Chemistry Lecture Notes 2010

Ajman University
Of Science And Technology Network
College Of Pharmacy
And Health Sciences
Notes on:
GENERAL CHEMISTRY COURSE
For Dentistry Students (700126)
2010/2011
1 General Chemistry - Dentistry

General:
 Course Title: General Chemistry
 Course Code:(700126)
 Credit Hours: 3 Credit Hours

 LectureHours: 2 Hrs. (2 C.H.)
 Lab Hours: 2 Hrs. (1 C.H.)
 Pre-requisite: None
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Course Description:
This course includes two major parts:
 Part I: General part will introduce the student
to basic aspects of general chemistry, i.e.:
 atomic structures, electronic configuration,
periodic table of elements, chemistry of metals,
and the fundamentals of chemical bonds and
chemical reactions.
 Part II: Organic part will cover some important

areas in organic chemistry, which include:
 aliphatic and aromatic hydrocarbons,
stereochemistry, as well as some functional
groups, e.g: alcohols, phenols, carbonyl
compounds.
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Course Objectives:
 The course is aimed to:
 provide some fundamental
knowledge of general and organic
chemistry.
 provide the basis of more detailed
understanding of that part of
chemistry specifically related to
living systems and drugs and on
which biochemistry can be built.
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Learning and
Information Resources:
Student's Textbook:
 Masterton, Hurley: "Chemistry,
Principles and Reactions“
Publisher: Saunders Golden Sunburst
Series, Saunders College Publishing
USA, ISBN: 0-03-005889-9
Further Readings:
 Hart, Craine and Hart: "Organic
Chemistry, A short Course"
Publisher: Houghton Mifflin Company,
Boston Toronto ISBN 0-395-70838-9
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5
Other References:
Computer Software:
 General Chemistry Interactive CD-ROM, Ver 3.0
Interactive CD
Recommended Web-Sites:
 http://www.lib.utexas.edu/Libs/Chem/
 http://www.learnchem.net/tutorials/basc.shtml
 http://www.webelements.com/
 http://homework.chem.uic.edu/IEMDL.HTM
 http://www.acdlabs.com/iupac/nomenclature/
 http://www.chemhelper.com/tutorials.html
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Assessment
Of The Students:
 The evaluation is based on students’
performance in written examinations,
quizzes and practical skills.
 The 100 Marks are distributed as
follows:
 20 Marks for Quizzes
 20 Marks for Mid-Term Examination
 20 Marks for Practical Examination, and
 40 Marks for Final Examination
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PART – I:
Introduction

Introduction:
(Ref.: Textbook, pp 2)
 What is chemistry?
 What is matter?
 Matter: is anything that has mass and
occupies space
 Classification of matter:
Matter
Mixtures Pure substances
heterogeneous homogeneous Elements Compounds

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ionic molecular

Introduction:
 Elements:
 An element: is a type of matter that cannot be
broken down into two or more pure substances
 Symbols of elements
Periodic Table
of Elements
 Compounds:
 A compound: is a pure substance that contains
more than one element.
 Fixedcomposition of elements
 Methods of separation:
• Heat
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• Electrolysis

Introduction:
Mixtures:
 A mixture: is a type of matter that contains two or more
substances combined in such a way that each substance
retains its chemical identity.
 Types of mixtures:
• Homogeneous mixtures (uniform)
• Heterogeneous mixtures (nonuniform)
 Methods of separation:
• Filtration See Description on
• Distillation screen 1.7 in
• Crystallization Interactive CD
• Extraction
• Chromatography
Problems:
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-Compare between compounds and mixtures.

Interactive CD
-Solve exercise on screen 1.6 in

Properties of Substances:
 Identification of substances
 Intensive versus extensive properties
 Chemical properties
 Physical properties:
• m.p. & b.p.
• Density
• Solubility
Problems:
- Textbook pages 21-25
- Solve exercises and tutorials on screens 1.12
and 1.15 in Interactive CD
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Atoms, molecules and ions

Atoms, Molecules and Ions:
 Atoms:
 Atomic structure:
(Source: interactive CD, screen 2.4)

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 Dalton’s Atomic Theory:

 An element is a substance that cannot be broken
down by chemical means. Elements consist of
atoms.
 All the atoms in a particular element behave in
the same way chemically, and they share the
same ATOMIC NUMBER.
 In ordinary chemical reactions atoms cannot be
disappeared or changed to another atoms of
another elements.
 Elements combine chemically to form substances
called COMPOUNDS.
 The ATOM is the smallest particle of an element
that can enter into a chemical reaction.
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See screen 2.5 on

Interactive CD
 Atoms:
 Components of the atom: (Rutherford
Hypothesis)
• Electrons
• Atomic Nucleus: protons and neutrons
 Atomic Number (Z)
 Atomic Mass (A) See Summary on
 Nuclear symbol screen 2.9 in
 Isotopes: Interactive CD
• Isotopes in medicine (see Textbook, page 510)
Problems:
- Search for the radioactive isotope(s) used in dental
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radiology
- Further questions

 Molecules:
 Definition
 Chemical bonds:
• Ionic chemical bonds
• Covalent chemical bonds
 Presentation of molecules: examples
• Molecular formulas
• Expanded structural formulas
• Condensed structural formulas
• Ball and stick molecular models
• Space filling molecular models
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Problems:
Solve exercises and tutorials on screens 2.15 in Interactive CD

 Ions:
 Definition
 Ionization
 Classification of ions:
ions
Monatomic Polyatomic
(charged atoms) (charged molecules)
cations anions cations anions

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Problems:
Solve tutorials on screens 2.16 in Interactive CD
 Ionic compounds:
 Definition
 Ionic
bonds
 Formulas of ionic compounds:
• Electrical neutrality
• Ions with and without Noble-Gas Periodic Table
Configurations of Elements
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 Nomenclature of compounds:
 Naming cations:
• Monatomic
• Polyatomic
 Naming anions:
• Monatomic
• Polyatomic
• acids
 Naming ionic compounds
 Naming molecular compounds
 Naming hydrates
Problems:
- Textbook pages 47-51
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- Solve tutorials on screens 2.17 -2.19 in Interactive CD

- Online tutorial:
http:gemini.tntech.edu/~snorthrup/chem111/tutorials/chap4c/prob1q.html
Electronic structure
and periodic table of
elements

Electron configurations:
 Atomic structure:
 Shells / Energy levels
 Quantum Numbers
 Atomic orbitals:
 Shapes of Atomic Orbitals (examples)
 Electron configuration:
 Definition
 Pauli’s Exclusion Principle
 Filling of Atomic Orbitals
 Hund’s Rule
Problems:
- Solve tutorials on screens 6.12, 6.13, 6.15 in Interactive CD
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- See online gallery of atomic orbitals at:

http://www.shef.ac.uk/chemistry/orbitron/

Periodic Table of Elements:
 Classification of Elements, according to:

 Metallic and nonmetallic
 Acidic and basic
 Valency
 Atomic weight and atomic number
 Periodic System
 Metals, nonmetals and metalloids
(See interactive CD, Tools: Periodic Table)

Interactive CD
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Periodic Table of Elements:
 Electron configuration and the Periodic Table

 Trends in the Periodic Table:
 Atomic number and atomic radius
 Ionization Energy
 Electron Affinity
 Electronegativity:
• Electronegativity and types of chemical bonds
 Lewis Electron Dot Diagram (See interactive
CD, screen 7.4)
Problems:
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- Textbook pages 156, 158 pp
- Solve tutorials on screens 6.17 -6.19 in Interactive CD

Hybridization:
 Hybrid Orbitals: (examples)

 sp-Hybridization
 sp2-Hybridization
 sp3-Hybridization
 sigma (σ) bonds:
 s,s- sigma (σ) bonds
 s,px- sigma (σ) bonds
 px,px- sigma (σ) bonds
 pi (π) bonds:
 py,py-pi (π) bonds
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 pz,pz-pi (π) bonds

Solutions

Reactions in aqueous solutions:
Aqueous Solutions:
Solutes and solvents
Saturated, concentrated and diluted solutions
Methods used to express relative amount of

solute and solvent in solution. These methods
include:
(1) Mass percent g %:

A solution can be prepared to specify, the
mass of solute in gram dissolved in 100 ml of
a solvent.
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Example:
 An isotonic solution is prepared to contain both 0.9 % of
sodium chloride (NaCl) and 5% glucose (C6H12O6) in water.
Calculate the mass of NaCl and C6H12O6 dissolved to
prepare 500 mL.
Solution:
A)0.9 % Sodium chloride means 0.9 grams per 100 mL so,
to prepare 500 mL, the amount needed is:
0.9 X 500/100 = 4.5 g
B)5 % Glucose means 5 grams per 100 mL so, to prepare
500 mL the amount needed is :
5 X 500/100 = 25 g
 Weigh 4.5 g of powdered NaCl and 25 g powdered
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glucose dissolve in sufficient amount of water, then

complete to 500 mL of the same solvent.
(2) Molarity (M):
Molarity is the number of moles of solute per
liter of solution. Unit: M=moles/L
molarity (M)= moles of solute
liters of solution
Mole: is a collection of 6.0122x1023 items.
The mass in grams of one mole of a substance
is numerically equal to its formula mass
(molecular weight).
1 Molar solution is prepared by dissolving
one gram molecular weight (Mole) of any
solute in 1 liter of solvent.
Molecular weight is the summation of atomic
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weights of the solute.

Example:
 To prepare 1 mole of NaCl ( Na =23 and Cl =
35.5), 58.5 grams of NaCl dissolved in 1 liter
Problems:
Show how you can prepare the following
solutions
1. 0.1 M HCl from concentrated HCl (35%)
2. 0.5 M copper(II) sulphate solution.
3. 2 M glucose solution (C6H12O6)
4. 0.5 M of acetic acid solution from 10 % acetic

acid solution (CH3COOH).
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5. Further Problems: see Textbook pp 95, and

interactive CD.
Problems:
Express the concentration of the
following solution by M and g %:
1. 10 ml of 10 % acetic acid solution was
diluted up to 500 mL with distilled
water.
2. 5 grams of copper(II) sulphate penta
hydrate in 1 liter distilled water
3. 10.8 grams of glucose in 100 mL
distilled water
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Chemistry of metals

Chemistry of metals:
 Metals: are group of elements that share
certain properties:
 They conduct heat and electricity well, and
 They can be shaped easily.
 88% of elements are metals
 Physical properties of metals: (used to
differentiate metals from nonmetals):
 Solids with high m.p. and b.p. (except Hg)
 High density
 Good conductors
 Shiny
 Malleable and ductile
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 Formation of mixtures (alloys)

Chemistry of metals:
 Classification of metals:
 Main-group metals: (s-block metals)
• Alkali metals (Group 1)
• Alkaline earth metals (Group 2)
 Transition metals:
• d-block metals
• f-block metals (Lanthanides and
Actinides)
 p-block metals
 metalloids
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Reactions of metals:
Reactions of alkali and alkaline earth
metals:
 Alkali and alkaline earth metals are the
most reactive of all elements. (why?)
 Reaction with Hydrogen
 Reaction with nonmetals: (S, X , O , N )

2 2 2
 Reaction with water
Problems:
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- Textbook pages 548 pp

Redox Reactions of transition metals:
 Oxidation and reduction
 Oxidizing agents and reducing agents
 Oxidation number
 Calculation of oxidation number (page

89)
 Balancing Redox Equations (pages 90-
91)
(See Examples)
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Precipitation Reactions:
 Precipitation reaction is the reaction which
involves the formation of precipitates.
 A precipitate (ppt) is a substance which
separates as a solid phase out of the
solution.
 Solubility is the molar concentration of the
saturated solution. It depends on:
 Temperature
 Pressure
 Concentration of other solutes
 Composition of the solvent
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 Practical uses of precipitation reactions

Complexation Reactions:
 Complexation reaction is the reaction which
leads to the formation of complex ions.
 A complex ion is an ion containing a central
metal atom bonded to two or more ligands.
 Coordinate covalent bonds and coordination
number
 Charges of complexes
 Chelating Agents.
Assignment:
Search for the medical uses of chelating agents in
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-
Dentistry (Oral Chelating Therapy)

Acid-Base Reactions:
Definitions of acids and bases:
 Arrhenius Definition
 Limitation of Arrhenius definition
 Lowry-Brønsted Definition (page: 351)
 Lewis Definition: (page: 404)
 Strong and weak acids and bases
 Conjugate acids and bases
 Amphiprotic solvents
 Monobasic and poly basic acids
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pH Scale:
 The acidity or basicity (alkalinity) of a solution
can be described in terms of its hydrogen ion
[H+] concentration.
 It is defined by using the pH notation:
pH= -log10 [H+]

Or
[H+] = 10 -pH
 Most aqueous solutions have hydrogen ion

concentrations between 1-10-14 M, and hence
have pH between 0-14.
 The pH of a natural solution is 7
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 If the pH <7, the solution is acidic

 If the pH >7, the solution is basic (alkaline)
 Relationship between pH and [H+]:
pH 0 1 2 3 4 5 6 7 8 9 10 11 12 13 14
acidic alkaline
[+H] 1 10-1 10-2 10-3 10-4 10-5 10-6 10-7 10-8 10-9 10-10 10-11 10-12 10-13 10-14
See Further Problems:

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Ionization of water:
+ -
H2O H + OH
 In any solution: pH+pOH = pKw
 Kw is known as the Ion product constant of
water
 Kw = [H+] [OH-]
 At 25oC, Kw=1.0x10-14
+ -
In pure water: [H ] = [OH ]
... K w = [H+]2

+ -7 -1
[H ] = K w = 10 mol lit
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 Since water is neutral,
a solution whose [H+] > 10-7 is acidic,
whereas a solution whose [H+] < 10-7 is alkaline.
Buffer Solutions: (page 379)

 Buffer solution is a solution that resists changes in pH upon
addition of small amounts of acids or bases.
 A buffer solution consists of a weak acid and its conjugate
base (e.g: CH3COOH and CH3COONa) or a weak base with
its conjugate acid (e.g.: NH3 and NH4Cl)
 The buffer action can be explained by the neutralization of
the added acid by the base present in the buffer solution,
and the neutralization of the added base by the acid
present in the buffer solution.
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Assignment:
- Search for the medical uses of buffer solutions
PART – II:
Organic Chemistry

Introduction:
 What is Organic Chemistry?
 Uniqueness of carbon:
 Carbon ranks only twelfth (12th) in abundance among the
elements.
 Carbon constitutes less than 0.1% of the earth's crust,
oceans and atmosphere.
 Structure of carbon atom
 Carbon in periodic table in Group IVA
 Carbon atom in tetravalent
 Carbon must form Four Bonds to satisfy its octet of
electrons
 Bonds may be with other carbons or with other elements
See interactive CD #2: Screen 22.2
Types of carbon compounds
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 Hybridization of carbon
Hydrocarbons:
 Definition
 Classification:
)Hydrocarbons (HC
aliphatic HC Aromatic HC
Saturated HC Unsaturated HC homocyclic heterocyclic
alkanes alkenes alkynes

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See interactive CD #2: Screen 22.3

Saturated Hydrocarbons

Saturated Hydrocarbons (Alkanes):
 Structure of alkanes:
 sp3 hybridization
 tetrahedral structures:
methane ethane propane
 General formula: CnH2n+2

 Classification:
 Open-chain: straight and branched chains
 Cycloalkanes
 homologous series
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 Isomeric structure of alkanes:
 Isomers: are different compounds with
identical molecular formulas.
 Isomers are readily distinguishable from each
other because they exhibit differences in their
physical and chemical properties.
 The first three members of alkane series have
no isomers, because there is only one way in
which the carbon atoms can join together.
 All the higher alkanes have isomers.
 Nomenclature of alkanes: (Textbook page: 617)
 Common Nomenclature
 IUPAC Nomenclature (International Union of Pure
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and Applied Chemistry )

 The IUPAC system of nomenclature follows the rules
indicated below:
1. Select as the parent structure the longest
continuous chain.
2. Number the parent carbon chain starting from
whichever end will give the lowest number for the
point of attachment of the substituent.
3. If the same alkyl substituent occurs more than
once on the parent carbon chain, the prefixes di-,
tri-, tetra-, penta- etc.. are used to indicate
whether there are two, three, four or five
substituents.
4. If several different substituents are attached on the
parent carbon chain, they are named either in order
of increasing complexity or in alphabetical order.
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Problems:
 Give the IUPAC name for each of the following compounds:
CH3
a) CH3 CH CH2 CH2 CH3 b) CH3 C CH2 CH CH2 CH3
CH3 CH3 CH2
CH2
CH3
CH3 NO2 NH2

c) CH3 CH2 CH2 CH CH2 C CH2 CH3 d) CH3 CH CH CH CH2 CH3
CH CH3 CH2 NO2
CH3 CH3
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Problems:
 Write the structural formula of a compound whose
IUPAC name is:
a) 2,2,5-Trimethyl-4-ethyl heptane
b) 2-Bromo-3-chloro-4-isoprpyl octane
 The following IUPAC names are incorrect, write the

structural formula and correct the names:
a) 3,3-diethylbutane
b) 2-Ethyl-3-bromo butane
c) 3-Chloro-2-bromo pentane
 Draw all possible structures of the following general
formulas:
a) C4H9Cl
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b) C5H11 Cl

Cycloalkanes:
 Cycloalkanes are alkanes that exist in the form of a ring
 Nomenclature of cycloalkanes:
 Cycloalkanes are also called:
• cyclic aliphatic hydrocarbons, or
• alicyclics
 Cycloalkanes are named by simply attaching the prefix
(cyclo-) to the name of the open chain hydrocarbon that has
the same number of carbon atoms as in the ring:
H H CH2
C
H H CH2 CH2
C C
H H
Cyclopropane
H H
H C C H H2C CH2
H C C H H2C CH2
H H
Cyclobutane
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H H
H C CH2
H H2C CH2
C C
H H
H C C H H2C C H2
H H
53 Cyclopentane
General Chemistry - Dentistry
Cycloalkanes:
Problems:
1. The general formula for an alkane is CnH2n+2. What
is the corresponding formula for a cycloalkane with
one ring?
2. Draw the structural formulas for:
• 1,3-dimethylcyclohexane
• 1,2,3-trichlorocyclopropane
1. Give IUPAC names for:
Cl
a) Br
b)
Br
Br
CH3 Br
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c) CH CH CH CH2 Br
CH3

Physical Properties of Alkanes:
1) Occurrence:
 At room temperature alkanes occur as gases,
liquids and solids:
 C1-C4 (methane to butane) are gases
 C5-C17 (pentane to heptadecane) are liquids
 C18 and larger alkanes are solid waxes
2) Solubility:
 Alkanes are nonpolar compounds
 Their solubility characteristic may be predicted by
"like-dissolves-like" rule.
 This means:
Nonpolar compounds are soluble in other nonpolar
solvents and polar compounds are generally soluble
in other polar solvents.
Thus, alkanes are soluble in the non-polar solvents

carbon tetrachloride, CCl4, and benzene C6H6, but they
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are insoluble in polar solvents such as water, H2O.

Physical Properties of Alkanes:
3) Boiling points:
 Generally the boiling point of n-hydrocarbon
increases with increasing molecular weight.
 20-300C for each addition of carbon atom:
400
300
200
boiling points
100
0
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19
(oC
-100
)
-200
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number of carbon atoms in n-alkanes

Reactions of Alkanes:
 Alkanes are also called Paraffin hydrocarbons
(from the Latin: parum=little; affinis=affinity)
because of their lack of reactivity.
 Two important reactions that alkanes do undergo,
however, are combustion and substitution.
1) COMBUSTION OF ALKANES: (OXIDATION)

 Alkanes combine with oxygen to form:
 Carbon dioxide (CO2), water (H2O), and a large
quantity of heat (the heat of combustion):
3n+1
CnH2n+2 + 2 O2 n CO2 + (n+1)H2O + HEAT
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2) SUBSTITUTION REACTIONS OF ALKANES:
 Halogenation:
R H + X2 heat or R X + HX
U.V. light
Alkane Halogen Alkyl
halide
 Examples:
U.V.
a) CH4 + Cl2 CH3 Cl + HCl
U.V.
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b) CH3 CH3 + Cl2 CH3 CH2 Cl + HCl

MECHANISM OF SUBSTITUTION REACTIONS
OF ALKANES:
U.V.
a) CH4 + Cl2 CH3 Cl + HCl
U.V.
b) CH3 CH3 + Cl2 CH3 CH2 Cl + HCl
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 Orientation of Substitution
CH3CH2CH2Cl
X n-propyl chloride
U.V.
a) CH3CH2CH3 + Cl2
- HCl
propane CH3 CH CH3
Cl
isopropyl chloride
 Ease of substitution of a hydrogen atom follows this

sequence:
3oH > 2oH > 1oH
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Ease of hydrogen substitution increases

Problem:
 Draw the structures and give the IUPAC names of
all possible monochloro and dichloro derivatives
of:
 n-butane
 Isobutane
 n-pentane
 Isopentane
 Neopentane
 Determine the main products obtained by the

chlorination reactions mentioned above
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Unsaturated Hydrocarbons

Unsaturated Hydrocarbons (Alkenes):
 Alkenes are characterized by the carbon-carbon
double bond.
 Structure of alkenes:
 sp2 hybridization
 Trigonal planar structure:
o
120
 General formula: CnH2n

 Structure of ethylene:
π-bond
H H
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C C
H σ-bond
H
 Nomenclature of alkenes:
 Common Nomenclature
 IUPAC Nomenclature
 Rules of IUPAC Nomenclature:

1. The longest continuos carbon chain containing the
double bond is selected as the parent chain.
2. The name of the parent carbon chain is obtained by
replacing the ending (-ane) of the corresponding
alkane by the suffix (-ene).
3. The parent chain is numbered so that the double
bond is assigned the lowest number.
4. The position of the double bond is assigned the
number of the first double-bonded carbon.
5. The entire compound is named by first listing the
substituents either in alphabetical order or in order
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of complexity.

Problems:
 Give the IUPAC names of the following compounds:
CH3 CH3 H3C
a) CH3 CH C CH CH CH2 CH2 CH3
CH e)
CH3 CH3
NH2
Cl
b) CH3 CH CH2 C CH2 CH3 Cl
CH2 d)
Br
Br
CH3 CH3
c) CH3 C C CH2 CH2 CH CH3
Br
 Write the structural formula for the following compounds:

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 2-Methyl-2-butene
 4,5-Dimethyl-3-isopropyl-2-hexene
 2-Chloro-4-methyl-2-pentene
Geometric Isomerism:
 Geometric isomers are compounds that differ only
in the arrangement of their atoms in space as
result of restricted rotation about a bond:
 cis-configuration:
When alkenes have substituents on the
same side of the double bond.
 trans-configuration:
When alkenes have substituents on
opposite sides of the double bond.
 For cis-trans isomerism in alkenes, each carbon of

the double bond must have two different atoms or
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groups attached to it.

Example:
 1,2-dichloroethene exists in two different forms:
H H H Cl
C C C C
Cl Cl Cl H
cis-1,2-dichloroethene trans-1,2-dichloroethene
o o o o
(b.p 60 C, m.p -80 C) (b.p 47 C, m.p -50 C)
Problem:
 Which of the following compounds can exist as
cis-trans isomers? Draw their structures.
 1-butene
 2-butene
 propene
 3-hexene
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 2-hexene
 2-methyl-2-butene

Physical Properties of Alkenes:
 In general, the physical properties of alkenes
are much the same as those of corresponding
alkanes.
 At room temperature:
 the C2 to C4 alkenes are gases.
 the C5 to C18 alkenes are liquids.
 those above C18 are solids.
 Solubility and boiling points (see alkanes)

 Like alkanes, the alkenes are insoluble in water
and soluble in organic solvents (explain why?)
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Reactions of Alkenes:
(see interactive CD #2: screen 22.4)
ADDITION REACTIONS OF ALKENES
 A reagent (A-B) adds across the double bond to give a
saturated product that contains all atoms of both
reactions:
 General Equation:
C C + A B C C
A B
1. Addition of Hydrogen:
 It is the catalytic hydrogenation of alkenes to give the
corresponding alkanes:
Pt / Ni
+ H2 C C + Heat
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C C or Pd
H H
alkene alkane
2. Addition of Halogen:
 It is the addition of halogens (Chlorine or Bromine) to
an alkene to give an alkyl dihalide.
X
C C + X2 C C (X2= Cl2 or Br2)
X
alkene halogen dihalide
 This reaction is known as the halogenation of alkenes.

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3. Hydroxylation: The Baeyer Test:
 It is the addition of alkaline potassium permanganate,
KMnO4 to an alkene to give a dihydroxy alcohol or
glycol and a brown precipitate of manganese dioxide
MnO2:
[OH-]
C C + KMnO 4 C C + MnO2
OH OH ppt
alkene (purple) a glycol (brown)
 This reaction is used to identify the presence of the

carbon-carbon double bond.
It is called "the Baeyer Test".
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4. Addition of Hydrogen Halide(H-X):
 Alkenes react with hydrogen halides to form alkyl
halides:
C C + H X C C
H X
alkene alkyl halide
 This reaction is known as the hydrohalogenation of

alkenes
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Orientation of hydrohalogenation:
 MARKOVNIKOV'S RULE:
The Markovnikov's Rule states that:

CH 3 CH3
"In ionic addition of H-X to unsymmetrical
CH3 C CH2 + HCl alkenes, CH
the3 Cpositive
CH3
hydrogen of the hydrogen halide adds to the double-bond Cl
carbon that bears the greater number of hydrogen atoms, and
t-butylchloride
isobutylene
the negative halide ion adds to(2-methylpropene)
the double-bond carbon that
(2-chloro-2-methyl-
bears the least number of hydrogen atoms." propane)
and NOT:
CH3 CH3 CH3 CH3

CH3 C CH2 + HCl CH3 C CH3 CH3 C CH2 + HCl CH3 CH CH2 Cl
Cl
isobutylene t-butylchloride isobutylchloride
isobutylene
(2-methylpropene) (2-chloro-2-methyl- (1-chloro-2-methyl-
(2-methylpropene)
propane)
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propane)
and NOT:
73
CH CH3 General Chemistry - Dentistry
3
Unsaturated Hydrocarbons (Alkynes):
 Alkynes are characterized by the carbon-carbon
triple bond.
 Structure of alkynes:
 sp hybridization
 linear structure:
o
180
 General formula: CnH2n-2

 Structure of acetylene:
π bond σ bond
H C C H
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π bond

 Nomenclature of alkynes:
 Common names are used for low-molecular-
weight alkynes, and they named as substituted
acetylenes
 For more complicated alkynes the IUPAC names
are used.
 The IUPAC rules for naming alkynes are similar
to those for alkanes and alkenes.
 The ending (-yne) is used for a triple bond, and
(-diyne) for two triple bonds.
 Compounds with a double and a triple bond are
(-enynes), the double bond receives the lowest
numbers.
 Numbers as low as possible are given to double
and triple bonds, even though this may at times
give (-yne) a lower number than (-ene).
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 When there is a choice in numbering, the double

bonds are given the lowest numbers.
 Nomenclature of alkynes:
 Examples:
5 4 3 2 1 1 2 3 4 5 6
a) CH3 CH C C CH3 b) CH C CH CH2 C CH
Br CH3
4-Bromo-2-pentyne 3-Methyl-1,5-hexadiyne
1 2 3 4 5 4 3 2 1
c) CH2 CH C CH d) CH3 CH CH C CH
1-Buten-3-yne 3-Penten-1-yne
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Problem:
 Give the IUPAC name of the following
compounds:
Cl CH3
a) CH3 CH CH C C CH2 CH CH2 CH3
CH3
b) CH2 C C CH
CH3
Br
c)
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Physical Properties of Alkynes:
 In general, the physical properties of alkynes
are much the same as those of corresponding
alkanes and alkenes.
 At room temperature:
 the C2 to C4 alkynes are gases.
 the C6 to C18 alkynes are liquids.
 those above C18 are solids.
 Solubility and boiling points (see alkanes and

alkenes)
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Reactions of Alkynes:
ADDITION REACTIONS OF ALKYNES
1. Addition of Hydrogen:
 Alkynes add hydrogen in the presence of catalysts (Pt,
Ni or Pd) to form the corresponding alkanes:
H H
+ H2 + H2
C C C C C C
Pd or Ni H H Pd or Ni
H H
alkyne alkane
 This reaction is called catalytic hydrogenation of

alkynes.
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Reactions of Alkynes:
2. Addition of Halogen:
 Alkynes react with two molecules of halogen to give
tetrahalides:
X X
+ X2
C C + X2 C C C C
X X X X
3. Addition of Hydrogen Halide: Hydrohalogenation of

alkynes: C C + HX C C
 The addition of hydrogen chloride,H X bromide or iodide to
alkyne the Markovnikov's
alkynes follows Rule.
haloalkene
H X
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HX+
C C + HX C C C + HX C C
H X
H X H X
alkyne haloalkene a gem-dihalide
Nomenclature of Further
Functional Groups in Organic
Chemistry
A functional group is a specific group of

atoms responsible for the characteristic
reactions of a compound.
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Chemical Functional Group Examples Common Names IUPAC Names
Group
Alcohols Methyl alcohol Methanol
CH3 O H
Ethyl alcohol Ethanol

CH3 C H2 OH
n-Propyl alcohol 1-Propanol

C OH CH3 CH2 CH2 OH
CH3 CH OH Isopropyl alcohol 2-Propanol
CH3
Cyclohexyl alcohol Cyclohexanol
OH
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Group
Aldehydes H Formaldehyde Methanal
H C O
Aldehyde Acetaldehyde Ethanal
(carbonyl): H
H CH3 C O
C O Propionaldehyde Propanal
H
CH3 CH2 C O
Ketones Dimethyl ketone Propanone

CH3 (Acetone)
CH3 C O
Methyl n-propyl ketone 2-Pentanone
Keto (carbonyl): CH3
CH3 C H2 CH2 C O
C O
Cyclohexyl ketone Cyclohexanone
O
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Group
Carboxylic OH Formic acid Methanoic acid

Acids:
H C O
Carboxyl:
OH Acetic acid Ethanoic acid
OH CH3 C O
C O
OH Propionic acid Propanoic acid
CH3 CH2 C O
Esters: Methyl acetate Methyl ethanoate
O
Ester: CH3 C O CH3
O O Methyl propionate Methyl propanoate
C O R CH3 CH2 C O CH3
Ethers: Dimethyl ether Methoxymethane

Ether (Alkoxy): CH3 O CH3
Methyl ethyl ether Methoxyethane

C O C CH3 CH2 O CH3
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Diethyl ether Ethoxyethane

CH3 CH2 O CH2 C H3

Group
Amines: Ethyl amine Ethanamine

CH3 CH2 N H2
(1o a mine)
Amino:
H Dimethyl amine N-Methyl methanamine
CH3 N CH3
(2oa mine)
N
CH3 Dimethyl ethyl amine N,N-Dimethylethanamine
CH3 CH2 N CH3

(3oa mine)
Amides: Acetamide Ethanamide

O
Carboxamide: CH3 C NH2
O
N-Methyl acetamide Methyl ethanamide
C N O
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CH3 C NH C H3

I) Name the following compounds:
(1) (2) (3)
Cl
O
OH
CH3 C H C CH2 C H3
CH2 C CH2 C H CH3
CH2 C H3
OH Br
NO 2 CH2 CH3
(4) (5) (6)
CH2 C H3
CH3 C H O CH3
NH2 O CH3 C C OOH
CH3
CH3 C H CH C H2 C H NH2
CH3
(7) (8) (9)
O
Cl Cl
CH3 CH C CH3 O
CH3 C H C CH2 O H
CH C NH C H3
CH3 CH3
(10) (11) (12)
O O
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O
CH3 C NH CH3 C H C O CH2 CH3
C O CH3
CH3

II) Draw structures of the following compounds:
(1) 2,5-diamino cyclopentanone (2) N,N-dimethyl benzamide

(3) Ethyl butanoate (4) Cyclobutyl acetaldehyde
(5) diisopropyl ether (6) Nitro acetate
(7) Cyclopentyl methyl ketone (8)3-bromo-4-chloro-5-nitro-2-hexanol
(9) Triethyl amine (10) 2-amino-4-methyl-pentanoic acid

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Aromatic Hydrocarbons

Aromatic Hydrocarbons:
 The term aromatic was originally used to
designate compounds with spicy or sweet
smelling odours derived from plants.
 A compound is said to be aromatic, if it is
benzenelike in its properties
Structure of Benzene: (Kekule's Proposal)
 F.A. Kekule's proposed in 1865 a structure for
benzene:
 Benzene consists of a cyclic, hexagonal, planar
structure of six carbon atoms with alternating single
and double bonds: H
H C H
C C
C C
H C H
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benzene (1,3,5-cyclohexatriene)
The Kekule's structure
Aromatic Hydrocarbons:
Structure of Benzene: Theory of Resonance
( The modern proposal )
The Resonance Theory:

This theory may be stated as follows:
1. Whenever a molecule can be represented by two or

more equivalent structures that differ only in the
arrangement of electrons, there is resonance. The
actual structure of the molecule is a hybrid that
combines the characteristics of all these structures.
The individual structures are called contributing
structures and do not exist independently.
2. The resonance hybrid is more stable (contains
less internal energy) than any of the contributing
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structures. This increase in stability is referred to

as resonance energy.
Nomenclature of Aromatic Compounds:
A) Monosubstituted Benzenes:
 Because all six positions in benzene are
equivalent there is no need to specify by a
number the position of a substituent for
monosubstituted benzenes.
 Monosubstited benzenes can be named by
placing the name of the substituent in front of
the word : "benzene":
CH3
Cl CH2CH3 CH3 C CH3 NO2
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chlorobenzene ethylbenzene t-butylbenzene nitrobenzene

A) Monosubstituted Benzenes:
 Some monosubstituted benzenes are
considered parent compounds because they
occur so frequently:
H O
CH3 CH CH2 OH C
styrene phenol benzaldehyde

toluene
COOH NH2 SO3H

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benzoic acid aniline benzene sulfonic acid

B) Disubstituted Benzenes:
 There are three possible isomers of disubstituted
benzenes which are differentiated by the use of
the prefixes ortho (o-), meta (m-) and para (p-) :
 Note that when the two substituents are different,
they are listed in alphabetical order:
Br Br
Br
Br
Br
Br
o-dibromobenzene m-dibromobenzene p-dibromobenzene
C 2H5 F
NO2
Cl
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NO2
I
m-dinitrobenzene o-chloroethylbenzene p-fluoroiodobenzene
B) Disubstituted Benzenes:
 If one of the substituent is part of a parent
compound, then the disubstituted benzene is named
as a derivative of the parent compound:
CH3 NO2
OH
Cl
Br
COOH
o-chlorophenol m-bromotoluene p-nitrobenzoic acid
 Like mono substituted benzenes, certain

disubstituted benzenes are referred to by their
common names CH3
CH3 CH3
CH3
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CH3
CH3
o-xylene m-xylene p-xylene
Problems:
(1) Name the following compounds:
CH CH2 NO2 C 2H5
b) c) d)
a)
F CH3 HO
F Cl
CH3 CH CH CH3 CH2 Cl C CH

Cl
e) f) g) h)
CH2Br O2N
(2) Draw the structures of the following compounds:

a) 2-Phenyl pentane
b) p-Nitroethyl benzene
c) o-Ethyl aniline
d) m-Bromobenzene sulfonic acid
e) 2,2-Dimethyl-1-phenyl butane
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f) m-Nitrobenzoic acid
g) p-bromotoluene
95 h) m-chloro benzaldehyde General Chemistry - Dentistry
C) Polysubstituted Benzenes:
 Polysubstituted benzenes contain three or more
substituents.
 In polysubstituted benzenes the ring must be
numbered and the position of the substituents must
be specified by numbers.
 The numbering starts with one substituent and
continues around the ring so as to use the lowest
possible numbers for the other substituents.
OH C H3
Cl 1
Br 6
1
Br O 2N 6 NO 2
Cl 1
2
Cl 2 2
3
5 3 5 3
6 4 4
4
5
Br NO 2
1,2,3-trichloro- 2,4,6-tribromo- 2,4,6-trinitro-

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benzene phenol toluene

Reactions of Aromatic Compounds:
 Aromatic compounds are stable molecules.
 The stability is attributed to their resonance energy,
which due to the extensive delocalization of the π
electrons in the ring.
 Benzenes and aromatic compounds in general tend
to undergo substitution rather than addition reactions
in order to preserve the delocalized π system.
 Because the aromatic ring is extremely stable, a
highly reactive agent is required to react with the
benzene ring.
 The aromatic ring is also an electron-rich system.
 Attack on the ring takes place by means of electron-
deficient agent, an Electrophile (E+).
The role of catalyst in electrophilic aromatic substitution:

 In almost all electrophilic aromatic substitution a catalyst is
needed for a reaction to take place.
 The catalysts are usually Lewis acids or a protonic acid.
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 The role of these catalysts is to generate powerful

electrophiles.

 General equation: E
+ - catalyst
+ E B + H-B
 Examples of substitutions of benzenes:

1. Halogenation: Br
FeBr3
+ Br2 + H Br
Cl
FeCl3
+ Cl2 + H Cl
2. Alkylation (Friedel-Crafts Alkylation):

R
AlCl3
+ R Cl
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+ H Cl
alkyl alkyl
chloride benzene
 Examples of substitutions of benzenes:
3. Acylation (Friedel-Crafts Acylation):
O
C R
O
+ R C Cl + HCl
acyl chloride alkyl phenyl

ketone
4. Nitration:
NO2
H2SO4
+ HNO3 + H2O
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Other Reactions Of Aromatic Compounds:
1. Halogenation of the alkyl side chain:
CH3 CH2 Br
+ Br2 + HBr
sun-light
toluene benzylbromide
2. Conversion of the alkyl side chain into carboxyl group

(COOH):
Reaction of alkylbenzenes with hot potassium permanganate,
a strong oxidizing agent, forms benzoic acid: (Regardless of
the length of alkyl chain):
CH3 COOH CH3 COOH
a) hot KMnO4 c) hot KMnO4

+ H2O + 2 H2O
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toluene benzoic acid CH3 COOH

p-xylene terephthalic acid
Other Reactions Of Aromatic Compounds:
3. Conversion of Nitro compounds to amines:
Aromatic nitro compounds can be converted to
aromatic amines by treatment with (Fe) and (HCl):
NO2 NH2
Fe, HCl
nitrobenzene aniline
Problems:
 Starting from benzene show how can you prepare the

following aromatic compounds:
1. Benzyl chloride
2. Benzoic acid
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3. Aniline
4. Cyclohexyl benzene

Stereochemistry

Stereoisomerism
 Stereochemistry is a branch of chemistry that deals
with description of the spatial arrangements of atoms
in molecules and with the consequences of molecular
shape of the physical and chemical properties of
molecules.
 It is also defined as:

 The study of the three-dimensional orientations of
the atoms in molecules as they undergo a
chemical reaction.
 Stereoisomerism: is one aspect of Stereochemistry.
 Isomers are compounds that have the same

molecular formula, but are not identical.
 There are two main classes of isomers:

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a) Structural isomers (or constitutional isomers)

b) Stereoisomers
Stereoisomerism
 There are two main classes of isomers:
 Structural isomers (or constitutional isomers)

 Stereoisomers
Isomers
Structural Isomers Stereoisomers
Geometric Optical
(cis - trans) Isomers
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Stereoisomerism
a) Structural Isomers:
 are compounds that have the same molecular formulas
but different structural formulas.
b) Stereoisomers:
 are compounds that have not only the same molecular
formulas but also identical sequence of bonding of the
atoms in the molecule.
 They differ in one respect only:
 the spatial orientation or configuration of their
constituent atoms.
Types of Stereoisomerism:
1. Geometric isomerism:
 The restricted rotation about the carbon-carbon double
bond and the resulting planar geometry is responsible
for geometric isomerism.
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1. Optical isomerism:
 It manifests itself by its effect on plane-polarized light.
Optical Activity
 Optical isomers are optical active substances.
 An optical active substance is any compound that has the
ability to change the direction of plane-polarized light or to
rotate it.
 The rotation itself is called Optical Activity.
Measurement of optical activity

 Optical activity can be measured by placing a solution of the
compound suspected of being optically active in front of the
plane-polarized light and seeing what happens to the light
transmitted by the solution.
 Polarimeters are used to measure the optical activities of
substances.
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Optical Activity
 Plane-polarized light passing through an optically
active solution is rotated by a certain number of
degrees alpha (α ) called the observed rotation.
 If the observed rotation found to be to the right
(clockwise rotation), the optically active compound
is designated as dextrorotatory with the symbol (+):
 If the optically active compound rotates plane-
polarized light to the left (counter clockwise
rotation) is termed levorotatory, with the symbol (-)
Example:
 2-chlorobutane has two optical isomers:
1. (+) 2-chlorobutane: this isomer rotates plane-polarized
light to the right (clockwise), and
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2. (-) 2-chlorobutane: It rotates plane-polarized light to the

left (counter clockwise)

Optical Activity
 The observed rotation (α ) depends upon:
1. The concentration of the solution (c)
2. the length of the polarimeter tube (l)
3. the temperature (T)
4. the wavelength of the light (λ )
Example: observed rotation of (+)-2-butanol:
Concentration Polarimeter tube α

1) 2.0 g/ml 10 cm +27.8o
2) 2.0 g/ml 5 cm +13.9o
3) 4.0 g/ml 10 cm +55.6o
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Optical Activity
 Specific Rotation
 The value of the optical rotation of a compound under
standard conditions is called the specific rotation [α ] , and is
defined by the equation:
T= α
[ α]
λ l x c
Where:
 [α ]=Specific rotation (in degrees)
 T=Temperature (in 0C)
 λ =Wavelength of light*) used (in nm**), usually sodium D-
line 589 nm)
 α=Experimental observed rotation (in degrees)
 l=Length of polarimeter tube (in dm, decimeters: 1 dm = 10
cm)
 c=Concentration of the solution (in g/ml)
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*) Wavelength is the linear distance between successive

maximum or minimum of a wave
**) nm (nanometer) = 10 -9 m
Optical Activity
Problems:
1. Calculate the specific rotation for a solution of 2.0
g/ml of (+)-2-butanol in a 10 cm polarimeter tube
and the observed rotation was +27.800
2. Calculate the specific rotation of cholesterol if the
concentration of the solution is 5.20 g/ml per 100
ml, the length of the polarimeter tube is 5 cm and
the observed rotation was -2.500
3. Search the following web site in the internet for
further problems:
http://www.chem.uic.edu/web1/OCOL-
O. Attef 2008
II/WIN/STEREO/31/FRAMES.HTM

Optical Activity and
Structure of Compounds
 We can predict whether or not a compound will be
optically active based on its structure.
 In order to exhibit optical activity, a compound must
be chiral, that is, it cannot be superimposed on its
mirror image.
Example:
 The mirror image (the "left" hand is not
superimposable of the "right" hand):
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 Compounds that are mirror images of each other
and are not superimposable, are called
enantiomers. (from Greek: Enantio = opposite,
Meros = part)
 Enantiomers are optical isomers. They have the
same properties except that they rotate plane-
polarized light in opposite directions (but in equal
amounts)
mirror
CH3 CH3
H C * *C H
CH3CH2 Cl Cl CH2CH3
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the two optical isomers (enantiomers)

of 2-chlorobutane
 Chiral compounds have a chiral center, which is an
atom (usually carbon, called: stereogenic carbon
atom) bonded to four different atoms or groups.
 The chiral center is usually indicated by an

asterisk(*)
 Compounds without chiral center are called achiral

(not chiral).
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Problems
1. The formulas for a series of compounds are given below.
Indicate the chiral carbon(s) in each molecule with an asterisk
(*):
A) 1-chloropentane
B) 2-chloropentane
C) 3-chloropentane
D) 1-chloro-2-methyl pentane
E) 2-chloro-2-methyl pentane
F) 3-chloro-2-methyl pentane
G) 4-chloro-2-2methyl pentane
H) 1-chloro-2-bromo butane
I) (Amphetamine)
CH2 CH CH3
NH2
J) (Penicillamine)
CH3
CH3 C CH COOH
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SH NH2
2. Search the following web site in the internet for further problems:
http://www.chem.uic.edu/web1/OCOL-
II/WIN/STEREO/21/FRAMES.HTM

Racemic Mixture
o When enantiomers are mixed together, the rotation
caused by a molecule of one isomer is exactly
cancelled by an equal and opposite rotation caused by
a molecule of its enantiomer.
 An equal mixture of enantiomers called a racemic
mixture with prefix (±)
Example:
 if a given amount of (+) amphetamine causes the observed
rotation to be +6.250
 then an equal amount of (-) amphetamine under the same
conditions will result in an observed rotation of -6.250
 Thus, in mixing equal weights of the two enantiomers (a
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racemic mixture) we find that the net observed rotation is

zero.

Diastereomers
and Van't Hoff's Rule
 The Van't Hoff's Rule stated that:

"the maximum number of stereoisomers for a structure
with (n) different chiral centres is equal to 2n“
Examples:
 2-methyl-1-butanol has one chiral center (n=1) and two
enantiomers (2n =21 =2) OH
CH2
H C* CH3
CH2 CH3
 Enantiomers of 2-methyl-1-butanol
OH OH
CH2
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CH2
H C* CH3 CH3 C* H
CH2 CH3 CH2 CH3
116 (I) (II) General Chemistry - Dentistry

Diastereomers
 2,3,4-Trihydroxy-butanal has two unlike chiral centers
(n=2) and can therefore exist as four possible isomers
(2n =22 =4)
H O
C
H C* OH
H C* OH
CH2OH
 These four stereoisomers are
CHO CHO CHO CHO
H C* OH HO C* H H C* OH HO C* H
H C* OH HO C* H HO C* H H C* OH
CH2OH CH2OH CH2OH CH2OH
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(I) (II) (III) (IV)
enantiomers diastereomers enantiomers

Diastereomers
 Diastereomers: are stereoisomers that are not
mirror images of each other.
 Unlike enantiomers, which have the same physical
properties, Diastereomers have different boiling
points and melting points, refractive indices,
solubilities etc
Problem:
Give all stereoisomers of the following compounds:
1. 2-aminobutane
2. 3-nitro-2-butanol
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3. 2-amino-4-bromo-3-pentanol

Meso Compounds:
 A meso compound is an optically inactive compound
even though it possesses more than one chiral center.
COOH
Example *CHOH
 Tartaric acid *CHOH
COOH
 Tartaric acid has two chiral centers.

 According to the van't Hoff's rule, we could expect that tartaric acid
forms a maximum of four (22) stereoisomers.
 In fact there are only three possible stereoisomers for tartaric acid
as shown below:
COOH COOH COOH COOH
H C* OH HO C* H H C* OH HO C* H
HO C* H H C* OH H C* OH HO C* H
COOH
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COOH COOH COOH
(I) (II) (III) (IV)
enantiomers diastereomers identical (MESO)

Problems
1. Draw ALL stereoisomers of 3,4-dinitrobutane, and
indicate which isomers are enantiomers and which
are diastereomers or meso compounds.
2. Search the following web site in the internet for

further problems:
 http://www.chem.uic.edu/web1/OCOL-II/WIN/STEREO/11/FRAMES.HTM
 http://www.chem.uic.edu/web1/OCOL-II/WIN/STEREO/101/FRAMES.HTM
O. Attef 2008

Chemistry Lecture Notes 2010

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Chemistry Lecture Notes 2010

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Ajman University

Of Science And Technology Network

1 General Chemistry - Dentistry

 Credit Hours: 3 Credit Hours

2 General Chemistry - Dentistry

 Part II: Organic part will cover some important

3 General Chemistry - Dentistry

4 General Chemistry - Dentistry

6 General Chemistry - Dentistry

7 General Chemistry - Dentistry

8 General Chemistry - Dentistry

Mixtures Pure substances

heterogeneous homogeneous Elements Compounds

9 General Chemistry - Dentistry

10 General Chemistry - Dentistry

-Compare between compounds and mixtures.

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12 General Chemistry - Dentistry

13 General Chemistry - Dentistry

(Source: interactive CD, screen 2.4)

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 Dalton’s Atomic Theory:

See screen 2.5 on

• Isotopes in medicine (see Textbook, page 510)

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17 General Chemistry - Dentistry

cations anions cations anions

19 General Chemistry - Dentistry

- Solve tutorials on screens 2.17 -2.19 in Interactive CD

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- See online gallery of atomic orbitals at:

22 General Chemistry - Dentistry

 Classification of Elements, according to:

(See interactive CD, Tools: Periodic Table)

23 General Chemistry - Dentistry

 Electron configuration and the Periodic Table

- Textbook pages 156, 158 pp

- Solve tutorials on screens 6.17 -6.19 in Interactive CD

 Hybrid Orbitals: (examples)

 pz,pz-pi (π) bonds

25 General Chemistry - Dentistry

26 General Chemistry - Dentistry

Methods used to express relative amount of

(1) Mass percent g %:

27 General Chemistry - Dentistry

glucose dissolve in sufficient amount of water, then

weights of the solute.

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4. 0.5 M of acetic acid solution from 10 % acetic

5. Further Problems: see Textbook pp 95, and

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32 General Chemistry - Dentistry

 Formation of mixtures (alloys)

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34 General Chemistry - Dentistry

 Reaction with nonmetals: (S, X , O , N )

 Reaction with water

- Textbook pages 548 pp

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 Oxidizing agents and reducing agents

 Calculation of oxidation number (page

36 General Chemistry - Dentistry

 Practical uses of precipitation reactions