National University – HCMC

International University

SHOOL OF BIOTECHNOLOGY
SUBJECT: ORGANIC CHEMISTRY
LECTURER: PH.D HOÀNG LÊ SƠN
List of students:
NGUYỄN HẢI ĐĂNG BTUN08001
PHẠM VŨ ANH BTUN08004
NGUYỄN THỊ PHƯƠNG THÙY BTUN08032
VÕ TƯỜNG KHANH BTUN08048
NGUYỄN HỮU LỘC BTIU08147

 
 General Content:

INTRODUCTION

CLASSIFICATION

6 IMPORTANT GROUPS IN CHEMISTRY OF LIFE

INTERMOLECULAR FORCES

PHYSICAL PROPERTIES

REFERENCES
WHAT ARE FUNCTIONAL
GROUPS?

 In organic chemistry, functional

groups are specific groups of
atoms within molecules that are
responsible for the
characteristic chemical and
physical reactions of those
molecule.

 Functional groups define the

structure of a family of
compounds and determine its
properties.
CLASSIFICATION:

TWO TYPES OF CLASSIFICATION

Classification based on hetaroatoms

Classification based on the bond

 Classification based on
hetaroatoms
a.Hydrocarbon

b.Groups containing halogen

c.Groups containing oxygen

d.Groups containing nitrogen

e.Groups containing phosphorus and sulfur

  Classification based on the bond:

a.σ bonds (single bond)

b.π bonds
6 IMPORTANT GROUPS IN LIFE OF
CHEMISTRY
Hydroxyl
group

Carbonyl Carboxyl
group group

Amine Suflhydryl
group group

Phosphate
group
A. Hydroxyl group:
Definition:

A functional group which has one

oxygen atom bonded to one hydrogen
atom is called hydroxyl group.

-R-O-H (where R is any “alkyl” group)

Name Of Compound:

-Alcohols (their specific names usually end in -ol)

-Example: ethanol (ethyl alcohol)

Physical Properties:

-Boiling point: higher than alkanes (E.g: ethanol 78oC , ethane -162oC)

-Hydrophilic (water loving)

-Methanol, ethanol, propanol  soluble in water

-Butanol  moderately soluble in water

-Alcohols which containing 5 or more carbon atoms  effectively

insoluble in water
-Most of the common alcohols are colorless liquids at room temperature.
Ethanol, methanol, and isopropyl alcohols are free-flowing liquids.

-The higher alcohols-those containing 4 to 10 carbon atoms- are vicous

(oily).

-Some of the highly branched alcohols and many alcohols containing 12

or more carbon atoms are solids.
Chemical Properties:
1/ Undergo oxidation -> aldehydes, ketones, carboxylic acid:

2/ Dehydrates -> ankenes:

3/ React to form ester compound:

4/ Undergo Nucleophilic substitution:

Classification of purified water:

+Distilled water (water that has virtually all of its impurities

removed through distillation.)

+Double-distilled water

+Demineralized water (water that has its mineral ions remove)

 Health effects of water
- Water is needed to detoxify the kidneys and the liver
-Magnesium, calcium, fluoride, and other nutrients in water can help
to protect against nutritional deficiency
-If our body has a lack of water we will become constipated
- Your skin will look and be healthier
-You'll have less headaches and/or dizzy spells
-Safe water (safe for drinking and bathing) could prevent 1.4 million
child deaths from diarrhea each year
Application:

-Methanol can be used as an alcohol fuel

-Ethanol can be used as: beverage, alcohol fuel, solvent in medical
drugs, perfumes and vanilla, ethanol based-soap
-Alcohol gels have become common as hand sanitizers
B. CARBONYL GROUP:
Definition:

-A carbonyl group is a
functional group composed
of a carbon atom double-
bonded to an oxygen atom.

-Oxygen is more
electronegative than
carbon, and thus pulls
electron density away from
carbon to increase the
bond's polarrity.

Name of compound:
Aldehydes and Ketons.
CLASSIFICATION:
ALDEHYDE:

Physical Properties:
-HCHO, CH3CHO is gas, they have
strong smell, dissolve in water.

-Aldehyde has more than 3C is

liquid but slightly than water.

-HCHO (35%-40%) is called A

solution of Fomalin .

-Aldehydes have at least one

carbon attached to the carbonyl
group.
KETONES

Physical Properties:
-Ketones have two organic
groups attached to the carbonyl
group

-The carbonyl group is polar as

a consequence of the fact that
the electronegative of the
oxygen center is greater than
that for carbonyl carbon.

-Ketones are nucleophilic at

oxygen and electrophilic at
carbon.
Chemical properties:
ALDEHYDE: KETONES:
1.React with H2: 1.React with H2:

R-CHO + H2 --> R-CH2OH.

R-CO-R’ + H2 --> R-CHOH-R’
(Alcohol)
2. React with NaHSO3:

R-CHO + NaHSO3 --> R-CHOH

SO3Na
2. React with HCN:
3. React with HCN:
R-CO-R’ + HCN --> R-COH-R’
R-CHO + HCN --> R-CHOH
CN CN
We see that:
+1 -1
C + 2e --> C
Aldehyde is oxidizable.
ALDEHYDE:
 Oxidation-reduction reaction: KETONES:
The main reaction of Aldehyde is Tollens’  React with Br2:
mirror silver test:
CH3-CO-CH3 + Br2 --> CH3-CO-CH2Br +
HBr
R-CHO + 2[Ag(NH3)2]OH --> RCOONH4+
2Ag + 3NH3 + H2O DO NOT MAKE Br2 LOOSE ITS COLOR

 Benedict’s reaction (Cu(OH)2):

RCHO + 2Cu(OH)2 --> RCOOH + Cu2O

+ 2H2O

HCHO + 4Cu(OH)2 --> CO2 + 2Cu2O +

5H2O

 Bromine water reaction:

R-CHO + Br2 + H2O --> R-COOH + 2HBr

Biological Function:
GLUCOSE
(C6H12O6)

-Glucose is a carbohydrate, and is the most important simple sugar

in human metabolism. Glucose is called a simple sugar or a
monosaccharide because it is one of the smallest units which has
the characteristics of this class of carbohydrates.

-Glucose, also known as - grape sugar, blood sugar, or corn

sugar.

-The normal concentration of glucose in the blood is about 0.1%,

but it becomes much higher in persons suffering from diabetes.
-The living cell uses it as a source of
energy and metabolic intermediate.
-In animals and fungi, glucose is the
result of the breakdown of glycogen
-In plants the breakdown substrate is
starch.
-When oxidized in the body in the
process called metabolism, glucose
degrades to carbon dioxide, water
-Energy from glucose is obtained from
the oxidation reaction
C6H12O6 + 6O2 --> 6CO2 + 6H2O
Application:
-Aldehydes: HCHO: used to
produce plastic, dye,
pharmaceutical product,
medicine.

-HCHO 37% - 40% is Fomalin,

used to embalm a corpse.

-CH3CHO: used to produce

D.D.T (one kind of
insecticide).

-Ketones : used to synthetize

organic compound, polime,
clorofom, iodofom
C. Carboxyl group:
Definition:

-Carboxyl group is chemical

functional groups with one
carbon, one hydrogen, and two
oxygen atoms (COOH), usually
written -COOH or -CO2H .

-EX : acetic acid ( CH 3

COOH )
 THE IUPAC NAME OF A CARBOXYLIC ACID IS DERIVED FROM THAT OF THE
LONGEST CARBON CHAIN THAT CONTAINS THE CARBOXYL GROUP BY DROPPING
THE FINAL -E FROM THE NAME OF THE PARENT ALKANE AND ADDING THE
SUFFIX -OIC FOLLOWED BY THE WORD “ACID.” THE CHAIN IS NUMBERED
BEGINNING WITH THE CARBON OF THECARBOXYL GROUP.
Common name IUPAC name Chemical formula
Formic Acid Methanoic Acid HCOOH
Acetic Acid Ethanoic Acid CH3COOH
Propionic Acid Propanoic Acid CH3CH2COOH
Butyric Acid Butanoic Acid CH3(CH2)2COOH
Valeric Acid Pentanoic Acid CH3(CH2)3COOH
Caproic Acid Hexanoic Acid CH3(CH2)4COOH
Enanthic Acid Heptanoic Acid CH3(CH2)5COOH
Caprylic Acid Octanoic Acid CH3(CH2)6COOH

Pelargonic Acid Nonanoic Acid CH3(CH2)7COOH

Physical Properties:
Boiling point and melting point :
-Boiling point is the temperature at which vapor pressure saturated liquid
surface by atmospheric pressure .
-There are two factors that affect the boiling temperature and melting
point is the molecular weight organic compounds and Hydrogen bond of
this compounds .
Ex : acetic acid have boiling point at 118°C Formic acid have boiling
point at 100,8 °C (213,3 °F) .
Melting point g/mole
Formula Boiling
point
Propanoic C3H6O2 -21 °C (252 141 °C (414 74,08 g/mol
Acid K) K)
Melting point C4H8O2 -7,9 °C 163,5 °C 88,1051
(265,1 K) (436,5 K) g/mol
Chemical Properties:
Stability of the acid :
In the homologous organic acids , stability of acid decrease with the
increasing molecular weight:
H-COOH > CH3-COOH > CH3-CH2-COOH
Axit fomic Axit axetic Axit propionic
React with metal :
Ex:
CH3COOH + Mg  CH3COOMg + H2
React with basic :
Ex :
HCOOH + NaOH  HCOONa +H2O
React with salt:
Ex:
CH3COOH + CaCO3  (CHCOO)2Ca + CO2 + H2O

React with alcohols to give ester :

Ex:
CH3COOH + C2H5OH  CH3COOC2H5 + H2O
Haloenation

Ring substitution in aromatic acids

 Biological
function:
-A form of Vitamin C is called ascorbic acid and is a carboxylic acid
-Carboxylic acids that have very long, unbranched chains of 12-24
carbon atoms attached to them are called fatty acids , they are important
in the formation of fat in the body .
-Lactic acid is generated in muscles of the body as the individual cells
metabolize sugar and do work. A buildup of lactic acid, caused by
overexertion, is responsible for the fatigue one feels in the muscles by
such short-term use.
 Application:
-Carboxyl group used to produce chemical compounds .

-Many carboxylic acids are present in the foods and drinks we ingest,
like malic acid (found in apples), tartaric acid (grape juice), and oxalic
acid (spinach and some parts of the rhubarb plant)

-Carboxylic acids are also very important industrially. Perhaps one of the
most important industrial applications of compounds with carboxyl
groups is the use of fatty acids--carboxyl groups attached to long carbon
chains--making soaps, detergents, and shampoos . Carboxylic acids are
also important in the manufacture of greases, crayons, and plastics .
D. Amine Group:

Definition:

-Amines are organic compounds which are composed from

ammonia by replacing one, two or three of the hydrogen atoms
on an ammonia molecule by alkyl or aryl group.
 Classification:

Primary amines:

Secondary amines:

Tertiary amines:
Name Of Compound:

AMINE
 Physical
-Primary andProperties:
secondary amines can form hydrogen bonds to each other
and water. Tertiary cannot form hydrogen bonds to each other but can
form hydrogen bonds to water.

-The boiling point: in the isomers of amine, the boiling point of primary
amines is highest and tertiary amines is lowest.

-Amines are soluble in water.

-All of the amines have stench odor.

Chemical Properties:

Basicity:
Amines are organic derivatives of ammonia, so basic properties of
amines like ammonia.
NH3 + H2O ↔ NH4+ + HO-
RNH2 + H2O ↔ RNH3+ + HO-
Amines react with acid (1):
Ammonium salts react with bases:
CH3NH3Cl + NaOH → CH3NH2 + NaCl + H2O

C6H5NH3Cl + NaOH → C6H5NH2 + NaCl + H2O

Halogenation

C6H5NH2 + 3Br2 → C6H5NH2(Br)3 + 3HBr

Sulphurization

C6H5NH2 + HOSO3H → H2N-C6H5-SO3H + H2O

Amines react with nitrous acid:
Primary amine:
R-NH2 + HO-NO → R-OH + N2↑ + H2O
(alcohol)
Secondary amine: (2)

-Tertiary amine does not react with nitrous

acid
Biological Function:
-Linear chains of amino acid build block of proteins
Application:
-Many drugs are designed to mimic with the action of natural amine
neurotransmitters.
Ex: glucosamine is a building block of
proteoglycans which are essentially
protein molecules.
5.Sulfhydryl Group:
Definition:
- Sulfhydryl or Thiol is a
functional group consisting
one sulfur atom bonded to
one hydrogen atom.
Name of compounds:

-The name of compounds containing sulfhydryl

groups are formed by adding the prefix “- thiol”.
Physical Properties:
Odor :
-The odor of thiols is often strong and repulsive, particularly for
those of low molecular weight .
-However, not all thiols have unpleasant odors.

-Ex : Propanethiol (C3H7SH) is found in freshly sliced onion

Boiling Points & Solubility:

-Thiols show little association by hydrogen bonding , with both water

molecules and among themselves .

-Hence, they have lower boiling point and are less solube in
water and other polar solvent than alcohols of similar
molecular weight. They boil at considerably lower temperatures:
 H2O..........100 H2S……….-61
CH3OH…..64.7 CH3SH…….7.6
C2H5OH….78.3 C2H5SH……34.7
• Chemical propeties:

S-alkylation
Thiols, or more particularly their conjugate bases, are readily alkylated
to give thioethers:
RSH + R'Br + base → RSR' + [Hbase]Br

Acidity
The sulfur atom of a thiol is quite nucleophilic, rather more so than the
oxygen atom of an alcohol. The group and its corresponding anion are
readily oxidized by reagents such as bromine to give an organic
disulfide (R-S-S-R).
2R-SH + Br2 R-S-S-R + 2HBr
Redox:

-Thiols, especially in the presence of base, are readily oxidized by

reagents such as iodine to give an organic disulfide (R-S-S-R).

-2 R-SH + Br2 → R-S-S-R + 2 HBr Oxidation by more powerful

reagents such as sodium hypochlorite or hydrogen peroxide yields
sulfonic acids (RSO3H).
-R-SH + 3H2O2 → RSO3H + 3H2O Thiols participate in
thiol-disulfide exchange:

-RS-SR + 2 R'SH → 2 RSH + R'S-SR' This reaction is

especially important in nature.
Biological Function:

Cysteine (Cys)

-As the functional group of the amino

acid cysteine, the thiol group plays an
important role in biology: amino acid.

-When the thiol groups of two cysteine

residues (as in monomers or constituent
units) are brought near each other in the
course of protein folding, an oxidation
reaction can generate a cystine unit
with a disulfide bond (-S-S-).

-A physical manifestation of cysteine-

cystine equilibrium is provided by hair
straightening technologies.
-Sulfhydryl groups in the active
site of an enzyme can form
noncovalent bonds with the
enzyme's substrate as well,
contributing to catalytic
activity.

-Active site cysteine residues are

the functional unit in cysteine
proteases.

-Cysteine residues may also react

with heavy metal ions because
of the high affinity between the
soft sulfide and the soft metal.
Application:
-Enzyme Ficin (EC 3.4.22.3) , a thiol protease, presents in the latex of
some fig species (genus Ficus, family Moraceae) From the latex of
this fig, we have received the preparation of ficin and determined
some factors which effect on the activity of this enzyme such as pH,
temperature , substracts.
6. PHOSPHATE
GROUP:

Definition: (PO43- )

- An anion formed by dissociation of

H3PO4
- Structure: one central phosphorous
atom attached with four oxygen
atoms in a tetrahedral arrangement.
Name of compound:
-Organic Phosphate

-Eg: Name of some compounds:

Physical Properties:
-PO4 3-

-general mass: 94.973 g/mol

-For example: ATP

 Formula : C10 H16 P3O13 N5

 Molar mass : 507.181 g/mol

 Highly soluble in water

 Quite stable in solutions between pH 6.8–7.4 but is rapidly

hydrolysed at extreme pH
 Best stored as an anhydrous salt.
Chemical Properties:
- The phosphate ion is derived from phosphoric acid by
electrolytic dissociation reaction in 3 steps:

H3PO4 H+ + H2PO4_

H2PO4_ H+ + HPO4 2_

HPO4 2_
H+ + PO4 3_
 Why phosphate group show the characteristic
of an acid?
-Because the oxygen atom with double bond and
phosphorous atom are electron withdrawal .

-We can use H3PO4 to make some examples.

-H3PO4 is an average acid, it can make the reaction with

base, salt of weaker acid.
 React with Base:
H3PO4 + NaOH = NaH2PO4 + H2O
(the ratio of this reaction : 1:1)

H3PO4 + NaOH = NaHPO4 + H2O

(the ratio of this reaction: 1:2)

H3PO4 + NaOH = Na3PO4 + H2O

(the ratio of this reaction: 1:3)
React with Salt of weaker acid:
2H3PO4 + 3CaCO3 = Ca3(PO4)2 + 3 H2O + 3CO2
Biological Function:

-Phosphate can be found in ATP, ADP, and AMP, and can be released
by the hydrolysis of ATP or ADP.
What is ATP?

-An energy – rich molecule in all cells especially in

muscle cell.

-In cell biology, ATP play an important role as a coenzyme

in energy transfer.
Application:

- Phosphate is a component to build the phospholipids in lipid bilayer.

Function of lipid bilayer:

-A barrier between the transport inside and outside the

cell.

-Polar molecules and ions are transported across cell

membranes encapsulated within molecules called
ionophores.

-Phosphate in the cell has 2 main functions in biology:

Storage energy and Signaling.
Intermolecular Forces:
Definition:

-All matter is held together by

force. The force between
atoms within a molecule is a
chemical or intramolecular
force. The force between
molecules is a physical or
intermolecular force.
CLASSIFICATION:

• Dipole-dipole interaction
• Hydrogen bonding
• London forces
• Ion-dipole forces
LONDON DISPERSION FORCES

-The weakest of the imtermolecular forces.

-London forces are the attractive forces that cause

nonpolar substances to condense to liquids and to
freeze into solids when the temperature is lowered
sufficiently
ION-DIPOLE

-An ion-dipole force is an attractive force that results

from the electrostatic attraction between an ion and
a neutral molecule that has a dipole.

-A positive ion (cation) attracts the partially negative

end of a neutral polar molecule.

-A negative ion (anion) attracts the partially positive

end of a neutral polar molecule
Dipole-dipole interaction
• Dipole-dipole interactions are the forces that occur between
permanent dipoles of two polar molecules.
• Dipole-dipole forces exist when molecules are neutral polar (the
partial positive charge on one molecule is attracted with the
partial negative charge on another molecule)
Hydrogen bonding:
-Hydrogen bond is interaction between a hydrogen
atom bonded to N, O, F with a nonbonding electron
pairs on an N, O, F atom on another molecule
Comparison between intermolecular forces
and intramolecular forces :

Intramolecular forces Intermolecular forces

which are existed within which are existed between
molecules and influence moleculars and influence
on chemical properties. on physical properties.
Covalent bonds that join Intermolecular forces hold
atoms together in together most organic
molecules. compounds to each other
The ionic bonds that join
ions together in ionic
compounds
The metallic bonds found
in solid metals.
 Ionic Covalent Metallic Intermolecular

Bond strength Strong Very strong Variable Weak

Comparison table of the propertiesstrength,
of subtances with intermolecular
generally
forces and intramolecular forces: (1)
moderate

Hardness Moderate to high Very hard, brittle Low to moderate; Crystal soft and somewhat plastic
ductile, malleable

Electrical Conducts by ion Insulators in solids Good conductors; Insulators in both solid and liquid states
conductivity transport, but only and liquid states conducts by
when liquid or electron transport
dissociated

Melting point Moderate to high Low Generally high Low

Solubility Soluble in polar Very low solubility Insoluble except Soluble in organic solvents
solvents in acids or alkalis
by chemical
reaction

Examples Most minerals Diamond, oxygen, Cu, Ag, Au, other Organic compounds
hydrogen, organic metals
molecules
PHYSICAL PROPERTIES:
Melting Point:
-The temperature that can change the solid to liquid by the
application of heat.

-In melting, the energy is needed for overcoming the attractive

forces in crystalline solid.

- The characteristic of melting point is figure and indentify pure

compounds , elements.
- The higher in melting point, the stronger of intermolecular force.

- When the covalent molecules have the same weight, the melting
point depends upon the identify of the functional group.
-If the compounds have the same functional group, the higher melting
point is depended on its symmetry.

-Symmetry is used to determine the melting point of compounds, having

the same functional group and similar molecular weights, but very
different shapes.
Boiling point:

- The temperature at which the transition from liquid to the gaseous

phase occurs in the pure substance at fixed pressure.

- Boiling point needs energy to overcome the attractive forces in liquid

state.

- Similar to melting point, the stronger of intermolecular forces, the

higher melting point.
-Consider the examples below which illustrate the effect of size and
polarizability on boiling points.
SOLUBILITY:
Definition:

Solubility is the property of a solid , liquid , or gaseous chemical

substance called solute to dissolve in a liquid solvent to form a
homogeneous solution . The solubility of one substance in another is
determined by the balance of intermolecular forces between the
solvent and solute, and the entropy change that accompanies the
solvation.
In dissolving a compound, the energy needed to break up the interactions
between the molecules or ions of the solute comes from new interactions
between the solute and the solvent.
polar dissolves polar
nonpolar dissolves nonpolar
likes dissolves like

ex : a very polar ( hydrophilic ) solute such as urea is very

soluble in highly polar water, less soluble in fairly polar
methanol , and practically insoluble in non-polar solvents
such as benzene. In contrast, a non-polar or lipophilic
solute such as naphthalene is insoluble in water, fairly
soluble in methanol, and highly soluble in non-polar
benzene.
-An organic compound is water soluble only if it contains one polar
functional group capable of hydrogen bonding with the solvent for
every five C atoms it contains .To dissolve an ionic compound, the
strong ion-ion interactions must be replaced by many weaker ion
dipole interactions.
•REFERENCE:
PHOSPHATE:
•http://wapedia.mobi/en/Organophosphate
•http://en.wikipedia.org/wiki/File:Trisodium_phosphate_3D.jpg
•http://en.wikipedia.org/wiki/File:0-phosphate-3D-balls.png
•http://www.chemdrug.com/databases/dataimg/7/62657.png
•http://fiehnlab.ucdavis.edu/Metabolite-Library-2007/124.png
•http://www.ecplaza.net/search/0s1nf20sell/tripotassium_phosphate.html
•http://www.ecplaza.net/search/0s1nf20sell/tripotassium_phosphate.html
•http://vi.wikipedia.org/wiki/Adenosine_triphosphate
1.kentsimmons.uwinnipeg.ca/cm1504/atp.htm
2.http://static.howstuffworks.com/gif/rd/chemical-elements-of-fertilizers0.jpg
PHYSICALPROPERITES:
•http://en.wikipedia.org/wiki/Melting_point
•http://en.wikipedia.org/wiki/Boiling_point
•http://chemistry.uca.edu/faculty/manion/2401/2401res/chap3.pdf
CARBOXYL GROUP:
•http://www.bookrags.com/research/carboxyl-group-woc/
•http://www.tutorvista.com/content/chemistry/chemistry-iv/oxygen-ii/acidity.php
•http://www.cem.msu.edu/~reusch/VirtualText/crbacid1.htm
HYDROXYL GROUP:
1.(1) http://en.wikipedia.org/wiki/Hydroxyl
2.(2)
http://upload.wikimedia.org/wikipedia/commons/thumb/8/88/Hydroxyl3D.png/200px-Hydrox

(3)http://www.britannica.com/EBchecked/topic/13366/alcohol
(4)http://en.wikipedia.org/wiki/Alcohol
(5)http://www.ncbi.nlm.nih.gov/pubmed/31434
SULHYDRYT GROUP:
http://en.wikipedia.org/wiki/Sulfhydryl_group
http://www.arkema-inc.com/index.cfm?pag=123
AMINES:
1. http://en.wikibooks.org/wiki/Organic_Chemistry/Amines#Properties
•http://dl.clackamas.cc.or.us/ch106-05/nomencla.htm
•http://en.wikibooks.org/wiki/Organic_Chemistry/Amines#Properties
•http://wapedia.mobi/en/Amine
•http://bhptemp.mypcat.com/mihirkanani/pcat-gifs/products-small/quinine-sulphate_106781
INTERMOLECULAR FORCES:
http://en.wikipedia.org/wiki/Intermolecular_force
http://www.chem.purdue.edu/gchelp/liquids/iondip.html
http://en.wikipedia.org/wiki/Hydrogen_bond
http://www.webchem.net/notes/chemical_bonding/dipoled
http://en.wikipedia.org/wiki/Van_der_Waals_force
corvallis.k12.or.us/cvhs/kirscha/Exploring Intermolecular
Forces...