ORGANIC CHEMISTRY

MAXIMINO P. VILLAHERMOSA, JR.

FAR EASTERN UNIVERSITY
APRIL 2009

THE BEGINNINGS OF ORGANIC

CHEM

Ever since the discovery of

fire, mankind was inevitably
bound to divide substances
into two classes: those that
burned and those that did not.
At the end of the 18th
century, two broad classes of
materials were recognized.
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Minerals or substances of mineral origin

in rocks and oceans were usually found
to be stable against strong heating
except when they underwent specific
chemical transformations. In contrast,
substances derived from living or onceliving things would char or burn when
heated. Water may be boiled or
condensed back to water, salt could be
melted and recrystallized into the original cpd.

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Olive oil or sugar, however, when

heated even under conditions that
prevented burning, turned to
fume, smoke and char. What was
left was not olive oil or sugar, nor
could olive oil or sugar be
reformed out of its remains.

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LIVING THINGS

NON-LIVING THINGS

In

1807, J.J. Berzelius, a Scandinavian, who,

as a medical student, was attracted to
Chemistry above all other subjects in his
curriculum, suggested that substances like
olive oil or sugar, the characteristic product
of organisms, should be called organic.
Substances like water or salt, characteristic
of non-living environment, were thus
inorganic.
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Vital Force Theory

Berzelius argued that organic
substances could be formed
only under the influence of a
vital force operating within
living systems. Once formed
and present in dead matter,
organic substances can be
changed into inorganic ones,
but never had the reverse
sequence been observed.

It was for this reason that

chemists argued that inorganic
substances might be found
anywhere, as water might be
found in both ocean and the
blood.

Organic substance, requiring the

vital force, would be found only in
connection with life.
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This view was proven wrong in

1828 by the work of Friedrich
Wohler, a German chemist, who
had been a pupil of Berzelius.
Wohler gently heated an inorganic
salt-like material, NH4CNO, and
found the product to be urea, a
waste product eliminated in
considerable quantity in the urine
of many animals, including man.
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Wohler

repeated the experiment a number of

times and found that he could convert an
inorganic substance to an organic substance
at will. He told his teacher about this and
Berzelius was forced to agree that the line he
had drawn between organic and inorganic
substance was not as tight as he thought.

This

feat seemed to be the initial defeat of

the vitalism theory.
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The conversion of inorganic matter to

an organic compound was the first
evidence for what has since been
found to be universally true:

Matter at the atomic and molecular

level is the same whether manipulated
within a living organism or not.

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Synthesis of Organic
Compounds

In 1845, Adolph W.H. Kolbe, a

student of Wohler, succeeded in
synthesizing CH3COOH from its
constituent elements: C,H, and
O. If Wohlers observations
about urea did not quite settle
the matter of vital force, Kolbes
synthesis of CH3COOH did.
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 During

the 1850s, the French chemist Pierre

E.M. Berthelot went about the systematic
prepn of organic cpds including well known
subst as CH3OH, EtOH, CH4 , C6H6, and C2H2.

By

the mid-19th century the division of

compounds into organic & inorganic on the
basis of the activity of the living organism
had become obsolete. More and more, the
difference between organic and inorganic
substance was found to be in chemical
structures.
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Most

organic substances were made up of

from 2 to 8 elements.

It

became also notable that all organic subst

contained one or more Carbon atoms in their
molecules, & almost all contained H atoms as
well.

In

1881, the German chemist Fried-rich A.

Kekule, redefined organic chem as the
chemistry of C cpds. CO2, CO32- , HCO3- & CNare exceptions.
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Since the mid-19th century, about 6

M organic cpds have been identified,
many synthesized in the Lab from
inorg cpds.

Virtually all plastics synthetic and

natural fibers, dyes + drugs,
insecticides + herbicides, and
ingredients in perfumes, are organic.
Vitamins, hormones and foods are
mostly, if not entirely involved in the
chemistry of living things.

Organic Chemistry
Chemistry of the compounds of
C
Everywhere around us:
foods, flavors, and
fragrances
medicines, toiletries and
cosmetics
plastics, films, fibers and
resins

The unique ability of C to form bonds

with another C atom and with H
atoms is the realm of organic chem.

Probably 2 of the branches of org

chem that has the largest impact in
modern-day living are synthetic
organic chem and natural product
chem. In some instances, both fields
might be supportive of each other.

Synthetic organic chem, as the name

implies, deals with the synthesis of more
complex molecules from simpler ones.

Examples of the results of this

fascinating branch of chem are synthetic
polymers, medicines, insecticides +
other Carbon-based materials which
make modern-day life more convenient.

Traditionally, the study of natural products

chem mainly deals with 20 metabolites.
As opposed to 10 metabolites, which
have the function of building or breaking
down cpds of the organisms, 20
metabolites are produced by the
organism for some specific roles such as
adaptation, defense, survival etc.
Traditional drugs + medicines, perfumes,
plant pigments, natural insecticides,
toxins + other cpds are common ex. of
nat. cpds which are extracted from
organisms.

Involve the chemistry of C and only a

few of other elementschiefly, H, O,
and N; may also contain S, P, and a
halogen (F, Cl, Br, or I)

C not even among the ten most

abundant elements; approx. 75% of the
earths crust is O and Si, components
of silicate minerals, clays and sand; C
only one of the remaining 0.9% of the
earths crust
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Why Study Organic Chem?

1. Historicalvitalism theory
2. Sheer number of organic cpds
10 million and still counting
1.7 million only (inorganic)
3. Biochemicals are organic cpds
4. Organic cpds differ fr inorg cpds
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COMPARISON OF
PROPERTIES
ORGANIC COMPOUNDS
1.
2.
3.
4.

5.
6.
7.

Covalent bonding
Low melting pt -S,L,G
Insoluble in H2O
Soluble in organic
solvents
Non-electrolyte
Almost all burn
Slow reaction

INORGANIC CPDS
1.
2.
3.
4.

5.
6.
7.

Ionic bonding
High melting pt solids
Soluble in water
Insoluble in organic
solvents
Electrolytes
Very few burn
Fast reaction
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Where Do We Obtain Org. Cpds?

Isolation from Nature: Living

things are chemical factories;
organic cpds are extracted,
isolated, and purified from
biological sources
Examples: Vit. E, the penicillins,
table sugar, insulin, quinine,
anti-cancer drug paclitaxel; also
natural gas, coal, petroleum
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jun2009

Plant sources: starch, sugar,

fibers, cellulose, oils, especially
waxy varieties of plants are known
to be sources of high mw alkanes
Quinine from bark of cinchona tree
Malic acid from apples
Alkenes /cycloalkenes like rubber
turpentene, essential oils and
colored plant pigments
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Animal Sources: fats, proteins

and amino acids; cholesterol
from gallstones; urea from liver
Natural gas and petroleum
products from the underground
decay of animals, plants and
marine residues
o Nat. gasCH , C H , C H , C H
4
2 6
3 8
4 10
o Petroleumfractional distillation
gasoline, kerosene, lube oils,
tar,

paraffin, petroleum ether

Coalone of the major sources of
aromatic hydrocarbon
coal destructive distn coal tar
C6H6, naphthalene, phenol fractional
distillation

Fermentationpxs of
enzymatically
controlled anaerobic breakdown
of energy-rich compounds

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Synthesis in the Laboratory: Few

natural organic cpds, no matter how
complicated, that chemists cannot
synthesize in the Lab
Cpds, natural or synthetic have
identical physical & chemical
properties
Chemists have also designed &
synthesized cpds not found in nature

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Majority of the 10 M
organic cpds are purely
synthetic and do not
exist in living
organisms.
Examples: Modern
drugsValium, albuterol, Prozac, Zantac,
Viagra, ibuprofen,
aspirinnot found in
nature

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GENERAL CLASSIFICATION OF
ORGANIC COMPOUNDS
1. Hydrocarbonscpds contg C and H
o HC in open chain (aliphatic)
a. Saturated hydrocarbons
alkanessingle bond CnH2n+2
b. Unsaturated hydrocarbons
alkenesdouble bond CnH2n
alkynestriple bond CnH2n-2
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HC in closed chain or ring

a. Aromatic Hydrocarbon
benzene
naphthalene
C6H6
C10H8
b. Alicyclic Hydrocarbon
cycloalkane (single bond closed)
cycloalkene
cycloalkyne
c. Heterocyclic cpds
niacin (nicotinamide)
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C=O
NH2

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2. C,H,Xalkyl halide
Type formula: C H X or RX
CCl methyl chloride
CCCBr -bromopropane
3. C,H,O

Alcoholgeneral formula ROH

COH or CH3-OH methyl alcohol
CCOH or C2H5OH ethyl alcohol
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Ethergeneral formula: ROR

CH3OCH3
or
COC
dimethyl ether
O

Aldehydegeneral formula: RC
HCHO or
C=O formaldehyde
H
or methanal
CH3CHO or CC=O
acetaldehyde or ethanal
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Ketonegeneral formula: RC=O

CH3C=O or
CC=O
R
CH3 2-propanone
C or acetone

Carboxylic acidgeneral formula:

RC=O
HC=O methanoic
acid
OH
OH or formic
acid CH3COOH
or
CC=O
ethanoic or acetic acid
OH
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Estersgeneral formula: RC=O

CH3C=O
ethyl acetate
OR
OCH2CH3 or ethyl ethanoate

Acid anhydridegeneral formula:

CH3C=O
RC=O

CH 3C=O O

RC=O

ethanoic anhydride or acetic anhydride

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4. C,H,O,N
a. Nitro compounds:
RNO 2
CNO2
or
CH3NO2
methyl nitrite
b. Amides:
RC=O
NH2
CC=O
or
CH 3C=O
NH2
NH 2
ethanamide
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5. C,H,N
a. Cyanidesgeneral formula: RCN
CH3CN
or CCN
methyl cyanide
b. Aminesgeneral formula: RNH 2
CH3NH2
or CNH2
methyl amine
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2009