
◦ Chemical formula: C10H16, b.p. 166-168°C. 𝜂 20D 1.4692
Myrcene is an acyclic monoterpene hydrocarbon occurring
in Verbena oil. is a colorless, liquid with a pleasant odor.

UV: λmax 225 nm.

IR: υmax , 1672, 1634, 1597, 997. 900, 893 cm-1.
1H NMR: δ 1.56, 1.63 (6H, C-7 methyls), 4.83-5.07 (m, 5H, H-1a, H-1b, H-

10a, H-10b and H-6), 6.19 (dd. 1H. H-2).

13 C NMR: δ 15.5 (C- 1), 139.0 (C-2), 145.9 (C-3), 30.8 (C-4), 26.1 (C-5),

124.4 (C-6), 131.0(C-7), 17.1 (C-8). 25.1 (C-9). 112.6 (C-10).

25
Structure elucidation
◦ The molecular formula of myrcene was found to be C10H16
1. On catalytic hydrogenation it gave a saturated hydrocarbon C10H22, indicating the
presence of three double bonds and hence myrcene must be acyclic.

2. Of the three double bonds two were conjugated was revealed by the UV spectrum of
myrcene. which showed maxima at 225 nm. This was supported by the optical exaltation
exhibited by myrcene in addition to formation of an adduct with maleic anhydride by
Diels-Alder reaction.

26
Structure elucidation
◦ Myrcene on ozonolysis afforded formaldehyde, acetone and a ketoaldehyde, C5H6O3 .
◦ The ketoaldehyde on oxidation with chromic acid gave succinic acid. Based on these data
structure as shown was assigned to myrcene.

◦ Myrcene was confirmed by hydrating with sulfuric acid to form the alcohol geraniol
followed by oxidation to citral.

27
Geraniol Methyl isovalerate

◦ Chemical formula: C10H18, b.p. 229-230 °C. 𝜂20D 1.4777

◦ Geraniol occurs in citronella, rose, lemon grass and lavender oils. It
is present in either free state or as esters. Its various esters such as
acetate, formate, butyrate and isovalerate are extensively used in
perfumery.

IR: υmax , 3400 (OH), 1695, 1105, 1090, 1000, 830 cm-1.
1H NMR: δ 1.62, 1.68 (6H, C-7 methyls), 4.15 (2H, α allylic CH OH), 5.12
2
(1H, m, H-6), 5.45 (t, 1H, H-2).

13 CNMR: δ 58.7 (C-1), 124.5 (C-2), 137.2 (C-3), 39.7 (C-4), 26.6 (C-5).
124.9 (C-6), 131.2 (C-7), 25.5 (C-8), 17.4 (C-9), 16.0 (C-10).
. 28
Structure elucidation
◦ Its molecular formula was established as C10H18O.
◦ Catalytic hydrogenation yielded a tetrahydro derivative C10H22O indicating the presence of
two double bonds.
◦ This was further supported by the formation of a tetrabromide when treated with bromine

◦ On oxidation geraniol afforded citral. which on reduction gave two alcohols.

29
Structure elucidation
◦ Geraniol and nerol are geometrical
isomers.
◦ Both geraniol and nerol gave the same
tetrahydro derivative on catalytic
hydrogenation.
◦ Both of them underwent cyclisation to
give terpeneol by the action of sulphuric
acid and the rate of cyclisation in the
case of nerol was 9 times faster
compared to that of geraniol.
◦ Based on this Δ2 -double bond in nerol
was assigned as cis while the same
double bond in geraniol as trans.

30
Citral
◦ Chemical formula: C10H16, b.p. 77 °C. 𝜂20D 1.4898
◦ Citral is one of the major constituents of lemon grass oil.

Mixture of at least 4
geometrical isomers of
di-olefinic aldehyde

Trans-citral cis-citral
UV: λmax 236 nm.
IR: υmax , 1665, 1625. 1603, 1398. 1190, 1117 cm-1.
1H NMR: δ 1.65 (6H, d, C-7 methyls), 2.15 (3H, s, C-3 Me), 5.0 (1H, t, H-6),

5.8 (1H, d, H-2), 9.84 (1H, d, H-1).

13 C NMR: δ 190 (C-1). 127-5 (C-2), 162.1 (C-3).405 (C-4), 265 (C-5),

123.5 (C-6). 132.3 (C-7). 25.3 (C-8), 17.4 (C-9), 17.0 (C-10).
MS: m/z 69 (100), 41, 84. 94, 109, 67. 83. 81. 31
Structure elucidation
◦ Formation of an oxime of citral indicated the presence of an oxo group in citral.
CHO CH N OH

+ NH2OH

Citral (a)
Oxim
Geranial (trans)

◦ Citral when heated with potassium hydrogen sulphate afforded the known aromatic
hydrocarbon, p-cymene, which fixed the position of methyl and isopropyl groups in citral.

32
Structure elucidation O OH

◦ Citral formed both mono- and di- bisulphites by H SO3 Na

the addition of sodium bisulfite to reveal the NaHSO3

presence of a conjugated aldehyde group. Its
UV spectrum displayed a band at 238 nm to
confirm this.

◦ Citral on reduction with sodium-amalgam citral

gave an alcohol, geraniol, C10H18O.

33
Structure elucidation
◦ Citral on oxidation with alkaline permanganate, yielded acetone, oxalic and levulenic acid.

CHO
i) KMnO4
ii) CrO3
+ +

Citral (a)
Geranial (trans)

◦ Citral oxidation with silver oxide afforded an acid

geranic acid, C10H16O2 containing the same
number of carbon atoms suggesting that citral
had an aldehyde group.

34
Structure elucidation
Based on the above data and coupled with the biogenetic considerations that citral is
formed by the joining of two isoprene units in the head to tail fashion, structure of citral was
assigned tentatively.

This structure was further supported by the degradation of citral on treatment with aqueous
potassium carbonate when 6-methyl-hept-5-en-2-one and acetaldehyde were obtained.
The structure of citral was finally confirmed by its synthesis.

35
(-)-Menthol
◦ Chemical formula: C10H20O, m.p. 34 °C, b.p. 213 °C, [α]D -50°, 𝜂20D
1.4661.
◦ Menthol is the major constituent of Mentha piperita and has been
known in India, China and Japan since ancient times. It is mainly
used as flavouring agent and has a cooling effect. Medicinally it
exhibits antiseptic and anaesthetic properties. It is the ingredient in
cold balms.
IR: υmax , 3333, 1048, 1028, 994, 977, 920, 876, 845 cm-1.
1H NMR: δ 0.82 (3H, d, C-1 Me), 0.90, 0.93 (3H each, d, C-7 methyls), 3.42 (1H,m,

H-3).
13 C NMR: δ 31.7 (C-1). 45.2 (C-2), 71.5 (C-3), 50.2 (C-4), 23.3 (C-5), 34.6(C-6),

25.8 (C-7), 16.1

MS: m/z 71 (100), 81, 95, 41, 55, 82, 43, 123.

36
Structure elucidation

Molecular formula of menthol was determined as

OH
C10H20O. On treatment with phosphorus PCl5
pentachloride and phosphorus pentoxide Menthol
menthol gave a chloride C10H19Cl and a Cl
P2O5
hydrocarbon C10H18 respectively, inferring that it is
an alcohol. Menthyl chloride

37
Structure elucidation

• Menthol was oxidized by chromic acid to a

ketone, Menthone to prove that menthol
contained a secondary hydroxyl group.

• Menthol was converted to p-cymene identified

as 1-methyl-4-isopropylbenzene, which was
also obtained by the dehydrogenation of
pulegone whose structure was established as p-
menth-4-(8)-en-3-one by chemical methods
and confirmed by its synthesis.

• Therefore menthol must possess the same

skeleton as pulegone.

• Pulegone on reduction yielded menthone,

which on further reduction gave menthol.
• correlation of pulegone with menthol proved the
structure of menthol. 38
Stereochemistry

• Menthol has three asymmetric

centers namely C1, C3 and C4.
In view of the three chiral
centers, eight optically active
forms are possible and all the
eight enantiomers are known.
Four isomers are shown in
Figure.
• Stereochemistry at C1 and C4 was established
by correlation to
D-(+)- methylsuccinic acid and
D-(+)-isopropylsuccinic acid
respectively by the sequence of reactions
shown in Figure.
39
Limonene 7

Occurrence:
◦ Limonene is one of the most widely distributed terpene, occurring in many 1
volatile oils especially in citrus oils.
◦ The d- form (+) is present orange (90%), lime, grapefruit, bitter orange,
mandarin, neroli, dill fennel.
◦ The 1 form (-) is less common, accur in peppermint, spearmint. The recemic
form dl (± ) is known as dipentine and occurs in volatile oils of lemon grass, 8
nutmeg, neroli, fennel etc. 9 10
Isolation:
o Limonene is isolated from the volatile oil either by careful fractional distillation, b.p 176°C
without decomposition, or via certain derivative (adducts) e.g., tetrabromide m.p 104°-
105°C. and the hydrocarbon may be regenerated by debromination with zinc and acetic
acid. 40
Limonene
◦ Limonene is identified by the preparation of a crystalline nitrosochloride m.p 103°-104°C., by
the reaction with nitrosyl chloride gas and the crystalline tetra bromide, m.p 104°-105°C.
◦ Autoxidation of limonene to corveol and carvone under the influence of air and moisture, is
most probably one of the principal factors in the spoilage of poorly stored oils that contain
high percentage of limonene e.g. citrus oils. This is particularly noticeable in old orange oils by
showing peculiar caraway odor.
7

1
H2O
O2
8
9 10

Uses :
• Limonene is widely employed for scenting cosmetics, soaps as well as for flavoring pharmaceuticals. 41
Bicyclic monoterpenoids
Pinene
-Pinene, b.p. 156°C. This is the most important
member of the pinane class. It occurs in both the (+)-
and (-)-forms in all turpentine oils.

β- Pinene is a colorless liquid that boils at1630C

Double bond Br
Br
2,3-
Dibromopinane

OH

Trans 1,8 -Terpin

α-Pinene
OH

CH2Br
Br
+ Br2

β-Pinene
1,2-Dibromopinane
Oxidation
Since pinene easily oxidized by ozone, the air in the pine forest and the
surrounding area is very good for human health, especially the tuberculosis.

Pinene has special importance for the preparation of aliphatic compound

or compounds or single-ring camphan

One ring system α-terpineol

+H+

α-Pinene
Myrcene
Polyterpenoids
◦ Polymeric isoprenoid hydrocarbons ; Rubber is occurs as a colloidal suspension called latex
in a number of plants mainly in a rubber tree (Hevea brasiliensis).
◦ Rubber is a polyene, and exhibits all the expected reactions of the C=C function. Bromine,
hydrogen chloride and hydrogen all add with one molar equivalent per isoprene unit.
◦ Ozonolysis of rubber generates a mixture of levulinic acid ( CH3COCH2CH2CO2H ) and the
corresponding aldehyde.
◦ Pyrolysis of rubber produces the diene isoprene along with other products.

Levulinic acid

46
Polyterpenoids
◦ The double bonds in rubber all have a Z-configuration, which causes this macromolecule to
adopt a coiled conformation and high molecular weight (about one million).
◦ Physical properties of rubber: crude latex rubber is a soft, sticky, elastic substance.

◦ Chemical modification of this material for commercial applications: Gutta-percha (structure

above) is a naturally occurring E-isomer of rubber.
◦ Here the hydrocarbon chains adopt a uniform zig-zag conformation, more rigid and tough
substance. Uses: surgical devices and during root canal therapy and Electrical insulation.
◦ gutta-percha is the trans-form. Gutta-percha is hard and has a very low elasticity.

47
Polyterpenoids
Rubber:
◦ Rubber is obtained from latex, which is an emulsion
of rubber particles in water that is obtained from
the inner bark of many types of trees which grow in
the tropics and sub-tropics.
◦ When the bark of the rubber trees is cut, latex
slowly exudes from the cut.
◦ Addition of the acetic acid coagulates the
rubber, which is then separated from the liquor
and either pressed into blocks or rolled into sheets,
and finally dried in a current of warm air, or
smoked.

After coagulation, the cake of raw

rubber must be rolled to remove the
water and washed to remove the acid 48
Rubber
◦ Crude latex rubber contains, in addition to the actual rubber hydrocarbons
(90-5 percent), proteins, sugars fatty acids and resins, the amounts of these
substances depending on the source.
◦ Crude rubber is soft and sticky, becoming more so as the temperature rises.
◦ It has a low tensile strength and its elasticity is exhibited only over a narrow
range of temperature.
◦ When treated with solvents such as benzene, ether, light petrol, a large part
of the crude rubber dissolves; the rest swells but does not dissolve. This
insoluble fraction apparently contains almost all of the protein impurity.
◦ On the other hand, rubber is insoluble in acetone, methanol, etc.
◦ When un-stretched, rubber is amorphous; stretching or prolonged cooling
causes rubber to crystallize.
49
Structure of rubber

◦ The destructive distillation of rubber gives isoprene as one of the main

products; this led to the suggestion that rubber is a polymer of isoprene,
◦ and therefore to the molecular formula (C5H8)n. This molecular formula has
been confirmed by the analysis of pure rubber.
◦ Crude rubber may be purified by fractional precipitation from benzene
solution by the addition of acetone.
◦ This fractional precipitation, however, produces molecules of different sizes,
as shown by the determination of the molecular weights of the various
fractions by osmotic pressure, viscosity and ultracentrifuge measurements;
molecular weights of the order of 300 000 have been obtained.

50
Structure of rubber

◦ The halogens and the halogen acids readily add on the rubber, e.g.,
bromine gives an addition product of formula (C5H8Br2)n, and the hydrogen
chloride the addition product (C5H9Cl)n.
◦ Pummerer in 1922 showed that Pure rubber has been hydrogenated to the
fully saturated hydrocarbon (C5H10)n – this is known as hydrorubber – by
heating with hydrogen in the presence of platinum as catalyst.
◦ Rubber also forms an ozonide of formula.

◦ All these addition reactions clearly indicate that rubber is an unsaturated

compound, and the formulae of the addition products show that there is
one double bond for each isoprene unit present. 51
Ozonolysis
◦ Ozonolysis of rubber produces laevulaldehyde and its peroxide, laevulic
acid and small amounts of carbon dioxide, formic acid and succinic acid
◦ laevulic derivatives comprised about 90 percent of the products formed by
the ozonolysis.

O3 +
OHC O
O
rubber

+ +
OHC O OHC

52
Ozonolysis
◦ This observation led to the suggestion that rubber is composed of isoprene
units joined head to tail. Thus, if rubber has the following structure, the
formation of the products of ozonolysis can be explained as in the previous
scheme.
◦ Some of the laevulaldehyde is further oxidized to laevulic and succinic acids.
O

O CO2H
Laevulic acid
CHO

CO2 + HO2C
CO2H
succinic acids 53
Thank You
54