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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;
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
1 2
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
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 )
--------H reaction AC + B
--------------Reaction Coordinate
Atom at distance
Energy
Atom Bonded In Molecule
Weaker bonded
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
Electropositive element, (Na) gives up one valence electron, to have octet configuration and form a positive charge Na+ = 10
Octet Configuration Stable
Electronegatif element, (F) received one valence electron, to have octet configuration and form a negative charge
10F
Different charge Of (Na+) and (F-) attract together by electrostatic force to form ionic bond
Na+
F-
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
.. .. : F: : F : .. ..
FF Covalent 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
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
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
i)
Common salt
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
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
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
six
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
**
1s 2s 2px 2py 2pz
Excited
How many unpaired electron available for formation bonding now that carbon atom have?
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
= >sp3
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
**
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
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 ?
**
Discuss the formation of hybridization in: i) NH3 ii) H2O iii) BeCl2
In the chemical reaction the covalent bond beak by two ways: i) Homolytic ii) Heterolytic
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 .. ?
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
Example
(Carboanion)
(CH3)3 C :
Cl( anion )
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
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)
Electro mean is related with electron Phile mean loving Loving electron
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
electrophile
G.I Brown, p 56
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
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
190-250
11-14
Fuel Solvent
Gas Fraction
You are given a mixture containing C2H6, C10H22, C40H80. Discuss how the mixture can be saperated ?
Saturated
Unsaturated
Aromatic
Ethers
Ketones
Carboxylic Acids
Aldehydes
amines
Acid
Acid Anhydrides
Acid Halides
esters
Nitriles
amides
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)
100 % SiO2
60-80% SiO2, 10-25% B2O3, Littke Al2O3
Pyrex Glass
Soda-lime
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)
100 % SiO2
60-80% SiO2, 10-25% B2O3, Littke Al2O3
Pyrex Glass
Soda-lime
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)
100 % SiO2
60-80% SiO2, 10-25% B2O3, Littke Al2O3
Pyrex Glass
Soda-lime
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