Where is the word of organic came from ?

The basic word for organic came from the word organ We knew, the word organ have close relationship with the word Organism
Have you ever come across the word organ/organism .?

Therefore, organic chemistry is the study chemistry of carbon compounds, but also it also included the compounds containing, hydrogen, oxygen, nitrogen, and other elements such, halogen, phosphrous and sulphur, as shown in the following periodic table;

The study the compound of these elements

Examples Of Organic Compounds:

Compounsd
Benzene Vinegar Sucrose Chloroform Urea Protein(alanine)

Formula
C 6H 6 CH3COOH C12H22O11 CHCl3 CO(NH2) C 3 H 7 O2 N

Elements Present
C, H C, H, O C, H, O C, H, Cl C, H, O, N C, H, O, N

Can any one in class explain what are some of the uses of the above compounds .. ?

Before we discuss futher about the chemical bond, we should know of the following concept: 1. electronic configuration of an elements 2. Octet configuration

J.McMurry p. 4

What is the electronic configuration meant.? e

1H

1 2

A particular arrangement of electron in the orbitals of an atom

2,1
e e 1s 2s,2p

2He 3Li

4Be

e
e
5B

e e

2,2

11Na

2,8,1

e e e

2,3

e
e e

e e e

6C

2,4 e

e e e e e e e 2.6

8O

J.McMurry p. 5

1S

2S

2p (pxpypz)

1H

= = 1S1 2He = 1S2 = 3Li = 1s22S1 = 4Be = 1s22S2 = 5B = 1s22S22p1 = 6C =1s22S22p2 = 7N =1s22S22p3 = 8O =1s22S22p4 = 9F =1s22S22p5 = 10Ne=1s22S22p6=

2.8 Octet

Write the configuration of the following elements

1. 2. 3. 4.
13Al

Aluminium Cromium Manganese Copper

= 1s2 2s2 2p6 3s2 3p1

24Cr 25Mn
29Cu

= 1s2 2s2 2p6 3s2 3p6 4s13d5 ( x 4s2 3d4 ) = 1s2 2s2 2p6 3s2 3p6 4s23d5
= 1s2 2s2 2p6 3s2 3p6 4s13d10 ( x 4s2 3d9 )

2 Filled > 2 half- filled > 1 filled 1 not half

Reaction between AB + C == > D Take place. Why . ?

The Chemical reaction take place inorder the system becomes:
Eenergy Level AB + C

--------H reaction AC + B

1. More order . ? 2. More stable . ?

--------------Reaction Coordinate

Atom at distance

Energy
Atom Bonded In Molecule

Ikatan Perkahwinan Menjadikan Individu Lebih Tenang/Stabil/Tersusun

Weaker bonded

Covalent Antara lelaki/lelaki Antara Perempuan/perempuan

Stronger bonded Antara lelaki/perempuan Ionic/Heterovalent

A + A == > B AB+C == > AC + B

(H+H ==> H2) (H2+ O2== > H2O)

1. Sharing electron among the elements ( covalent )

2. Give/received the electron(s) == > ions 3. Attraction between different ions ( ionic ) 4. Restructuring the electronic configuration in the molecules Breaking down the bonds = (required energy) Rearrangement the pair(s) of electron(s)/Bonding Formation of new bonds (released energy)

Base on your experiences, can you name the types of bonding in chemistry ?. There are: 1. Ionic bonding

2. Covalent bonding
3. Metallic bonding 4. Hydrogen bonding

J.McMurry m.s 7

How does the ionic bond formed ... ? Can any one in class explain it.. ?
By transfering/receiving an electron of electropositive and electronegative atoms

Example Na (electropositive) and F (electronegative)

What is the configuration electron of Na atom ?
11Na

Electropositive element, (Na) gives up one valence electron, to have octet configuration and form a positive charge Na+ = 10
Octet Configuration Stable

What is the configuration electron of F atom ?

9F

Electronegatif element, (F) received one valence electron, to have octet configuration and form a negative charge
10F

Octet Configuration Stable

Different charge Of (Na+) and (F-) attract together by electrostatic force to form ionic bond

Na+

F-

Na --- F Ionic bond

Ionic compound

Electrostatic attraction

Electropositive element

Electronegative element

( Na )

2.8.1

F ( 2.7 )
receive 1 electron Cl- ( 2.8 ) (octet/stable)

Give up 1 electron Na+ 2.8 (Octet/stable) Different charge Electrostatic force Na --- F (Ionic Bonding

J.McMurry, p11

The word covalent is made up of two basic words, What are they ..? They are CO + Valent ( valence ) What is the meaning of Co and valence .. ? Co meant sharing and valence related to valence electron What is the meaning covalent bond than .. ? Bond formed by sharing of valence electron by any atoms so that
each one atom to achieved an octet stable configuration ( Configuration od noble gas) .. .. .. .. O :: C:: O H:O:H : F: : F : .. .. .. .. O=C=O Example: H -- O -- H F -- F

J.McMurry, p11

Electronic configuration for Ne (noble gas) = 1s2 2s2 2p5

Electronic configuration for F = 1s2 2s2 2p5 Less one electron

F atom would share one electron to another F atom to achived, octet (stable)configuration and form a covalent bond:

.. Sharing electron .. :F. .F: .. ..

.. .. : F: : F : .. ..
FF Covalent Bond

There are two types of covalent bonds;

i) Sigma () bond ii) Pi ( ) bond

J.McMurry, p11

What do you understand by sigma () bond? Is a covalent bond formed by orbitals overleapping end to end of the following orbitals: i) two s orbitals ii) 1 s orbital and 1 p orbital iii) 2 p orbitals ( head-head or end-end ) Its electron density is concentrated between the nuclei of the bonding atoms. Study the following diagrams given

Head-to head overleap bond

Atomic Nucleous

+
S orbital S orbital

bond
Electron density

+
S orbital p orbital

bond

+
p orbital p orbital

 bond

bond

bond
Electron density

J.McMurry, p17

Does any one can explain what is pi () bond meant.? pi () bond is a covalen bond formed by overleapping of side-by-side of P orbitals. Its electron density is concentrated above and below the plane of the nuclei of the bonding Exame the following diagrams:

py Orbital

bond
pz Orbital
Electron density

bond bond
px Orbital

Side by side overleap

Electron Density

Draw the structure of 2-methyl-2-butene and identify the sigma () and pi () bond in the molecule

J.Mcmurry p, 8-9

Also known as electron dot structure Have you ever heard the terms Lewis Structure . ? A concept to show the structure of a molecule by using dots and dashes to show the valence electrons and shared pairs of the electrons Can any one give an example of a lewis Have you ever heard the terms Lewis Structure . ?
Example: Hydrogen atom have 1 valence electrons. What is the lewis structure of carbon

Example: carbon atom have 4 valence electrons. What is the lewis structure of carbon

.
.

Example: one molecule of water was formed as result the combination between 2 atoms of H and one atom of oxygen. H atom has 1 valence electron and oxygen have 6 valence eklectrons.

Can any one write the chemical and lewis structure of the above statement ?.
H2 + o2 H2O

.. 2H. + . O .
..

H- O - H
..

..

Can any in class write the lewis structure of NH3? How many valence electron N have ? N have 5 valence electrons Can any in class write valence electronic for N ? . :N. . Now, Can any in class, write the lewis structure of NH3

H : :N:H : H

or

H I : N - H I H

Please, write the lewis structure of the following molecules/compounds

i)

Common salt

ii) Chloroform iii) Ethanol

iv) Vinegar

Majority of the molecules are not 100% ionic nor 100% covalent The molecules which not 100% ionic ( fully charge) or 100% covalent (electronically symmetrical) are called polar molecule (partially charge) What is the meaning of polar covalent bond .? A bond in which electrons are not shared evenly (the density of the electron is not evenly distributed through the molecule and hence is a polar molecule Example: Electrons are located more on F atom rather than in H ;Hel < Fel Hence at F is more negatif charge and at H is more positive charge; .. H --- F : .. What is/are the factors that determine covalent bond become a polar bond ?
The electronegativity of the elements that form the covalent bond/molecule

Different element have different electrogenativity, Example:

Element H Li Be B C N O F Electronegativity 2.1 1.0 1.5 2.0 2.5 3.0 3.5 4.0 Element

Electronegativity
0.9 1.2 1.5 1.8 2.1 2.5 3.0

Na Mg Al Si P S Cl

When a covalent molecule formed between two different element having different electronegativity, such as: H (2.1) and F ( 4.0)

the density of electron in both end of the molecules are not even. As result the polarity both end are different.
The end with higher density of electron will be negative charge and the other end will positive charge

.. H --- F : .. The symbol + indicate partially (+) charge and indicate partial (-) charge

Or

H ------ F

The symbol --- > indicate the direction of polarization

If a molecules formed of different element hqaving different electronegativity the molecules should be polar.

Example
O-O, C-C, ( Less/not polar ) C- H, C- Cl, N - F, O-H, O-Cl ( polar )

At end of this disussion students should be able to: 1. Define what hybridization is . ? 2. Explain how the formation of hybridization sp3 in carbon 3. Explain how the formation of hybridization sp2 in carbon 4. Explain how the formation of hybridization sp in carbon

J.Mcmurry p 12

What do you meant by hybridization ? The mixing of different types of atomic orbital to produce a set of equivalent hybride orbital
Example: s orbital mix with 1 p orbital == > sp orbital
s + p sp

 There are 3 types of hybridization can occur in carbon: 1. Sp3 hybridization 2. Sp2 hybridization 3. Sp hybridization

J.Mcmurry p 14

What is the atomic number of carbon?

six

Can you write the electronic configuration of carbon atom..?

2,4

or

1S2

2S2

2px2 2py

2pz

How many unpaired valence electron in the configuration available for bonding formation? What is the normal valence electrons of carbon in organic compounds?

Two (2)

four (4)

How does the configuration electrons in carbon should change, inorder their valence electron becomes 4?
One of the electron from 2s orbital should move to py orbital

How?....
When carbon atoms, received enough energy, one electron from 2s orbital will move (jump) to 2py orbital, as shown, below:

1s

2s

2px

2py 2pz

And now their electronic configuration becomes :

**
1s 2s 2px 2py 2pz

Excited

How many unpaired electron available for formation bonding now that carbon atom have?

What is the angle between axis Px, Py and Pz

Can any one of you draw the axis of p orbital ? How does its look like ?
py

90 o

px pz

If carbon atom using 3p atomic orbital for bonding, what should be the angle of the bonding?

90o

Do you agree that most compouds involving carbon atom has bond angle of 90o? .. What is your comman? What is actually happen to the 4 unpaired electrons in carbon atom ? ..
All four unpaired electrons are mix/combine together to form new 4 orbitals which equivalent each other 1s orbital + 3 orbital p == > Hybride == > Sp3 orbital

No

The original S and p characteristic lose it identity

= >sp3

New identity orbitals is

4 new equilvalence orbital special characteristic Equivalent in angle, Equivalent in bond strength

The process of transfer electron from s -- > p followed by the combine of four orbital to form special 4 equivalent orbital is known as Hybridization

If not 90o, what should be the shape of the new orbital..?

The sp3 have following shape?

**
Excited

3p

Sp3 (tetrahedral)

The 4 unpaired electron will shared by one electron each from hydrogen atom to form CH4

Methane ( CH4 )

C ( sp3)

J.Mcmurry, p 18

J.Mcmurry p 16

As mentioned before, After 1 el (2s) move to 2p the electronic configuration in carbon atom becomes :
1s 2s 2px 2py 2pz

**

Excited

How does the sp2 hybrid in carbon is form?

Can any one in class proposed How the formation of Sp2 hybridization in carbon ?
1s orbital and 2 p orbital will hybrid each other to form sp2 hybrid;

sp2

C sp2

C sp2

Overleaping 2 (C sp2)

Example:H2C=CH2
bond

bond

or

Overleaping of 2 (Csp2)

Sp2

Sp2

H2C=CH2

or

As mentioned before, After 1 el (2s) move to 2p the electronic configuration in carbon atom becomes :
1s 2s 2px 2py 2pz Excited

**
How does the sp hybrid in carbon is form ..? Can any one in class proposed How the formation of sp hybridization in carbon ?

1s orbital and 1 p orbital will hybrid each other to form sp hybrid;

sp 1s 2s 2px 2py 2pz Excited

**

Discuss the formation of hybridization in: i) NH3 ii) H2O iii) BeCl2

At end of this disussion students should be able to:

1. Discuss how a bond is beeing broken 2. Discuss homolytic, heterolytic, nucleophile, electrophile, carbocation and carboanion. 3. Explain define distillation 4. Explain the differences of simple distillation and fractional distillation

How does a covalent bond breaking in the chemical reaction. ?

In the chemical reaction the covalent bond beak by two ways: i) Homolytic ii) Heterolytic

Let we discuss each types in relatively detail

What is the homolytic meant ?

homolytic made up of homo (same) and lytic (loosing) ?

So homolytic mean, a bond that break in an electronically symmetrical way, I.e: It meant, one electron remains with each product fragment to form a free radical species, as shown below A B === > A + B
(Free radical)

Example:
CH4 == > CH3 + H
H .. H : C .. H : H .. H ==> H :C. .. H + H.

What is the free radical ? Can any one give the definition of a radical .. ?

Radical is a species which have unpaired electron ..

Radical is sp2 hybridized and planar

The orbital of radical is not empaty but it containsthe odd electron

it is a reactive species

What is the heterolytic meant ?

heterolytic made up of hetero (different/not same) and lytic (loosing) ?

So heterolytic is bond break down in an electronically unsymmetrical way It meant that both electrons remain with one product fragment, living the other one with a vacant orbital

This process produced of a pair of ions, i.e; (cation and anion )

Can any one in class suggested the mechanism involved.?

The mechanism of breaking down of the bond are given below: A : B === > A+ + :B ( A: + B+ )
Ion ( cation/anion )

If the process invloved carbon ( alkyl group ) a carbocation/carboanion is produce, as shown below: + R C -->-- X Example: CH3 .. CH3 CH3 C ---- Cl : === > CH3 C + + CH3 .. CH3
(Carbocation)

=== > R C +
(Carbocation)/Canion

+ X( anion )

Cl( anion )

+ === > R C+ MX+

( anion )

R C --<-- MX

Example

(Carboanion)

(CH3)3 C :

Cl === > (CH3)3 C+

(Carbocation)

Cl( anion )

Carbocation is also known as carbonium ion

What is carbonium ion. ?

Carbonium ion is a species that contain a carbon atom bearing a positive charge The (+) charge carbon atom is bonded to other atoms and it has no non-bonding electron.

It is sp2 hybridized with a planar structure and bond angles of about 120o
The unhybridized p orbital is vacant and lies perpendicular to the plane of the C-H bonds

Has only six electrons in its valence shell

At end of this discussion students should be able to: 1. Define what is the carboanion 2. Define and give example of eletrophile and nucleophile 3. State the differences of nucleo/electro phile 4. Explain define distillation 5. Explain the differences of simple distillation and fractional distillation

What is the Carboanion ? Carboanion has a trivalent carbon atom that bears a (-) ve charge There are 8 electrons around the carbon atom ( 3 bonds and one lone pair )

It is a rich electrons
It is strong nucleophile ( lewis base ) The carbon atom is sp3 hybridized and tetrahedral in shape One of the tetrahedral positions is occuoied by an unshared lone pair of electrons

Electron-deficient compounds have tendency to undergo chemical reaction inorder to complete their valence electron becomes octet. How ? Electron-deficient compound will react with a species (compound) that has one or more unshared valence electron pairs Can any one give the example . ?

.. :F: .. I :F -- B .. I :F: ..

.. + [ : F ; ]- == > F B -- F .. I F

In above reaction, the electron dedficient compound acts as a Lewis acid ( Electron acceptor )

The species that provides the electron pair act as Lewis bes. ( Electron donor )
In organic the lewis acid terms known as an electrophile and lewis bes known as nucleophile .. :F: .. I :F -- B .. I :F: ..
Lewis acid (electrophile)

.. + [ : F ; ]- == > F B -- F .. I F
Lewis bes (nucleophile)

What is electrophile meant .. ?

Electrophile made up of two words

( Electro + phile )

Electro mean is related with electron Phile mean loving Loving electron

What is nucleophile meant .. ?

Nucleophile made up of two words

( Nucleo + phile ) Nucleo mean is related with nuclei Phile mean loving

Loving nuclei

H
H N: H +

F
B F F === > H

H
N H

F
B F F

Nucleophile electrophile

..

.. H

CH3 O : + H ..
Nucleophile

C H

Cl === > CH3 O C H + Cl.. H

electrophile

G.I Brown, p 56

What do you meant of distillation .?

A process to separate a liquid mixture ( from liquid/ liquid) by boiling of the mixture in distilation apparatus.

What do you understand of fractional distillation ? Fractional distillation is a procedure for separating liquid components of a solution that based on their different boiling points

Sections Of Apparatus
1. Sampel 2. Heating Mentel 3. Flask

4. Fractionating column
5. Condenser 6. Collection Bottle

Can you list out the differences between these two proceses?

Simple Distillation

Fractional Distillation

Gases B.P < 20oC, (C1-C4) hydrocarbon, used fuels & reactants to make plastics

Gasoline(napthas) 20-200oC (C5C12) hydrocarbon, Used as motor fuels & Industrial solvents Karosene 175-275oC (C12-C16) hydrocarbon, Used for lamp oil, diesel starting material for catalytic cracking, Fuel oil 250-400oC (C15-C18) hydrocarbon, Used for catalytic cracking, heating oil, diesel fuel)

The more volatile fraction which consist of smaller molecules, are received from higher up the columm

Less volatile factions from lower columm

Lubricating oil < 350oC (C15-C20) hydrocarbon, Used as lubricatants),

Residue (asphalt) (>C20 hydrocarbon)

G.I Brown, p 83-85

Fraction
Residue Heavy Gas-oil light. Light Lubrication oil Light gas-oil

Temp oC
>400 300-400 300-400 250-300

No Of Carbon
25 18-25

Use
Heavy fuel oil & Butumen Fuel.Lubrication. Paraffin Medicinal paraffin

13-17

Fuel oil Diesel enginers Fuel oil Trctor & Jet-engines Solvent & Raw material

Kerosine (paraffin oil) Naphtha Petrol (gasoline) Petroleum ether

190-250

11-14

100-200 40-180 40-60 60-80 < 40 1-5 5-10

Fuel Solvent

Gas Fraction

Gaseous Fuel Source of Alkanes

You are given a mixture containing C2H6, C10H22, C40H80. Discuss how the mixture can be saperated ?

Organic Compounds Hydrocarbon Derivatives Of Hydrocarbon

(Aliphatic & Aromatic)

Saturated

Unsaturated

Aromatic

Straight Chain Cyclo Chain

Alkyl halides Alcohols

Ethers

Ketones

Carboxylic Acids

Aldehydes

amines

Acid

Acid Anhydrides

Acid Halides

esters

Nitriles

amides

What is the functional group ?

An atom (or group of atoms) that is part of a larger molecules and has a characteristic chemical reactivity. The functional group determine the chemical properties of the compound.

The examples of functional group are given in the following table:

Compounds Alhyl Halide, Ether, Alcohol, Aldehyde, Ketone, Carboxyalic acid, Ester Amine, Amide

Fungsional gp G.Formula Example Halogen -O-OH -CHO - CO - COOH - COO - NH2 -CONH2 RX ROR ROH RCHO R-CO-R RCOOH RCOOR RNH2 RCONH2 CH3Cl CH3OCH3 CH3OH CH3CHO CH3COCH3 CH3COOH CH3COOCH3 CH3 NH2 CH3CONH2

R.Chang, p 460-462

Type Of Glass

Composition (mass)

Properties & Uses

Pure Quartz Glass

100 % SiO2
60-80% SiO2, 10-25% B2O3, Littke Al2O3

Low thermal expansion, Transparent (Optical research)

Low thermal expansion, Transparent ( Lab Ware, House hold ware ) Attck by chemical, Transparent, Sensitive to thermal shock ( Windo glass, Bottles) High Melting, (Cooking ware)

Pyrex Glass

Soda-lime

12% Na2O, 12% CaO, 76% SIO2

Aluminosilicate

5% B2O3, 10% MgO, 10% CaO 20% Al2O3, 55%SiO2 10% Na2O, 20%PbO, 70% SIO2

Lead alkali

High refractive index; (Lenses, Decorative glass) Low Coefficient of thermal expension; (Laboratory ware, cooking utensils Compatible with bone,( Coating on srgical implants

Borosilicate

5% Na2O, 3% CaO, 16% B2O3, 76% SiO2 24% Na2O, 24% CaO, 6% P2O5, 46% SiO2

Bioglass

R.Chang, p 460-462

Type Of Glass

Composition (mass)

Properties & Uses

Pure Quartz Glass

100 % SiO2
60-80% SiO2, 10-25% B2O3, Littke Al2O3

Low thermal expansion, Transparent (Optical research)

Low thermal expansion, Transparent ( Lab Ware, House hold ware ) Attck by chemical, Transparent, Sensitive to thermal shock ( Windo glass, Bottles) High Melting, (Cooking ware)

Pyrex Glass

Soda-lime

12% Na2O, 12% CaO, 76% SIO2

Aluminosilicate

5% B2O3, 10% MgO, 10% CaO 20% Al2O3, 55%SiO2 10% Na2O, 20%PbO, 70% SIO2

Lead alkali

High refractive index; (Lenses, Decorative glass) Low Coefficient of thermal expension; (Laboratory ware, cooking utensils Compatible with bone,( Coating on srgical implants

Borosilicate

5% Na2O, 3% CaO, 16% B2O3, 76% SiO2 24% Na2O, 24% CaO, 6% P2O5, 46% SiO2

Bioglass

R.Chang, p 460-462

Type Of Glass

Composition (mass)

Properties & Uses

Pure Quartz Glass

100 % SiO2
60-80% SiO2, 10-25% B2O3, Littke Al2O3

Low thermal expansion, Transparent (Optical research)

Low thermal expansion, Transparent ( Lab Ware, House hold ware ) Attck by chemical, Transparent, Sensitive to thermal shock ( Windo glass, Bottles) High Melting, (Cooking ware)

Pyrex Glass

Soda-lime

12% Na2O, 12% CaO, 76% SIO2

Aluminosilicate

5% B2O3, 10% MgO, 10% CaO 20% Al2O3, 55%SiO2 10% Na2O, 20%PbO, 70% SIO2

Lead alkali

High refractive index; (Lenses, Decorative glass) Low Coefficient of thermal expension; (Laboratory ware, cooking utensils Compatible with bone,( Coating on srgical implants

Borosilicate

5% Na2O, 3% CaO, 16% B2O3, 76% SiO2 24% Na2O, 24% CaO, 6% P2O5, 46% SiO2

Bioglass