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Chemistry Introductory
Organic Chemistry
By
Professor AJAL.A.J
What is Chemistry ?
Composition
Chemistry
StructureProperties
What in the world isn’t Chemistry??
Branches of
chemistry
I. Physical chemistry
II. Organic chemistry
III. Inorganic chemistry
IV. Analytical chemistry
V. Industrial chemistry
VI. Bio chemistry
VII. Nuclear chemistry
VIII. Agricultural chemistry
IX. Geo chemistry
Uses of chemistry
Abuses of chemistry
War chemicals, brown sugar ,polyethylene
What is pencil lead made of if it isn't lead?
Pencil lead is a mixture of
graphite and clay.
Graphite is one form of the
element carbon.
Other forms of carbon are
diamond - the hardest naturally
occurring substance on the
earth, soot, charcoal and coke.
Organic Chemistry
“I used to experiment with
Chloroform as I wanted to get
into the subconscious mind. It
is a highly powerful state of
mind where you can memorise
quickly.”
“My mother made me a scientist without ever intending to. Every other Jewish mother in
Brooklyn would ask her child after school: So? Did you learn anything today? But not my
mother. “Izzy,” she would say, “did you ask a good question today?” That difference — asking
good questions — made me become a scientist.”
The Nobel Prize in Physics 1944 was awarded to Isidor Isaac
Rabi "for his resonance method for recording the magnetic
properties of atomic nuclei".
What is Organic chemistry?
The study of carbon and its compounds.
First we will concentrate on compounds just containing carbon
and hydrogen, these compounds are called hydrocarbons.
Hydrocarbon Classification
Hydrocarbons
Alkanes AlkenesCycloalkanes AlkynesCycloalkenes
IUPAC Naming Branched
Hydrocarbon Chains
Sometimes the hydrocarbon chains are
not straight and sometimes they have
other elements attached to them. Here is
how they are named:
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
Step 1: Find the longest continuous chain of
carbons.
1234567
There are 7 continuous carbons, so the parent chai
is heptane.
All bonds in the chain of carbons
are single bonds so ending is… ane.
• Step 2: Number the carbons in the main
sequence starting with the end that will give the
attached groups the smallest #.
This chain is numbered from right to left because
there is a substituent closest to the right.
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
1234567
1 2 3
4 5 6 7
• Step 3 : Add numbers to the names of the groups to
identify their positions on the chain.
- these numbers become prefixes to the parent chain.
In this ex. the positions are:
- methyl, - methyl, - ethyl
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
1234567
2 3 4
ethane
yl
C2H6
5
• Step 4: Use prefixes to indicate the appearance of a
group more than once in the structure.
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
1234567
Di =
Tri =
= four times
= five times
twice
three times
Tetra
Penta
• This chain has 2 methyl groups so
is used.
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
1234567
dimethyl
Step 5: List the alkyl groups in alphabetical order.
In this ex. dimethyl is listed before the ethyl.
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
1234567
Step 6: Use punctuation
- use commas to separate numbers
-hyphens to separate numbers with
words.
• The name of this compound is:
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
1234567
2,3-dimethyl – 4-ethyl heptane
Organic Chemistry- The study of
carbon & carbon compounds
• Organic compounds are the primary
constituents of all living organisms.
What makes carbon so special?
• It has a “central” role in all living organisms.
• It has 4 valence electrons.
• It makes 4 covalent bonds.
• It can bond with any
element,
but really loves to bond with other carbon atoms and
make long chains
CONTENTS
SPECIAL NATURE OF CARBON - CATENATION
CATENATION is the ability to form bonds between atoms of the same element.
Carbon forms chains and rings, with single, double and triple covalent bonds, because it is able to FORM
STRONG COVALENT BONDS WITH OTHER CARBON ATOMS
Carbon forms a vast number of carbon compounds because of the strength of the C-C covalent bond.
Other Group IV elements can do it but their chemistry is limited due to the weaker bond strength.
BOND ATOMIC RADIUS BOND ENTHALPY
C-C 0.077 nm +348 kJmol-1
Si-Si 0.117 nm +176 kJmol-1
The larger the atoms, the weaker the bond. Shielding due to filled inner orbitals and greater distance from the
nucleus means that the shared electron pair is held less strongly.
CONTENTS
COMMON FUNCTIONAL GROUPS
GROUP ENDING GENERAL FORMULA EXAMPLE
ALKANE - ane RH C2H6 ethane
ALKENE - ene C2H4 ethene
ALKYNE - yne C2H2 ethyne
HALOALKANE halo - RX C2H5Cl chloroethane
ALCOHOL - ol ROH C2H5OH ethanol
ALDEHYDE -al RCHO CH3CHO ethanal
KETONE - one RCOR CH3COCH3 propanone
CARBOXYLIC ACID - oic acid RCOOH CH3COOH ethanoic acid
ACYL CHLORIDE - oyl chloride RCOCl CH3COCl ethanoyl chloride
AMIDE - amide RCONH2 CH3CONH2 ethanamide
ESTER - yl - oate RCOOR CH3COOCH3 methyl ethanoate
NITRILE - nitrile RCN CH3CN ethanenitrile
AMINE - amine RNH2 CH3NH2 methylamine
NITRO nitro- RNO2 CH3NO2 nitromethane
SULPHONIC ACID - sulphonic acid RSO3H C6H5SO3H benzene sulphonic acid
ETHER - oxy - ane ROR C2H5OC2H5 ethoxyethane
CONTENTS
COMMON FUNCTIONAL GROUPS
ALKANE
ALKENE
ALKYNE
HALOALKANE
AMINE
NITRILE
ALCOHOL
ETHER
ALDEHYDE
KETONE
CARBOXYLIC ACID
ESTER
ACYL CHLORIDE
AMIDE
NITRO
SULPHONIC ACID
Silicon is similar to carbon. Why are there no
life forms based on silicon?
Silicon is unsuitable because, although it is a valence
IV element like carbon (4 electrons to share),
BUT the silicon-silicon covalent bond is not strong
enough for it to form long stable chains.
So, it can not form molecules of the complexity
needed to make up cells like carbon can!
Characteristics of Organic Compounds
• They are nonpolar compounds – they do not
dissolve in polar solvents like Water.
*remember the rule –
“likes dissolve likes”
O -
H + +H
• These plants and their flowers are
made up of a mixture of carbohydrates
that were manufactured from carbon
dioxide and water, with the energy of
sunlight. The simplest of the
carbohydrates are the
monosaccharides, simple sugars (fruit
sugar) that the plant synthesizes. Food
is stored as starches, which are
polysaccharides made from the simpler
monosaccharides. The plant structure
is held upright by fibers of cellulose,
another form of a polysaccharide.
• Ethylene is the gas that ripens fruit, and a ripe fruit emits the gas, which
will act on unripe fruit. Thus, a ripe tomato placed in a sealed bag with
green tomatoes will help ripen them.
• Crude oil from the ground is separated into usable groups of
hydrocarbons at this Louisiana refinery. Each petroleum
product has a boiling point range, or "cut," of distilled vapors that
collect in condensing towers.
• Refinery and tank storage facilities, like this one in Texas, are needed
to change the hydrocarbons of crude oil to many different petroleum
products. The classes and properties of hydrocarbons form one topic of
study in organic chemistry.
• Gasoline is a mixture of hydrocarbons (C8H18 for example) that contain
no atoms of oxygen. Gasohol contains ethyl alcohol, C2H5OH, which
does contain oxygen. The addition of alcohol to gasoline, therefore,
adds oxygen to the fuel. Since carbon monoxide forms when there is an
insufficient supply of oxygen, the addition of alcohol to gasoline helps
cut down on carbon monoxide emissions. An atmospheric inversion,
with increased air pollution, is likely during the dates shown on the
pump, so that is when the ethanol is added.
• These red ants, like other ants, make the simplest of the organic acids,
formic acid. The sting of bees, ants, and some plants contains formic
acid, along with some other irritating materials. Formic acid is
HCOOH.
I’m made of what???
• Guess how many elements your body is
made up of?
• 25 elements make up all living things
• About 97% of your body’s mass is made
of just 4 elements: oxygen, carbon,
hydrogen, & nitrogen.
• Two other major elements are
phosphorous & sulfur.
The most important element is…
• The word “organic” has lots of
meanings. Eventually, scientists
realized that the reactions occurring
inside the body could occur outside
it as well.
• They also learned how important
carbon is in all living things,
because of its ability to bond with
other atoms.
Acetylene gas welding and cutting
.
Aspirin ( a pain killer)
Paracetamol (fever reliever)
Insulin (hormone), produced by pancreas, used
in Diabetic Mellitus treatment
So, what do u think about table salt,
chlorophyll & hemoglobin ??
Polymers
.Teflon is polymer with a strong bond between carbon
and fluorine atoms. It is used as a no-stick surface in
cookware.
Cellulose in wood is extracted and converted to paper at
this plant in Maine. Microorganisms in the stomachs of
cows help them digest cellulose in plants.
Polysaccharides
Photosynthesis
Photosynthesis
Organic and
Biological
Chemistry
Chirality
• Carbons with four different groups attached to them are
handed, or chiral.
• Optical isomers or stereoisomers
• If one stereoisomer is “right-handed,” its enantiomer is “left-
handed.”
Organic and
Biological
Chemistry
Chirality
• Many pharmaceuticals are chiral.
• Often only one enantiomer is clinically active.
• Why?
S-ibuprofen
Organic and
Biological
Chemistry
Chirality
• Because they interact with a chiral protein binding site.
S-ibuprofen
Protein
Organic and
Biological
Chemistry
Amino Acids and Proteins
• Proteins are polymers of -
amino acids.
• A condensation reaction
between the amine end of
one amino acid and the acid
end of another produces a
peptide bond.
Organic and
Biological
Chemistry
Amino Acids and Proteins
• Hydrogen bonding in
peptide chains causes coils
and helices in the chain.
• Kinking and folding of the
coiled chain gives proteins
a characteristic shape.
Organic and
Biological
Chemistry
Amino Acids and Proteins
pyrophosphorylase
makes starch in plants
The complete molecule
is a tetramter. It’s
mass is 240,000 amu.
Organic and
Biological
Chemistry
Carbohydrates
Simple sugars are
polyhydroxy aldehydes or
ketones.
Organic and
Biological
Chemistry
Carbohydrates
• In solution they form
cyclic structures.
•These can form chains of sugars that form
structural molecules such as starch and
cellulose.
Organic and
Biological
Chemistry
Nucleic Acids
Two of the building blocks of RNA and DNA are
sugars (ribose or deoxyribose)
And cyclic bases (adenine,
guanine, cytosine, and
thymine or uracil).
Organic and
Biological
Chemistry
Nucleic Acids
These combine with a
phosphate to form a
nucleotide.
Organic and
Biological
Chemistry
Nucleic Acids
Nucleotides combine to
form the familiar double-
helix form of the nucleic
acids.
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Saturated hydrocarbons●
single
Alkanes = CnH2n+2
• A saturated hydrocarbon contains 20 carbons.
What is the formula?
C20H2(20)+2 = C20H42
• A saturated hydrocarbon contains 5 carbons.
What is the formula?
=C5H2(5)+2
Saturated = Single
C5H12
Alkanes
Alkanes
• CH4 = methane
• C2H6 = ethane
• C3H8 = propane
• C4H10 = butane
• C5H12 = pentane
< TARGET="display">
The smaller the compound the Lower Boiling point and
Melting point is (less bonds to break)
Naming Organic Compounds
• Organic compounds are named according to the
IUPAC (international union of pure & applied
chemistry) system of nomenclature.
Alkanes – end in
Alkenes – end in
Alkynes – end in
ane
ene
yne
Alkenes – CnH2n
series of unsaturated hydrocarbons having
one double bond (C=C)
• Also called ethylene series
(IUPAC name is ethene)
• General formula CnH2n
Alkenes
• C2H4 = Ethene
• C3H6 = Propene
• C4H8 = Butene
• C5H10 = Pentene
• To find the number of
hydrogens, double the
number of carbons.
1-Butene
This is 1-butene, because the double bond is
between the 1st and 2nd carbon from the end.
ISOMERS: Molecules have the same
molecular formula, but have different
structural formulas.
This is 1-pentene. The double bond is on the
first carbon from the end.
This is not another isomer of pentene. This is
also 2-pentene, just that the double bond is
closer to the right end.
Pentene
Alkynes –
a series of unsaturated hydrocarbons that
contain 1 triple bond.
• Also called the acetylene series
General formula CnH2n-2
C C
Alkynes
• C2H2 = Ethyne
• C3H4 = Propyne
• C4H6 = Butyne
• C5H8 = Pentyne
Alkyl Groups – have one less hydrogen
than the corresponding alkane.
• CH3 is methyl – one less H than
methane, CH4
C
H
H
H
H
Draw methyl
C2H5 is ethyl – one less H than ethane C2H6
Ethane
Condensed
Formula:
CH2CH3
C3H7 is propyl – one less H than propane C3H8
propane
Carbon forms Rings
• Carbon-based molecules also can be shaped like rings. Most carbon
rings contain 5 or 6 carbon atoms.
• One of the most important carbon rings is benzene.
• It has 6 carbons & 6 hydrogens , with alternating double bonds.
Carbon forms Rings
• Many compounds are based on Benzene.
• They often have very strong smells or aromas, so they are
called aromatic compounds.
• An example of one aromatic compound is a molecule called
vanillin.
• Guess what that smells like!
Benzene – a series of cyclic unsaturated
hydrocarbons.
General formula CnH2n-6
Benzene – C6H6 the simplest in the family
C
C
C
C
C
C H
H
H
H
H
H
review
Step 1: 6 carbons =
CH3 - CH2 – CH – CH2 – CH - CH3
123456
CH3 CH3
hex
All single bonds = ends in ane
hexane
Step 2: start numbering from right to left
Step 3: -methyl and -methyl2 4
So parent chain is
CH3 - CH2 – CH – CH2 – CH - CH3
123456
CH3 CH3
2,4 dimethyl hexane
C CC C C
CH3 CH3
1 2 3 4 5
3,4 dimethyl, 2-pentene
When naming with a double/triple bond-start #
carbons closest to the bond.
Now start with name and draw the structure.
• 3-ethylhexane
CC CC C C
CH2
CH3
You can place H’s all around or just leave as is.
ethane
yl
C2H6
5
C
C
HH
H H
H
• 2,2,4-trimethylpentane
C CC C C
CH3
CH3 CH3
Other Organic Compounds
Functional Groups – specific groupings of atoms that give
characteristic properties to organic compounds.
halides F (fluoro-)
Cl (chloro-)
Br (bromo-)
I (iodo-)
What group do these belong to?
Halogens
• Alcohols
• Organic acids
• Aldehydes
• Ketones
• Ethers
• Esters
• Amines
• Amides
-OH
-COOH
-CHO
-C-
-O-
-C-O
-N-
-C-NH
O
O
O
hydroxyl
carboxyl
carbonyl
Halides
Cmpds that are formed
when any halogen (F,Cl,Br,I)
replaces an H atom in an
alkane.
The functional group
is the halide (F,Cl,Br,I)
Halides
• They are named by citing the location of the halogen
attached to the chain
Drop the “ine” and add “o”
F
2- fluoropropane
Alcohols
• Are organic cmpds in which one or more of the
hydrogens is replaced with an – OH group.
- OH group is called the hydroxyl group
Monohydroxyl Alcohols
-have one –OH group
C
H
R
H
OH
Shortcut way to represent a primary alcohol
R-OH
R stands for REST of the molecule
IUPAC naming of alcohols
• Replace the final “e” with “-ol”
● methane methanol CH3OH
● ethane ethanol
● propane propanol
● butane butanol
● pentane pentanol
C2H5OH
C3H7OH
C4H9OH
C5H11OH
Ex. 2-propanol
C
H
H
HC
H
H
H C
OH
H
1 2 3
Organic acids – have the functional
group -COOH
• R-COOH
C
OH
O
Carboxyl
group
R
IUPAC naming of Organic Acids
 Replace the final “e” with “-oic ”acid
C
OH
O
Methanoic acid - HCOOH
C H
H
H
H
R
Aldehydes- contain the functional group -
CHO
R-CHO
C
H
O
R
IUPAC naming of Aldehydes-
• Replace the final “e” the the ending “al”
First member of the aldehyde family is methanal
-its common name is formaldehyde
C
H
O
H
1
2
3
4
Used to preserve
biological
samples
• Alcohols can be oxidized to aldehydes
C
H
R
H
OH + Oxidizing
agent
C
H
O
R + H20
methanol methanal water
Draw ethanal
C
H
O
C
H
H
H
Ketones – contain the functional group R-
CO-R
• The simplest member of the
ketone family is propanone.
 Replace the final “e” with “-one”.
• IUPAC name is propanone but its common
name is acetone, it is an important industrial
solvent.
C
H
H
C
H
H
H C
O
H
RR
Ethers -
• when two primary alcohols are treated with a
dehydrating agent, water is removed and the 2
alcohols are joined together by an oxygen
“bridge”.
R-OH + R-OH R-O-R + H20
Primary
alcohol
Primary
alcohol
ether
H2O
Diethyl ether- used as a general
anesthetic
C
H
H
C
H
H
H O H
ethylethyl
C
H
H
C
H
HOxygen bridge
-O-
Condensed formula
CH2CH3 CH2 CH3
Dimethyl ether-
C
H
H
C
H
H
H O H
methylmethyl
Oxygen bridge
-O-
Condensed formula
CH3 CH3
-O-
Condensed
formula CH3 CH2 CH3
Name These:
Methyl ethyl ether
-O-CH3 CH2 CH3
Ethyl propyl ether
CH2CH2
Esters – are organic cmpds with the
general formula R-CO-O-R
OC
O
They are formed in a rxn
between an organic acid and
an alcohol.
Esters have strong fragrant aromas and are what
make pineapples, bananas, wintergreen & oranges
so YummY!
Draw this:
IUPAC naming of Esters:
1. Look at chain after the –C-O- write its prefix
Ex.(meth,eth, etc.) and add –yl to the end of prefix
OC
O
C
H
H
H
C
H
H
C
H
H
C
H
H
H
O
In this ex. : eth + yl = ethyl
2. Give the name of the carbon chain that includes the
C=O, leave off the last letter and add –oate.
OC
O
C
H
H
H
C
H
H
C
H
H
C
H
H
H
Propane - 3 C’s and single bonds
Ethyl propanoate
propane + oate = propanoate
Condensed formula
CH3 CH2 COO CH2CH3
Ex.) Draw ethyl pentanoate
OC
O
C
H
H
H
C
H
H
C
H
H
C
H
H
HC
H
H
C
H
H
Now you’ve got it!
Amines – contain the functional group -N-
• It is a derivative of ammonia – NH3
• IUPAC naming of amines –
- replace the final –e with “-amine”
C
H
H
H
NH2 CC NH2
methanamine
ethanamine
Draw:
Amides – contain the functional
group:
• IUPAC naming of amides:
-drop the final –e and add “amide”
NHC
O
Found at the end of a carbon chain
C
H
H
NH2C C
O
H
H
H
propanamide
Amide
Synthetic Polyamides: nylon, kevlar
Natural Polyamide: silk!
butanamide
Organic Reactions
• Substitution – replacement of one kind of atom or
group with another atom or group
• If this rxn occurs between an alkane and a
halogen, it is called halogenation.
*only happens with alkanes –
single bonds!!!!
Substitution
Butane bromine
+ Br2
+
Br + HBr
Bromobutane
Hydrogen
bromide
+
C4H10 + Br2  C4H9Br + HBr
The second Br can then substitute for another H.
For Ex: Find the products of
C3H8 + F2  C3H7F + HF
Addition –adding one or more groups at
a double or triple bond.
• Double bond is broken…becomes a single
bond.
*only happens with alkenes & alkynes
– double/triple bonds!!!!
Addition
• Alkene + Halogen  Alkyl Halide
• The double bond is broken, and the halogen
adds at either side of where the double bond
was.
saturated
unsaturated
Fermentation
-Molecules are broken down
- enzymes act as catalysts
-Anaerobic respiration
glucose ethanol Carbon
dioxide
+
Esterification
• Organic Acid + Alcohol  Ester + Water
-COOH -OH -COO -H2O
-These are slow reversible reactions
-similar to neutralization rxn in inorganic
Acid + base = salt + water
Saponification – is the hydrolysis of fats by
bases.
• The breaking of an ester to produce an organic
acid plus an alcohol.
Fat + water = organic acid + glycerol
(glycerol ester) (soap) (alcohol)
What is this the reverse process of?
Organic Acid + Alcohol  Ester + Water
Esterification
Saponification - hydrolysis of an ester in
presence of a hot base (alkali)
Glycerol ester + 3 NaOH  soap + glycerol
Fat base alcohol soap
Polymers- are composed of many repeating
units of monomers
• Natural polymers
-starch – long chains of sugars
-proteins – long chains of amino acids
-cellulose – made of repeating units of sugar
starch cellulose
Polymers
• Synthetic (man made) polymers:
- nylon, rayon - polyester
- polyethylene - silicone
Polymerization- formation of polymers
from monomers
• Formation of larger molecules from smaller ones.
2 Methods :
1. Condensation polymerization: bonding of
monomers by dehydration synthesis
 Monomers have at least two functional groups
 -OH on ends
Condensation polymerization
Ex.)
C
H
H
HO C
H
H
HO
+ C
H
H
HO C
H
H
HO
monomer monomer
H2O
H2O
C
H
H
HO C
H
H
O
+C
H
H
C
H
H
HO
polymer
Leaves an oxygen
bridge
Addition Polymerization -
C C C C C C+ +
monomer monomer
monomer
CC CC C C
polymer
ethylene
ethylene
ethylene
polyethylene
Finding missing reactants & products in
organic rxns
• In balanced rxns the number of atoms on the left must
equal the number of atoms on the right.
C2H6Ex.) Cl2 C2H5Cl+ +
Left side Right side missing
C = C = C =
H = H = H =
Cl = Cl = Cl =
Missing product must be HCl
This is a substitution rxn because hydrogen atom of
ethane is replaced by chlorine.
2
6
2
2
5
1
0
1
1
• Try this one: C2H4Ex.) C2H4 Br2+
 What process makes…
fermentation
saponification
combustion
Condensation
polymerization
addition
polymerization
Br2
This is a addition rxn
Constitutional Isomers (Structural Isomers) are different compounds
of the same formula. The different structures from the previous slide for
the formula C4H10 is an example of Constitutional isomers.
Isomerism
Constitutional Isomers (Structural Isomers) are different compounds
of the same formula. The different structures from the previous slide for
the formula C4H10 is an example of Constitutional isomers.
How many isomers are there of an alkane containing five carbons
(C5H12)?
Isomerism
Isomer Strategy – Draw Lewis possible different length chains of
carbons atoms connected with a covalent bond.
Constitutional Isomers (Structural Isomers) are different compounds
of the same formula. The different structures from the previous slide for
the formula C4H10 is an example of Constitutional isomers.
How many isomers are there of an alkane containing five carbons
(C5H12)?
Isomerism
Isomer Strategy – Draw Lewis possible different length chains of
carbons atoms connected with a covalent bond.
C C C C C
Chains of 5 carbon atoms
H
H
HH
H HHH
HH
H H
What is an isomer?
• These compounds are
said to be isomers of one
another.
• Isomerism also occurs in
inorganic chemistry, but it
is less common.
If isomers have the same atoms in them, surely
they have the same properties, so what's the
point?
• In fact, these small changes in structure can have
significant effects on the properties of the substance!
• But, it is important to realize that this can have
significant effects in a living system.
• One optical isomer of glucose, for example, can be used
by a living cell, but the other isomer cannot.
• This is because the enzyme in the cell which recognizes
glucose is sensitive to only one form.
Isomerism
Diastereomers
(Chiral:
Non-superimposable
Non-Mirror Images;
multiple chiral centers)
Enantiomers
(Chiral:
Non-superimposable
Mirror Images)
There are two types of isomerism common in
organic chemistry:
1. structural isomerism
• Which have the atoms of their molecules
linked in a different order.
• This can come about in one of three
ways:
Chain Isomerism
• Chain isomers of the same compound are very similar.
• There may be small difference in physical properties such
as melting or boiling point due to different strengths of
intermolecular bonding.
• Their chemistry is likely to be identical.
Positional Isomers
• Positional isomers are also usually similar.
• There are slight physical differences, but the chemical
properties are usually very similar.
• However, occasionally, positional isomers can have quite
different properties
Functional Group Isomers
• Functional group isomers are likely to be both
physically and chemically dissimilar.
NOMENCLATURE
1. Common system
a. Works best for low molecular weight hydrocarbons
b. Steps to give a hydrocarbon a common name:
1. Count the total number of carbon atoms in the molecule.
2. Use the Latin root from the following slide that corresponds to the
number of carbon atoms followed by the suffix “ane”.
3. Unbranced hydrocarbons use the prefix normal, or n-,
4. Branched hydrocarbons use specific prefixes, as shown on a
subsequent slide
NOMENCLATURE
Common system Examples
CH C
H
H
H
H
C
H
H
H
1. Give a name for the following compound
Step #1, count the number of carbons and write down the memorized Latin name
for that number (next slide)
Step #2, since this structure fits the alkane general formula, use the “ane” suffix
propane
Three carbon Latin root
Alkane suffix
Latin
Hydrocarbon
Roots
Number of
Carbons
Latin
Root
1 meth
2 eth
3 prop
4 but
5 pent
6 hex
7 hept
8 oct
9 non
10 dec
11 undec
Latin
Hydrocarbon
Roots
Number of
Carbons
Latin
Root
12 dodec
13 tridec
14 tetradec
15 pentadec
16 hexadec
17 heptadec
18 octadec
19 nonadec
20 eicos
21 unicos
22 doicos
C
H
H
H
C
H
C
H
HH
C
H
H
H
CH
H
H
C
C
H H
C
H
H
H H
H
n-butane
isobutane
H C C C H
H C H
H C H
H
H
H
H
H
H
Examples
neopentane
mentorajal@gmail.com
890 730 5642
Contact your faculty
Thank you

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Organic Chemistry Essentials

  • 2.
  • 3.
  • 4. What is Chemistry ? Composition Chemistry StructureProperties What in the world isn’t Chemistry??
  • 5. Branches of chemistry I. Physical chemistry II. Organic chemistry III. Inorganic chemistry IV. Analytical chemistry V. Industrial chemistry VI. Bio chemistry VII. Nuclear chemistry VIII. Agricultural chemistry IX. Geo chemistry
  • 7. Abuses of chemistry War chemicals, brown sugar ,polyethylene
  • 8. What is pencil lead made of if it isn't lead? Pencil lead is a mixture of graphite and clay. Graphite is one form of the element carbon. Other forms of carbon are diamond - the hardest naturally occurring substance on the earth, soot, charcoal and coke.
  • 10. “I used to experiment with Chloroform as I wanted to get into the subconscious mind. It is a highly powerful state of mind where you can memorise quickly.”
  • 11.
  • 12. “My mother made me a scientist without ever intending to. Every other Jewish mother in Brooklyn would ask her child after school: So? Did you learn anything today? But not my mother. “Izzy,” she would say, “did you ask a good question today?” That difference — asking good questions — made me become a scientist.” The Nobel Prize in Physics 1944 was awarded to Isidor Isaac Rabi "for his resonance method for recording the magnetic properties of atomic nuclei".
  • 13.
  • 14. What is Organic chemistry? The study of carbon and its compounds. First we will concentrate on compounds just containing carbon and hydrogen, these compounds are called hydrocarbons. Hydrocarbon Classification Hydrocarbons Alkanes AlkenesCycloalkanes AlkynesCycloalkenes
  • 16. Sometimes the hydrocarbon chains are not straight and sometimes they have other elements attached to them. Here is how they are named: CH3 - CH2 - CH2 – CH – CH – CH - CH3 CH2 CH3 CH3 CH3
  • 17. CH3 - CH2 - CH2 – CH – CH – CH - CH3 CH2 CH3 CH3 CH3 Step 1: Find the longest continuous chain of carbons. 1234567 There are 7 continuous carbons, so the parent chai is heptane. All bonds in the chain of carbons are single bonds so ending is… ane.
  • 18. • Step 2: Number the carbons in the main sequence starting with the end that will give the attached groups the smallest #. This chain is numbered from right to left because there is a substituent closest to the right. CH3 - CH2 - CH2 – CH – CH – CH - CH3 CH2 CH3 CH3 CH3 1234567 1 2 3 4 5 6 7
  • 19. • Step 3 : Add numbers to the names of the groups to identify their positions on the chain. - these numbers become prefixes to the parent chain. In this ex. the positions are: - methyl, - methyl, - ethyl CH3 - CH2 - CH2 – CH – CH – CH - CH3 CH2 CH3 CH3 CH3 1234567 2 3 4 ethane yl C2H6 5
  • 20. • Step 4: Use prefixes to indicate the appearance of a group more than once in the structure. CH3 - CH2 - CH2 – CH – CH – CH - CH3 CH2 CH3 CH3 CH3 1234567 Di = Tri = = four times = five times twice three times Tetra Penta
  • 21. • This chain has 2 methyl groups so is used. CH3 - CH2 - CH2 – CH – CH – CH - CH3 CH2 CH3 CH3 CH3 1234567 dimethyl Step 5: List the alkyl groups in alphabetical order. In this ex. dimethyl is listed before the ethyl.
  • 22. CH3 - CH2 - CH2 – CH – CH – CH - CH3 CH2 CH3 CH3 CH3 1234567 Step 6: Use punctuation - use commas to separate numbers -hyphens to separate numbers with words.
  • 23. • The name of this compound is: CH3 - CH2 - CH2 – CH – CH – CH - CH3 CH2 CH3 CH3 CH3 1234567 2,3-dimethyl – 4-ethyl heptane
  • 24. Organic Chemistry- The study of carbon & carbon compounds • Organic compounds are the primary constituents of all living organisms.
  • 25. What makes carbon so special? • It has a “central” role in all living organisms. • It has 4 valence electrons. • It makes 4 covalent bonds. • It can bond with any element, but really loves to bond with other carbon atoms and make long chains
  • 26. CONTENTS SPECIAL NATURE OF CARBON - CATENATION CATENATION is the ability to form bonds between atoms of the same element. Carbon forms chains and rings, with single, double and triple covalent bonds, because it is able to FORM STRONG COVALENT BONDS WITH OTHER CARBON ATOMS Carbon forms a vast number of carbon compounds because of the strength of the C-C covalent bond. Other Group IV elements can do it but their chemistry is limited due to the weaker bond strength. BOND ATOMIC RADIUS BOND ENTHALPY C-C 0.077 nm +348 kJmol-1 Si-Si 0.117 nm +176 kJmol-1 The larger the atoms, the weaker the bond. Shielding due to filled inner orbitals and greater distance from the nucleus means that the shared electron pair is held less strongly.
  • 27. CONTENTS COMMON FUNCTIONAL GROUPS GROUP ENDING GENERAL FORMULA EXAMPLE ALKANE - ane RH C2H6 ethane ALKENE - ene C2H4 ethene ALKYNE - yne C2H2 ethyne HALOALKANE halo - RX C2H5Cl chloroethane ALCOHOL - ol ROH C2H5OH ethanol ALDEHYDE -al RCHO CH3CHO ethanal KETONE - one RCOR CH3COCH3 propanone CARBOXYLIC ACID - oic acid RCOOH CH3COOH ethanoic acid ACYL CHLORIDE - oyl chloride RCOCl CH3COCl ethanoyl chloride AMIDE - amide RCONH2 CH3CONH2 ethanamide ESTER - yl - oate RCOOR CH3COOCH3 methyl ethanoate NITRILE - nitrile RCN CH3CN ethanenitrile AMINE - amine RNH2 CH3NH2 methylamine NITRO nitro- RNO2 CH3NO2 nitromethane SULPHONIC ACID - sulphonic acid RSO3H C6H5SO3H benzene sulphonic acid ETHER - oxy - ane ROR C2H5OC2H5 ethoxyethane
  • 29. Silicon is similar to carbon. Why are there no life forms based on silicon? Silicon is unsuitable because, although it is a valence IV element like carbon (4 electrons to share), BUT the silicon-silicon covalent bond is not strong enough for it to form long stable chains. So, it can not form molecules of the complexity needed to make up cells like carbon can!
  • 30. Characteristics of Organic Compounds • They are nonpolar compounds – they do not dissolve in polar solvents like Water. *remember the rule – “likes dissolve likes” O - H + +H
  • 31.
  • 32. • These plants and their flowers are made up of a mixture of carbohydrates that were manufactured from carbon dioxide and water, with the energy of sunlight. The simplest of the carbohydrates are the monosaccharides, simple sugars (fruit sugar) that the plant synthesizes. Food is stored as starches, which are polysaccharides made from the simpler monosaccharides. The plant structure is held upright by fibers of cellulose, another form of a polysaccharide.
  • 33. • Ethylene is the gas that ripens fruit, and a ripe fruit emits the gas, which will act on unripe fruit. Thus, a ripe tomato placed in a sealed bag with green tomatoes will help ripen them.
  • 34. • Crude oil from the ground is separated into usable groups of hydrocarbons at this Louisiana refinery. Each petroleum product has a boiling point range, or "cut," of distilled vapors that collect in condensing towers.
  • 35. • Refinery and tank storage facilities, like this one in Texas, are needed to change the hydrocarbons of crude oil to many different petroleum products. The classes and properties of hydrocarbons form one topic of study in organic chemistry.
  • 36. • Gasoline is a mixture of hydrocarbons (C8H18 for example) that contain no atoms of oxygen. Gasohol contains ethyl alcohol, C2H5OH, which does contain oxygen. The addition of alcohol to gasoline, therefore, adds oxygen to the fuel. Since carbon monoxide forms when there is an insufficient supply of oxygen, the addition of alcohol to gasoline helps cut down on carbon monoxide emissions. An atmospheric inversion, with increased air pollution, is likely during the dates shown on the pump, so that is when the ethanol is added.
  • 37. • These red ants, like other ants, make the simplest of the organic acids, formic acid. The sting of bees, ants, and some plants contains formic acid, along with some other irritating materials. Formic acid is HCOOH.
  • 38. I’m made of what??? • Guess how many elements your body is made up of? • 25 elements make up all living things • About 97% of your body’s mass is made of just 4 elements: oxygen, carbon, hydrogen, & nitrogen. • Two other major elements are phosphorous & sulfur.
  • 39. The most important element is… • The word “organic” has lots of meanings. Eventually, scientists realized that the reactions occurring inside the body could occur outside it as well. • They also learned how important carbon is in all living things, because of its ability to bond with other atoms.
  • 40. Acetylene gas welding and cutting .
  • 41. Aspirin ( a pain killer)
  • 43. Insulin (hormone), produced by pancreas, used in Diabetic Mellitus treatment
  • 44. So, what do u think about table salt, chlorophyll & hemoglobin ??
  • 45. Polymers .Teflon is polymer with a strong bond between carbon and fluorine atoms. It is used as a no-stick surface in cookware.
  • 46. Cellulose in wood is extracted and converted to paper at this plant in Maine. Microorganisms in the stomachs of cows help them digest cellulose in plants. Polysaccharides
  • 49. Organic and Biological Chemistry Chirality • Carbons with four different groups attached to them are handed, or chiral. • Optical isomers or stereoisomers • If one stereoisomer is “right-handed,” its enantiomer is “left- handed.”
  • 50. Organic and Biological Chemistry Chirality • Many pharmaceuticals are chiral. • Often only one enantiomer is clinically active. • Why? S-ibuprofen
  • 51. Organic and Biological Chemistry Chirality • Because they interact with a chiral protein binding site. S-ibuprofen Protein
  • 52. Organic and Biological Chemistry Amino Acids and Proteins • Proteins are polymers of - amino acids. • A condensation reaction between the amine end of one amino acid and the acid end of another produces a peptide bond.
  • 53. Organic and Biological Chemistry Amino Acids and Proteins • Hydrogen bonding in peptide chains causes coils and helices in the chain. • Kinking and folding of the coiled chain gives proteins a characteristic shape.
  • 54. Organic and Biological Chemistry Amino Acids and Proteins pyrophosphorylase makes starch in plants The complete molecule is a tetramter. It’s mass is 240,000 amu.
  • 55. Organic and Biological Chemistry Carbohydrates Simple sugars are polyhydroxy aldehydes or ketones.
  • 56. Organic and Biological Chemistry Carbohydrates • In solution they form cyclic structures. •These can form chains of sugars that form structural molecules such as starch and cellulose.
  • 57. Organic and Biological Chemistry Nucleic Acids Two of the building blocks of RNA and DNA are sugars (ribose or deoxyribose) And cyclic bases (adenine, guanine, cytosine, and thymine or uracil).
  • 58. Organic and Biological Chemistry Nucleic Acids These combine with a phosphate to form a nucleotide.
  • 59. Organic and Biological Chemistry Nucleic Acids Nucleotides combine to form the familiar double- helix form of the nucleic acids.
  • 62. Alkanes = CnH2n+2 • A saturated hydrocarbon contains 20 carbons. What is the formula? C20H2(20)+2 = C20H42 • A saturated hydrocarbon contains 5 carbons. What is the formula? =C5H2(5)+2 Saturated = Single C5H12
  • 64. Alkanes • CH4 = methane • C2H6 = ethane • C3H8 = propane • C4H10 = butane • C5H12 = pentane
  • 65. < TARGET="display"> The smaller the compound the Lower Boiling point and Melting point is (less bonds to break)
  • 66. Naming Organic Compounds • Organic compounds are named according to the IUPAC (international union of pure & applied chemistry) system of nomenclature. Alkanes – end in Alkenes – end in Alkynes – end in ane ene yne
  • 67. Alkenes – CnH2n series of unsaturated hydrocarbons having one double bond (C=C) • Also called ethylene series (IUPAC name is ethene) • General formula CnH2n
  • 68. Alkenes • C2H4 = Ethene • C3H6 = Propene • C4H8 = Butene • C5H10 = Pentene • To find the number of hydrogens, double the number of carbons.
  • 69. 1-Butene This is 1-butene, because the double bond is between the 1st and 2nd carbon from the end. ISOMERS: Molecules have the same molecular formula, but have different structural formulas.
  • 70. This is 1-pentene. The double bond is on the first carbon from the end. This is not another isomer of pentene. This is also 2-pentene, just that the double bond is closer to the right end. Pentene
  • 71. Alkynes – a series of unsaturated hydrocarbons that contain 1 triple bond. • Also called the acetylene series General formula CnH2n-2 C C
  • 72. Alkynes • C2H2 = Ethyne • C3H4 = Propyne • C4H6 = Butyne • C5H8 = Pentyne
  • 73. Alkyl Groups – have one less hydrogen than the corresponding alkane. • CH3 is methyl – one less H than methane, CH4 C H H H H Draw methyl
  • 74. C2H5 is ethyl – one less H than ethane C2H6 Ethane Condensed Formula: CH2CH3
  • 75. C3H7 is propyl – one less H than propane C3H8 propane
  • 76. Carbon forms Rings • Carbon-based molecules also can be shaped like rings. Most carbon rings contain 5 or 6 carbon atoms. • One of the most important carbon rings is benzene. • It has 6 carbons & 6 hydrogens , with alternating double bonds.
  • 77. Carbon forms Rings • Many compounds are based on Benzene. • They often have very strong smells or aromas, so they are called aromatic compounds. • An example of one aromatic compound is a molecule called vanillin. • Guess what that smells like!
  • 78. Benzene – a series of cyclic unsaturated hydrocarbons. General formula CnH2n-6 Benzene – C6H6 the simplest in the family C C C C C C H H H H H H
  • 80. Step 1: 6 carbons = CH3 - CH2 – CH – CH2 – CH - CH3 123456 CH3 CH3 hex All single bonds = ends in ane hexane Step 2: start numbering from right to left Step 3: -methyl and -methyl2 4 So parent chain is
  • 81. CH3 - CH2 – CH – CH2 – CH - CH3 123456 CH3 CH3 2,4 dimethyl hexane
  • 82. C CC C C CH3 CH3 1 2 3 4 5 3,4 dimethyl, 2-pentene When naming with a double/triple bond-start # carbons closest to the bond.
  • 83. Now start with name and draw the structure. • 3-ethylhexane CC CC C C CH2 CH3 You can place H’s all around or just leave as is. ethane yl C2H6 5 C C HH H H H
  • 85. Other Organic Compounds Functional Groups – specific groupings of atoms that give characteristic properties to organic compounds. halides F (fluoro-) Cl (chloro-) Br (bromo-) I (iodo-) What group do these belong to? Halogens
  • 86. • Alcohols • Organic acids • Aldehydes • Ketones • Ethers • Esters • Amines • Amides -OH -COOH -CHO -C- -O- -C-O -N- -C-NH O O O hydroxyl carboxyl carbonyl
  • 87. Halides Cmpds that are formed when any halogen (F,Cl,Br,I) replaces an H atom in an alkane. The functional group is the halide (F,Cl,Br,I)
  • 88. Halides • They are named by citing the location of the halogen attached to the chain Drop the “ine” and add “o” F 2- fluoropropane
  • 89. Alcohols • Are organic cmpds in which one or more of the hydrogens is replaced with an – OH group. - OH group is called the hydroxyl group
  • 90. Monohydroxyl Alcohols -have one –OH group C H R H OH Shortcut way to represent a primary alcohol R-OH R stands for REST of the molecule
  • 91. IUPAC naming of alcohols • Replace the final “e” with “-ol” ● methane methanol CH3OH ● ethane ethanol ● propane propanol ● butane butanol ● pentane pentanol C2H5OH C3H7OH C4H9OH C5H11OH
  • 92.
  • 94. Organic acids – have the functional group -COOH • R-COOH C OH O Carboxyl group R
  • 95. IUPAC naming of Organic Acids  Replace the final “e” with “-oic ”acid C OH O Methanoic acid - HCOOH C H H H H R
  • 96. Aldehydes- contain the functional group - CHO R-CHO C H O R
  • 97. IUPAC naming of Aldehydes- • Replace the final “e” the the ending “al” First member of the aldehyde family is methanal -its common name is formaldehyde C H O H 1 2 3 4 Used to preserve biological samples
  • 98. • Alcohols can be oxidized to aldehydes C H R H OH + Oxidizing agent C H O R + H20 methanol methanal water
  • 100. Ketones – contain the functional group R- CO-R • The simplest member of the ketone family is propanone.  Replace the final “e” with “-one”.
  • 101. • IUPAC name is propanone but its common name is acetone, it is an important industrial solvent. C H H C H H H C O H RR
  • 102. Ethers - • when two primary alcohols are treated with a dehydrating agent, water is removed and the 2 alcohols are joined together by an oxygen “bridge”. R-OH + R-OH R-O-R + H20 Primary alcohol Primary alcohol ether H2O
  • 103. Diethyl ether- used as a general anesthetic C H H C H H H O H ethylethyl C H H C H HOxygen bridge -O- Condensed formula CH2CH3 CH2 CH3
  • 104. Dimethyl ether- C H H C H H H O H methylmethyl Oxygen bridge -O- Condensed formula CH3 CH3
  • 105. -O- Condensed formula CH3 CH2 CH3 Name These: Methyl ethyl ether -O-CH3 CH2 CH3 Ethyl propyl ether CH2CH2
  • 106. Esters – are organic cmpds with the general formula R-CO-O-R OC O They are formed in a rxn between an organic acid and an alcohol. Esters have strong fragrant aromas and are what make pineapples, bananas, wintergreen & oranges so YummY! Draw this:
  • 107. IUPAC naming of Esters: 1. Look at chain after the –C-O- write its prefix Ex.(meth,eth, etc.) and add –yl to the end of prefix OC O C H H H C H H C H H C H H H O In this ex. : eth + yl = ethyl
  • 108. 2. Give the name of the carbon chain that includes the C=O, leave off the last letter and add –oate. OC O C H H H C H H C H H C H H H Propane - 3 C’s and single bonds Ethyl propanoate propane + oate = propanoate Condensed formula CH3 CH2 COO CH2CH3
  • 109. Ex.) Draw ethyl pentanoate OC O C H H H C H H C H H C H H HC H H C H H Now you’ve got it!
  • 110. Amines – contain the functional group -N- • It is a derivative of ammonia – NH3 • IUPAC naming of amines – - replace the final –e with “-amine” C H H H NH2 CC NH2 methanamine ethanamine Draw:
  • 111. Amides – contain the functional group: • IUPAC naming of amides: -drop the final –e and add “amide” NHC O Found at the end of a carbon chain C H H NH2C C O H H H propanamide
  • 112. Amide Synthetic Polyamides: nylon, kevlar Natural Polyamide: silk! butanamide
  • 113. Organic Reactions • Substitution – replacement of one kind of atom or group with another atom or group • If this rxn occurs between an alkane and a halogen, it is called halogenation. *only happens with alkanes – single bonds!!!!
  • 114. Substitution Butane bromine + Br2 + Br + HBr Bromobutane Hydrogen bromide + C4H10 + Br2  C4H9Br + HBr The second Br can then substitute for another H. For Ex: Find the products of C3H8 + F2  C3H7F + HF
  • 115. Addition –adding one or more groups at a double or triple bond. • Double bond is broken…becomes a single bond. *only happens with alkenes & alkynes – double/triple bonds!!!!
  • 116. Addition • Alkene + Halogen  Alkyl Halide • The double bond is broken, and the halogen adds at either side of where the double bond was. saturated unsaturated
  • 117. Fermentation -Molecules are broken down - enzymes act as catalysts -Anaerobic respiration glucose ethanol Carbon dioxide +
  • 118. Esterification • Organic Acid + Alcohol  Ester + Water -COOH -OH -COO -H2O -These are slow reversible reactions -similar to neutralization rxn in inorganic Acid + base = salt + water
  • 119. Saponification – is the hydrolysis of fats by bases. • The breaking of an ester to produce an organic acid plus an alcohol. Fat + water = organic acid + glycerol (glycerol ester) (soap) (alcohol) What is this the reverse process of? Organic Acid + Alcohol  Ester + Water Esterification
  • 120. Saponification - hydrolysis of an ester in presence of a hot base (alkali) Glycerol ester + 3 NaOH  soap + glycerol Fat base alcohol soap
  • 121. Polymers- are composed of many repeating units of monomers • Natural polymers -starch – long chains of sugars -proteins – long chains of amino acids -cellulose – made of repeating units of sugar starch cellulose
  • 122. Polymers • Synthetic (man made) polymers: - nylon, rayon - polyester - polyethylene - silicone
  • 123. Polymerization- formation of polymers from monomers • Formation of larger molecules from smaller ones. 2 Methods : 1. Condensation polymerization: bonding of monomers by dehydration synthesis  Monomers have at least two functional groups  -OH on ends
  • 124. Condensation polymerization Ex.) C H H HO C H H HO + C H H HO C H H HO monomer monomer H2O H2O C H H HO C H H O +C H H C H H HO polymer Leaves an oxygen bridge
  • 125. Addition Polymerization - C C C C C C+ + monomer monomer monomer CC CC C C polymer ethylene ethylene ethylene polyethylene
  • 126. Finding missing reactants & products in organic rxns • In balanced rxns the number of atoms on the left must equal the number of atoms on the right. C2H6Ex.) Cl2 C2H5Cl+ + Left side Right side missing C = C = C = H = H = H = Cl = Cl = Cl = Missing product must be HCl This is a substitution rxn because hydrogen atom of ethane is replaced by chlorine. 2 6 2 2 5 1 0 1 1
  • 127. • Try this one: C2H4Ex.) C2H4 Br2+  What process makes… fermentation saponification combustion Condensation polymerization addition polymerization Br2 This is a addition rxn
  • 128. Constitutional Isomers (Structural Isomers) are different compounds of the same formula. The different structures from the previous slide for the formula C4H10 is an example of Constitutional isomers. Isomerism
  • 129. Constitutional Isomers (Structural Isomers) are different compounds of the same formula. The different structures from the previous slide for the formula C4H10 is an example of Constitutional isomers. How many isomers are there of an alkane containing five carbons (C5H12)? Isomerism Isomer Strategy – Draw Lewis possible different length chains of carbons atoms connected with a covalent bond.
  • 130. Constitutional Isomers (Structural Isomers) are different compounds of the same formula. The different structures from the previous slide for the formula C4H10 is an example of Constitutional isomers. How many isomers are there of an alkane containing five carbons (C5H12)? Isomerism Isomer Strategy – Draw Lewis possible different length chains of carbons atoms connected with a covalent bond. C C C C C Chains of 5 carbon atoms H H HH H HHH HH H H
  • 131. What is an isomer? • These compounds are said to be isomers of one another. • Isomerism also occurs in inorganic chemistry, but it is less common.
  • 132. If isomers have the same atoms in them, surely they have the same properties, so what's the point? • In fact, these small changes in structure can have significant effects on the properties of the substance! • But, it is important to realize that this can have significant effects in a living system. • One optical isomer of glucose, for example, can be used by a living cell, but the other isomer cannot. • This is because the enzyme in the cell which recognizes glucose is sensitive to only one form.
  • 133. Isomerism Diastereomers (Chiral: Non-superimposable Non-Mirror Images; multiple chiral centers) Enantiomers (Chiral: Non-superimposable Mirror Images)
  • 134. There are two types of isomerism common in organic chemistry: 1. structural isomerism • Which have the atoms of their molecules linked in a different order. • This can come about in one of three ways:
  • 135. Chain Isomerism • Chain isomers of the same compound are very similar. • There may be small difference in physical properties such as melting or boiling point due to different strengths of intermolecular bonding. • Their chemistry is likely to be identical.
  • 136. Positional Isomers • Positional isomers are also usually similar. • There are slight physical differences, but the chemical properties are usually very similar. • However, occasionally, positional isomers can have quite different properties
  • 137. Functional Group Isomers • Functional group isomers are likely to be both physically and chemically dissimilar.
  • 138. NOMENCLATURE 1. Common system a. Works best for low molecular weight hydrocarbons b. Steps to give a hydrocarbon a common name: 1. Count the total number of carbon atoms in the molecule. 2. Use the Latin root from the following slide that corresponds to the number of carbon atoms followed by the suffix “ane”. 3. Unbranced hydrocarbons use the prefix normal, or n-, 4. Branched hydrocarbons use specific prefixes, as shown on a subsequent slide
  • 139. NOMENCLATURE Common system Examples CH C H H H H C H H H 1. Give a name for the following compound Step #1, count the number of carbons and write down the memorized Latin name for that number (next slide) Step #2, since this structure fits the alkane general formula, use the “ane” suffix propane Three carbon Latin root Alkane suffix
  • 140. Latin Hydrocarbon Roots Number of Carbons Latin Root 1 meth 2 eth 3 prop 4 but 5 pent 6 hex 7 hept 8 oct 9 non 10 dec 11 undec Latin Hydrocarbon Roots Number of Carbons Latin Root 12 dodec 13 tridec 14 tetradec 15 pentadec 16 hexadec 17 heptadec 18 octadec 19 nonadec 20 eicos 21 unicos 22 doicos C H H H C H C H HH C H H H CH H H C C H H C H H H H H n-butane isobutane H C C C H H C H H C H H H H H H H Examples neopentane