ORGANIC COMPOUND

SPECIFIC LEARNING OBJECTIVE

At the end of the session the student should be able to
Explain:
- Hydrocarbons, Alcohols, Phenols, Halogen
compounds, Eters, Aldehydes, Ketone, Acids, Acid
derivatives, Diazonium compounds (salts), Amines,
Amino acids, Aromatic nitro compound, Isomerism,
and bio organic compound
- Organic compound reaction mechanism

Organic Compound 1
 Introduction

All organic chemistry is based upon

unique properties of the carbon atom.
Carbon, C, hybridization to 3 sp3
orbitals, carbon can now form 4 bonds,
may be single, or in combination of
double (sp2) or triple bonds (sp).
Carbon forms very strong bonds with
many non-metal atoms, H, O, Cl, N.

Organic Compound 2
ORGANIC CHEMISTRY

1 ORGANIC COMPOUND

BIO ORGANIC
2
COMPOUND

Organic Compound 3
 ORGANIC CHEMISTRY

CLASSIFICATION

THE TOPICS

Organic Compound 4
 1 ORGANIC COMPOUND

CLASSIFICATION THE TOPICS

HYDROCARBON STRUCTURE

ALCOHOLS, PHENOLS, REACTION

THIOLS & ETHERS
PHYSICAL
ALDEHYDES & KETONS PROPERTIES

AMINES & AMIDES FUNCTIONS

Organic Compound 5
 HYDROCARBON - R-H

STRUCTURE

A B

Aliphatic Aromatic
SATURATED

UNSATURATED

Organic Compound 6
 Alkanes  CH3 - CH3

Aliphatic Alkenes  CH2 = CH2

Alkynes  CH = CH

Aromatic
cyclohexane cyclopropane

Organic Compound 7
 Alkanes  CH3 - CH3 or R-H
(paraffins)

CH3CH2CH3  propane
cyclohexane

Reaction/Properties :
1.Reaction with oxygen:Occurs during
combustion in an engine or furnace when
alkane is used as a fuel.
CH4 + 2O2  CO2 + 2H2O +213 kcal/mol
continued
Organic Compound 8
Continued: Alkanes

Reaction/Properties :
2.Reaction with Cl2:Occurs when a mixture of
the two is irradiated with ultraviolet light.
uv
CH4 + Cl2  CH3Cl + HCl
uv
CH3Cl + Cl2  CH2Cl2 + HCl
uv
CH2Cl2 + Cl2  CH3Cl + HCl
CHCl3 + Cl2  CCl4 + HCl
uv

3. Properties of alkanes: alkanes show

increases in both boiling point and melting
point as molecular weight increases

Organic Compound 9
 FUNCTION

Alkanes  CH3 - CH3 or R-H (paraffins)

 Alifatic : as solvent and the properties
are toxins to human body
 For example:
 n-hexane
 dichlorometane

 continued:
Organic Compound 10
 FUNCTION

 Polyhalogenated Hydrocarbons :

Toxins Drugs
 Toxins : insecticides such as DDT,
Chlordane, kepone and lindane do not
break down rapidly in the environment
 Drugs : Polyhalogenated Hydrocar-
bons are very useful in medicine :
chloroethane, chloromethane trichlo-
romethane (chloroform).
continued:
Organic Compound 11
 Chloroethane  CH3CH2–Cl
 Chloromethane  CH3–Cl
 trichloromethane  CHCl3 (chloroform)
 chloroethane, chloromethane are local
anaesthetics.
 trichloromethane (chloroform) was used
as both a general and a local anesthetic.
When administered through inhalation, it
rapidly causes loss of consciousness.
However, the effects of this powerful
anesthetics are of short duration.
it was shown to be carcinogenic
Organic Compound 12
 Halothane or 1-Bromo-1-
chloroethane
H
H3C C Br

Cl

 Is a general anesthetic (last time)

that is administered by inhalation. It
is considered to be a very safe
anesthetic and is widely used.
Organic Compound 13
 Isomerism in alkanes

HH H H
H-C-C-O-H ; H-C-O-C-H
HH H H

ethyl alcohol dimethyl ether

Organic Compound 14
 Cis-Trans Isomerism in Cycloalkanes

Cl Cl Cl

Cl

 Cis Trans

Organic Compound 15
From top side From one side –
horizontal
Organic Compound 16
The structure of the molecule make the
specific properties

Organic Compound 17
 shorter 0,134 nm

0,154 nm

109,5° single bond

Organic Compound 18
Alkenes  CH2 = CH2 or R- CH2 = CH2
(olefins)

CH2 = CH2
ethylene

cyclohexene

Organic Compound 19
Reaction/Properties :
1. The addition reaction:
A. Hydrogenation : addition of H2 to
an alkene
B. Halogenation : addition of Cl2 to
an alkene
C. Hydration : addition of H2O to
an alkene
D. Hydrohalogenation : addition of
HX to an alkene

Organic Compound 20
 A generalized addition reaction is :

R R R
C A R C A
+
C B R C B
R R R

 The product of this reaction is either

an alkane or substituted alkane

Organic Compound 21
 Aromatic Hydrocarbons

 Structure and Properties

H H
H H H H

H H H H
H H
 Benzene

Organic Compound 22
Reaction/Properties of benzene:
1. The typical reactions of benzene are
substitution reactions, in which a
hydrogen atom is replaced by
another atom group of atoms
A. Benzene can react with Cl2 or Br2
is called halogenation
B. Benzene can react with SO3
is called sulfonation
C. Benzene can react with nitric acid
is called nitration
Organic Compound 23
A. Halogenation with Cl2 or Br2
Br
FeBr3
+ Br2 + HBr

Bromo benzene

FeCl3.
Cl2 + HCl
B. sulfonation with SO3 (H2SO4 conc) 
Benzene sulfonic acid NO 2

C. Nitration with HNO3 (H2SO4 conc) 

Nitrobenzene
Organic Compound 24
When two group are present on the ring, three
possible orientations exist

 Two groups G
G G

G
G

Two groups Two groups Two groups

1,2 or ortho 1,3 or meta 1,4 or para
(o) (m) (p)
Organic Compound 25
 FUNCTION
 For example
H H H H H H H H H H H H H O
H C C C C C C C C C C C C C C O H
H H H H H H C C H H H H H H H
H H  Palmitoleic acid

H3C CH3
OH
 Vitamin A
CH3
O
CH 3
 Vitamin K
CH 3

O CH 3 CH 3 CH 3 CH 3
Organic Compound 26
 FUNCTION

 For example
H Cl

Cl C C Cl
Cl

Cl
 DDT: Dichlorodiphenyltrichloroethane

Organic Compound 27
 1 ORGANIC COMPOUND

CLASSIFICATION THE TOPICS

HYDROCARBON STRUCTURE

ALCOHOLS, PHENOLS, REACTION

THIOLS & ETHERS
PHYSICAL
ALDEHYDES & KETONS PROPERTIES

AMINES & AMIDES FUNCTIONS

Organic Compound 28
ALCOHOLS, PHENOLS, THIOLS & ETHERS

STRUCTURE

A B

Aliphatic Aromatic
SATURATED

UNSATURATED

Organic Compound 29
 General Formula
O
ALCOHOLS R H

Alcohol

O
PHENOLS Ar H

Phenol

R SH
THIOLS Thiol
(R = R or Ar)

O
R R
ETHERS Ethers
(R and R1= R or Ar)
Organic Compound 30
ALCOHOLS : R – OH
O
R H

Alcohol
1. Primary (1st), R–CH2OH

CH3CH2CH2OH
1-propanol
(n-propyl alcohol)
31
2. Secondary (2nd), R2CH–OH
CH3 – CH – CH3
OH
2-propanol
(isopropyl alcohol)

3. Tertiary (3rd) R3C–OH

(CH3)3 COH
tert-butyl alcohol

32
 Properties of ALCOHOLS

 The R–O–H portion of O

an alcohol is similar to the R H
structure of water.
Alcohol
 The structure of the R–O–H is very
similar to the H–O–H (water)
 The hydroxyl groups of alcahol
molecules themselves, are very polar
because the oxygen and hydrogen
atoms have significantly different
electronegativies.
Organic Compound 33
continuation

 Because the two atoms involved in this polar

bond are oxygen and hydrogen, hydrogen bonds
can form between alcohol molecules.
 As a result of this intermolecular hydrogen
bonding, alcohols boil st much higher
temperatures than hydrocarbons of similar
molecular weight. These higher boiling points are
caused by the large amount of heat needed to
break the hydrogen bonds that attract the alcohol
molecules to one another.
 For example:
CH3CH2CH2CH3 CH3CH2CH2CH2OH
Butane (M.W. = 58) 1-Propanol (MW= 60)
b.p. = m – 0.5 °C b.p. = 97.2°C
Organic Compound 34
continuation

 Alcohol with fewer than four or five

carbon atoms are very soluble in
water, and those with five to eight
carbons are moderately soluble in
water.
 This is due to the ability of the alcohol
to form intermolecular hydrogen
bonds with water molecules.
 As the carbon chain length of an
alcohol increases, the influence of the
nonpolar hydrocarbon part of the
molecule increases.
 Thus the hydroxyl group has a
smaller effect. As a result, large
alcohols are nearly insoluble in water.
Organic Compound 35
 Reaction of Alcohols

 Preparation of Alcohols:
1. Addition reaction of alkene:
R R R
C H H+ R C H
+
C OH R C OH
R R R
H+
Alkene Water Alcohol

2. They may also be prepared via the

reduction of aldehydes and ketones.
This reaction, summarized as
O
follows +
H
H
C
catalyst
R
O
C R
R R H
H
Aldehyde or Hydrogen Alcohol
ketone

Organic Compound 36
continuation

1. Dehydration (lose water) of Alcohol

when heated with concentrated
sulfuric acid(H2SO4) or phosphoric
acid (H3PO4).
Dehydration is simply the reverse
process: the conversion of an
alcohol back to an alkene.
H H
+
H , heat
R C C H R CH CH2 + H OH

H OH
Alcohol Alkene Water

Organic Compound 37
 Reaction

2. Oxydation reaction : Alcohol may be

oxidized with a variety of oxidizing agents
to aldehydes, ketones, and carboxylic
acids
a. oxidation of a primary alcohol :
OH O
[O] C
R C H
H R H

An Aldehyde
10 Alcohol
i.e. oxidation of methanol :
OH O
[O]
H C H C
H H H

Methanol Methanal
(methyl alcohol) (formaldehyde)
An Alcohol An Aldehyde
Organic Compound 38
 Reaction
2. Oxydation reaction : Alcohol may be
oxidized with a variety of oxidizing agents
to aldehydes, ketones, and carboxylic
acids
a. oxidation of a secondary alcohol :
OH O
[O]
R C R C
H R R

A Ketone
2nd Alcohol

b. oxidation of a secondary alcohol :

OH
R
[O]
C R No reaction
R

rd
3 Alcohol

Organic Compound 39
The function of Alcohol

For health :
 Antiseptic
 Ethanol 70%

For industrial :
 Beverage
 Solvent

continued
Organic Compound 40
 PHENOLS : Ar – OH
Phenol are compounds in which
the hydroxyl group is attached
to a benzene ring.

Structure of the Phenol

O
Ar H

Phenol
Organic Compound 41
 OH
phenol

CH3
OH

o-cresol
(o-methylphenol)

continued

Organic Compound 42
 Reactions of Phenols

 Oxidation  Quinones:
O
OH

(KSO3)2NO
H2O

Phenol Benzoquinone (79%)

O OH

SnCl 2, H2O

Fremy's salt

O OH
Benzoquinone (79%) Hydroquinone

Organic Compound 43
 The function of Phenol

For health :
 Antiseptic
 Food preservative

For industrial :
 Raw material to manufacture the
explosive  picric acid (2,4,6-
trinitrophenol)
 Bleke resin and adhesive for
binding plywood.
Organic Compound
continued 44
The function of Phenol

O OH
OH
(H3C)3C C(CH3)3

SnCl 2, H2O

Fremy's salt

CH3
O OH
Hydroquinone Butylated hydroxy toluene.
Benzoquinone (79%)
BHT (food preservative)

continued
Organic Compound 45
The function of Phenol

OH
OH Cl Cl Cl
Cl
H2
C

OH Cl OH HO Cl
(CH2)5CH3 Hexachlorophene
o-Phenylphenol
Hexylresorcinol
(antiseptic)
(antiseptic)
(antiseptic)

Organic Compound 46
 General Formula
O
ALCOHOLS R H

Alcohol

O
PHENOLS Ar H

Phenol

R SH
THIOLS Thiol
(R = R or Ar)

O
R R
ETHERS Ethers
(R and R1= R or Ar)
Organic Compound 47
 THIOLS : R – SH

 Structures

R SH

Thiol
(R = R or Ar)

Organic Compound 48
 Properties of Thiols
 Thiols and many other sulfur compounds
have nauseating aromas
 Thiols are involved in protein structure
and conformation. It is the ability of two
thiol groups to easily undergo oxidation
to a disulfide bond (– S – S –) that is
responsible for this involvement.
 The thiol-disulfide interconversion is
extremely important in biochemistry,
where disulfide ”bridges” form the cross-
links between protein chains that help
stabilize the three-dimensional
conformations of proteins
Organic Compound 49
For example:
O
H
+ -
H3N C C O

H2C SH

Cysteine

Cysteine is an amino acid that

contains a sulfhydryl group.

continued
Organic Compound 50
 The primary structure of bovine insulin

This protein is composed of two polypeptide

chains (A and B) joined by disulfide bonds.
The A chain also contains an internal
disulfide bonds.
Organic Compound 51
 General Formula
O
ALCOHOLS R H

Alcohol

O
PHENOLS Ar H

Phenol

R SH
THIOLS Thiol
(R = R or Ar)

O
R R
ETHERS Ethers
(R and R1= R or Ar)
Organic Compound 52
 ETHERS

 General Formula : O
R R

Ethers
(R and R1= R or Ar)

 and thus they are structurally related to

alcohols (R–O–H). The C–O bonds are
polar, and thus ether molecules are polar.
However, ethers do not form hydrogen
bonds to one another because there is no
–OH group. Therefore they have much
lower boiling points than alcohols of
similar molecular weights but higher
boiling points than alkanes of similar
molecular weight.
Organic Compound 53
The boiling point of alkanes, ether and alcohol
CH3CH2CH2CH3
Butane (M.W. = 58)
b.p. = – 0.5 °C

CH3 – O – CH2CH3
Methoxyethane (M.W. = 60)
b.p. = 7.9 °C

CH3CH2CH2CH2OH
1-Propanol (MW= 60)
b.p. = 97.2°C
Organic Compound 54
 Properties of Ether

 Chemically ethers are moderately inert.

They do not react with reducing agents
or bases under normal conditions.
However, they are extremely volatile and
highly flammable, and hence must
always be treated with great care.

Organic Compound 55
 The function of Ether

 Diethyl ether : C2H5–O–C2H5

 Diethyl ether functions as an
anesthetic by interacting with the
central nervous system. It appears
that diethyl ether (and many other
general anesthetics) function by
accumulating in the lipid material of
the nerve cells, thereby interfering
with nerve impulse transmission.
This results in analgesia, a lessened
perception of pain.
Organic Compound 56
 1 ORGANIC COMPOUND

CLASSIFICATION THE TOPICS

HYDROCARBON STRUCTURE

ALCOHOLS, PHENOLS, REACTION

THIOLS & ETHERS
PHYSICAL
ALDEHYDES & KETONS PROPERTIES

AMINES & AMIDES FUNCTIONS

Organic Compound 57
 ALDEHYDES & KETONS

 The Structures of Aldehydes and ketones

O O O
C
C C
R H R R
The Carbonyl group
Aldehyde Ketone
R = H, R, or Ar R = R or Ar

Organic Compound 58
 Reaction Aldehydes and Keton

1. Addition reactions
O H OH

2 2
+ OR R' C OR
R' H
H
Aldehyde Alcohol Hemiacetal
H OH
O

3 3
+ OR R1 C OR
R' R'' 2
R
Keton Alcohol Hemiketal

Organic Compound 59
 Hemiacetal - hemiketal formation in sugar

 Hemiacetals and hemiketals are readily

formed in carbohydrates.
Monosaccharides contain several
hydroxyl groups and one carbonyl
group.
 Hemiacetals and hemiketals are very
reactive. If excess alcohol is present in
the reaction mixture, they will undergo a
substitution reaction in which the –OH
is exchanged for another –OR group.
The products of these reactions are
acetals and ketals.
continued
Organic Compound 60
 Acetal and Ketal formation

When hemiacetal or hemiketal of one

monosaccharide reacts with a hydroxyl
group of another monosaccharide, the
product is an acetal or a ketal. A sugar
molecule made up of two
Monosaccharides is called a disacharide.
The C–O–C bond between the two
Monosaccharides is called a glycosidic
bond.

Organic Compound 61
Glycosidic bond

Organic Compound 62
 Formula of Glycocidic bond

Continued
Organic Compound 63
 A New drug

 Combination Formula of Glycocidic

bond

Organic Compound 64
 ACIDS : R – CO2H

CO2H

CH3CO2H

benzoic acid acetic acid

Organic Compound 65
 ACIDS DERIVATIVE

1. di- and subtituted acids

CH2(CO2H)2
malonic acid

CH3CH(OH)CO2H
lactic acid

Organic compound 66
 2. Acid chlorides : R – COCl

CH3 – COCl COBr

acetyl chloride

benzoyl bromide

Organic Compound 67
 3. Esthers : RCO2R`
O

1 2
R C OR

H3CO2CH3 CH3 CO2CH3

methyl acetate

ethyl benzoate

CH2O2C – C ≡ C – CO2CH3
dimethyl acetylenedicarboxylate
68
ANTIBIOTIC

Organic Compound 69
 Others antibiotics:
– Penicillin notatum, P Chrysogenum == penicillin G
– Streptomyces venezuelas == chloramfenicol
– Streptomyces orchidactus == ceromycine
– Streptomyces spectabilis == streptovaricinum
– Streptomyces aureofaciens == chlortetracycline
– Streptomyces rimocis == terramycine
– Bacillus subtilis == bacitracinum
– Aerobacillus colistinus == colimycine
– Streptomyces erythreus == erythromycine
– Streptomyces lavandulae == framacelinum
– Aspergilus fumigatus == fumagillinum
– Streptomyces noursai == fungicidinum, nystatin,
mycosatic
70
– Penicillum griscofulvum == griseovulvum, grisovin
– Streptococcus kanamycaticus == canamycinum
– Streptomyces fradiae == neomycinum
– Streptomyces antibioticus == oleandimycinum, romicil
– Bacillus polymixa == polymixinum B.
– Nocardia lurida == ristocetinum
– Streptomyces ambofaciens ==spiromycinum
– Cephalosporium salmonynnematum == synnematin
– Streptomyces hachijoencis (Javaness)== trichomycin
– Bacillus bravia == tyrothricinum
– Streptomyces orientalis == vancomycinum
– Streptomyces griseus == streptomycin

71
 ANTIBIOTIC

2. 1. Penicillin

H H H S1
R–C–N–C6 C5 2C–(CH3)2
7 4 3
O=C N C–H
C=O
OH
penicillin
Organic Compound 72
 The Kind of Penicillin

The kind of
Name Formula
penicillin

Penicillin F pentenyl 2 CH2=CH2CH=CH2CH3

Penicillin G benzyl CH2C6H5
Penicillin K n-heptyl (CH2)6CH3
Penicillin X p-hidroxybenzyl (CH2)6C6H4OH-p
Penicillin O allylmerkophenylethyl CH2-S-CH2CH=CH2
Penicillin V phenoxymethyl CH2OC6H5

73
2.2. Chloramphenicol
O

NH–C – CHCl2
O2N- -CH – CH – CH2OH
OH

Organic Compound 74
2.4. Tetracycline

Me OH NMe2
* ** OH

OH
CONH2
OH O OH O

 Terramycin mempunyai gugus hidroksil

pada (**) dan oksitetrasiklin (auroemycin
bears) memiliki gugus klorin pada (*)

Organic Compound 75
 2.3. Streptomycine
R = -NHC=NH
OHC NH2
CH3
HO OH

HO
CH2OH R
CH3NH HO
R
OH OH

76
 2.5. Erythromycin ( C17H67O13N )
 Of the many classes of new antibiotic
compounds that have been discovered in
the past decade is a group of compounds,
produced by various strains of
Streptomyces that are unique in their
possession of many membered lactones
ring as their essential structure feature.
 Some of these are therapeutic value.
 One of the most important of the
“macrolides” as these lactones are called,
is erythromycin.

2.6. Neomycin
2.7. Canamycine 77
ORGANIC CHEMISTRY

1 ORGANIC COMPOUND

BIO ORGANIC
2
COMPOUND

Organic Compound 78
AMINO ACIDS

R C COOH

NH 2

Biomolecules

79
 Organic Reaction Mechanisms

 Organic reactions mechanisms has

classified biochemical reactions into four
categories:
 1. Group-transfer reactions
 2. Oxidations and reductions
 3. Eliminations, isomerizations, and
rearrangements
 4. Reactions that make or break carbon-
carbon bonds

Organic Compound 80
 Covalent bonds

 A covalent bond consists of an

electron pair shared between two
atoms.
 In breaking such a bond, the
electron pair can either remain with
one of the atoms (heterolytic bond
cleavage) or separate such that one
electron accompanies each of the
atoms (homolytic bond cleavage).

Organic Compound 81
 Homolytic Bond Cleavage

 Homolytic bond cleavage, which

usually produces unstable radicals,
occurs mostly in oxidation-reduction
reactions

Organic Compound 82
 Heterolytic Bond Cleavage

 Heterolytic C-H bond cleavage

involves either carbanion and proton
(H+) formation or carbocation
(carboniun ion) and hydride ion (H-)
formation.

Organic Compound 83
 Biologically Importan
Nucleophillic Groups

Nucleophiles are the conjugate bases

of weak acids
Organic Compound 84
 1. Group-transfer reactions

 Types of metabolic group-transfer: Acyl group

transfer involves addition of a nucleophile (Y)
to the electrophilic carbon atom of an acyl
compound to form a tetrahedral intermediate.
The original acyl carrier (X) is then expelled to
form a new acyl compound.
Organic Compound 85
 2. Oxidations and reductions

General
Base Alcohol NAD+

General
Ketone NADH
acid

NAD+ IS AN ELECTRON ACEPTOR (OXIDATOR); TWO ELECTRON FROM GENERAL

Organic Compound 86
BASE ARE TRANSFERRRED TO AN ELECTRON ACCEPTOR SUCH AS NAD+.
 In Living Systems

The electron-transfer process

connecting these half-reactions occurs
through a multistep pathway that
harnesses the liberated free energy to
form ATP.

Organic Compound 87
 Summary Reference:
1. Warn, J.R.W., Concise Chemical
Thermodynamics, Second Edition, Stanley
Thornes Ltd., United Kingdom, 1999,
page: 1-25, 52-78, 83.
2. McQuarrie, D.A., Simon, J.D., Physical
Chemistry a Molecular Approach,
University Science Books, Sausalito,1997,
page: 766-773, 787-790, 817-819, 853-
857.

Organic Compound 88