Organic Chemistry Fundamentals
Unit 13
ORGANIC
CHEMISTRY
Aim #1 What is an organic
compound and what are its
properties ?
Organic chemistry
is the study of
carbon
and its
compounds
found in fossil fuels, plants, animals
Examples include: gasoline, oil, sugars
Hydrocarbon
– contains only the elements H & C
(TABLE Q)
Therefore, hydrocarbons are organic, but not all
organic compounds are hydrocarbons
Why is carbon so special?
Has 4 valence electrons, so it can bond 4
times to achieve a stable octet
1.
Nonelectrolytes
(do not conduct
electricity)
2.
React
slowly
because they are
covalent
(nonmetal +
nonmetal)
3.
Usually low melting
point and boiling
point
4.
Insoluble and
immiscible in water
PROPERTIES OF
ORGANIC
COMPOUNDS
1.
Which of the following are organic?
2.
Which of the following are
hydrocarbons?
Types of Chemical Formulas
Molecular Formula
- shows the
# of atoms
of
each element in a compound (least
informative formula)
Ex. Propane = C
3
H
8
Types of Chemical Formulas
Structural Formula-
shows the
number of
atoms of each element
AND
the
arrangement of the atoms
; most informative
formula
Ex. Propane =
Types of Chemical Formulas
Condensed/Collapsed Formula-
combination of both
structural and
molecular formulas
-each carbon is written with its constituent
hydrogens
followed by the proper
subscript
Ex. Propane = CH
3
CH
2
CH
3
HOMOLOGOUS SERIES
Table Q shows the general formulas and structures for 3
families of hydrocarbons
1.
Alkanes-
single bonded hydrocarbons contains
ONLY (C-C)
These bonds are considered saturated. They have
the maximum number of hydrogens attached.
Remember that each bond represents 1 pair of
shared electrons (2 e- total per bond)
General formula: C
n
H
2n+2
Example: Methane
2. Alkenes-
double bonded hydrocarbons,
contains (C=C)
These bonds are considered unsaturated
General formula: C
n
H
2n
Example: Butene
3.
Alkynes
– triple bonded hydrocarbons,
contains (C- C triple bonds)
These bonds are considered unsaturated
General formula C
n
H
2n-2
Example: Propyne
How can we name hydrocarbons? -
IUPAC
To name simple hydrocarbons (straight chain,
only C and H), we will put information from
Table P and Table Q together
Table P shows the
prefix
to determine
how many
carbons
are in a
compound
Ex) Give the prefixes for the following:
C
2
H
6
C
4
H
6
C
5
H
12
C
7
H
14
C
8
H
18
C
10
H
20
How can we name hydrocarbons? -
IUPAC
Steps in naming simple (unbranched)
hydrocarbons:
1.
How many
carbon
atoms are in the
longest
continuous chain
? Find the prefix for this
from Table P.
2.
If it is an
alkane
, simply add the suffix
“
-ane
”
to the name.
How can we name hydrocarbons? -
IUPAC
3. If it is an
alkene
, you must first indicate the
location of the double bond
(s) if the molecule has
more than 3 Cs. Do this by numbering the
carbons on the chain and stating the l
owest
carbon #
where the
double bond is located
. Then
add the suffix “
-
ene
” to the name.
How can we name hydrocarbons? -
IUPAC
4. If it is an
alkyne
, you must first indicate the
location of the triple bond(s
) if the molecule has
more than 3 Cs. Do this by numbering the
carbons on the chain and stating the lowest
carbon # where the triple bond is located. Then
add the suffix
“
-yne
”
to the name.
Aim # 3 What are isomers?
Isomers have the same
molecular
formula but
are rearranged in a different
structure
with
different
chemical and physical properties.
•
At least
4 carbons
must be present in a
molecule to have isomers
•
Methane, ethane, and propane
DO NOT
have any isomers
What are isomers?
Butane is the first molecule to have isomers. The
larger
the molecule (the more carbon atoms),
the more isomers the molecule will have
3 ways to make an isomer:
1. Make a branch (on a non-terminal
carbon)
2. Move a branch
3. Move a multiple bond (a double or
triple bond)
What are isomers?
Pentane Isomers
What are isomers?
Pentene Isomers
Aim # 4 How can we name &
draw substituted hydrocarbons?
1.
Count the longest
parent chain
of carbon atoms –
name that chain
2.
Scan the chain and take note of anything that is
not a
C or H
3.
Indicate the lowest number carbon that has the
substitution
4.
Name the substitution (F-fluoro, Cl-chloro, Br- bromo, I-
iodo, CH
3
- methyl, CH
2
- ethyl)
Notice that if there are more than one substitutions,
you must indicate all of their locations (which # C
they’re attached to), and put a numerical prefix in
front of the substitution name (“
di-
” for 2, “
tri-
” for 3,
“
tetra-
” for 4)
How can we name and draw
substituted hydrocarbons?
chloromethane
How can we name and draw
substituted hydrocarbons?
dichloromethane
How can we name and draw
substituted hydrocarbons?
F H
H - C – C – H
H H
1-fluoroethane
How can we name and draw
substituted hydrocarbons?
1,1 -difluoroethane
How can we name and draw
substituted hydrocarbons?
F H
H - C – C – H
H F
1,2 - difluoroethane
How can we name and draw
substituted hydrocarbons?
1-fluoro, 1,2 – dibromo ethane
How can we name and draw
substituted hydrocarbons?
1,2 – dichloropropane
How can we name and draw
substituted hydrocarbons?
1,3 - dicholoropropane
How can we name and draw
substituted hydrocarbons?
2-methylpropane
How can we name and draw
substituted hydrocarbons?
2,2 – dimethyl butane
How can we name and draw
substituted hydrocarbons?
2, 2, 3 – trimethyl pentane
Aim # 5 What are functional
groups?
Although hydrocarbons are the most basic
organic compounds, many other organic
compounds form when other atoms replace one
or more hydrogen atoms in a hydrocarbon
These atoms or groups of atoms, called
functional
groups
, replace hydrogen atoms in a
hydrocarbon and give the compound distinctive
physical and chemical properties
The naming of these compounds is made easy
because they derive their names from the
hydrocarbon with the corresponding number of
carbon atoms
Halides-
Have one of the
halogens
as a branched group
F (fluoro)
Cl (chloro)
Br (bromo)
I (iodo)
Fluoromethane
1, 2 dibromo ethane
Chloromethane
Alcohols
a)
Have an
–OH
group
b)
Flammable, soluble
c)
NOT bases (covalently bonded) and NOT
electrolytes
d)
Has the suffix
“-ol”
and must also state the location of
the –OH along the carbon chain (using lowest #
location)
Organic Acids
a)
Have a
carboxyl group (-COOH)
at the last
carbon
b)
Also known as
carboxylic acids
: weak acids/weak
electrolytes because they generate
H
+
ions
in solution
c)
Has the suffix
“-oic acid”
Aldehydes
a)
CHO group found
at the end
of the
hydrocarbon chain
b)
Soluble and reactive
c)
Has the suffix
“-al”
Ketones
a)
CO group located on an
interior carbon
atom
a)
Can NEVER be a terminal carbon, or
it would be an aldehyde!
b)
Has the suffix
“-one”
c)
Somewhat soluble, needs at least 3
carbons
Ester
a)
Contains COO
connecting parent chain to branch
a)
Smell nice! Found in perfumes, foods
b)
Has the suffix
-anoate
Amine
a)
Nitrogen is present
b)
Used in dyes
, found in proteins,
DNA
c)
Has the suffix
-
amine
Amide
propanamide
a)
Contains
b)
Used in dyes
c)
Has the suffix -
amide
Ether
Dimethyl ether
Methyl ethyl ether
a) look for
–O-
somewhere in the
middle
b) anesthetic, soluble
c) Name small chain, then the large
chain and follow with suffix
“-ether
”
Aromatic Hydrocarbons
a)
6 carbons are in a closed ring with alternating double and single
bonds
b) Called benzene
c) It is very stable
d) Can be substituted
Methylbenzene
1,4-dichloro benzene
Aim # 6 What are the
different organic reactions?
1. Combustion
a)
In the presence of oxygen:
A hydrocarbon and oxygen produces CO
2
and water
In limited oxygen:
A hydrocarbon and oxygen produce CO and Water
2. Substitution
CH
4
+ Cl
2
CH
3
Cl + HCl
a)
Involves a saturated hydrocarbon
b)
One or more H gets replaced by another atom or group
c)
Compare the number of H on the reactant and product
side
3. Addition
a.
Involves an unsaturated hydrocarbon, atoms/
groups are added in at a multiple bond site.
Unsaturated hydrocarbon
saturated
hydrocarbon
b.
Hint: look for 2 reactants and one product
4. Esterification
•
An
organic acid
and
alcohol
makes an
ester
and
water
•
Should be able to recognize the acid group and the
hydroxyl group in the reactants
•
Hint: table R to recognize the ester in the products
5. Saponification
•
A
fat
reacts with a
base
to produce
and alcohol (look for glycerol) and a
soap
Fermentation
•
Glucose yields ethanol and CO
2
Polymerization
5CH
2
=CH
2
→ ( CH
2
-CH
2
) 5
Addition Polymerization:
•
Unsaturated monomers join by breaking their double
or triple bonds to bond with one another, making
long chains
•
Several monomers combine to make the polymer
Condensation Polymerization:
•
Creation of a polymer plus water as a product
When an
unsaturated
hydrocarbon called a
monomer
(one unit),
bonds itself in long chains creating a
polymer
(many units)
Delve into the world of organic chemistry, understanding the nature of organic compounds, the unique attributes of carbon, and the properties of these compounds. Discover the significance of molecular, structural, and condensed formulas, along with insights into hydrocarbons and the concept of homologous series.
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Presentation Transcript
Unit 13 ORGANIC CHEMISTRY
Aim #1 What is an organic compound and what are its properties ? Organic chemistry is the study of carbon and its compounds found in fossil fuels, plants, animals Examples include: gasoline, oil, sugars Hydrocarbon contains only the elements H & C (TABLE Q) Therefore, hydrocarbons are organic, but not all organic compounds are hydrocarbons
Why is carbon so special? Has 4 valence electrons, so it can bond 4 times to achieve a stable octet
1. Nonelectrolytes (do not conduct electricity) 2. React slowly because they are covalent (nonmetal + nonmetal) 3. Usually low melting point and boiling point 4. Insoluble and immiscible in water PROPERTIES OF ORGANIC COMPOUNDS
1. Which of the following are organic? 2. Which of the following are hydrocarbons?
Types of Chemical Formulas Molecular Formula- shows the # of atoms of each element in a compound (least informative formula) Ex. Propane = C3H8
Types of Chemical Formulas Structural Formula- shows the number of atoms of each element AND the arrangement of the atoms; most informative formula Ex. Propane =
Types of Chemical Formulas Condensed/Collapsed Formula- combination of both structural and molecular formulas -each carbon is written with its constituent hydrogens followed by the proper subscript Ex. Propane = CH3CH2CH3
Structural Formula Condensed Formula CH3C2CH3
HOMOLOGOUS SERIES Table Q shows the general formulas and structures for 3 families of hydrocarbons
1. Alkanes- single bonded hydrocarbons contains ONLY (C-C) These bonds are considered saturated. They have the maximum number of hydrogens attached. Remember that each bond represents 1 pair of shared electrons (2 e- total per bond) General formula: CnH2n+2 Example: Methane
2. Alkenes- double bonded hydrocarbons, contains (C=C) These bonds are considered unsaturated General formula: CnH2n Example: Butene
3. Alkynes triple bonded hydrocarbons, contains (C- C triple bonds) These bonds are considered unsaturated General formula CnH2n-2 Example: Propyne
How can we name hydrocarbons? - IUPAC To name simple hydrocarbons (straight chain, only C and H), we will put information from Table P and Table Q together Table P shows the prefix to determine how many carbons are in a compound Ex) Give the prefixes for the following: C2H6 C4H6 C5H12 C7H14 C8H18 C10H20
How can we name hydrocarbons? - IUPAC Steps in naming simple (unbranched) hydrocarbons: 1. How many carbon atoms are in the longest continuous chain? Find the prefix for this from Table P. 2. If it is an alkane, simply add the suffix -ane to the name.
How can we name hydrocarbons? - IUPAC 3. If it is an alkene, you must first indicate the location of the double bond(s) if the molecule has more than 3 Cs. Do this by numbering the carbons on the chain and stating the lowest carbon # where the double bond is located. Then add the suffix -ene to the name.
How can we name hydrocarbons? - IUPAC 4. If it is an alkyne, you must first indicate the location of the triple bond(s) if the molecule has more than 3 Cs. Do this by numbering the carbons on the chain and stating the lowest carbon # where the triple bond is located. Then add the suffix -yne to the name.
Aim # 3 What are isomers? Isomers have the same molecular formula but are rearranged in a different structure with different chemical and physical properties. At least 4 carbons must be present in a molecule to have isomers Methane, ethane, and propane DO NOT have any isomers
What are isomers? Butane is the first molecule to have isomers. The larger the molecule (the more carbon atoms), the more isomers the molecule will have 3 ways to make an isomer: 1. Make a branch (on a non-terminal carbon) 2. Move a branch 3. Move a multiple bond (a double or triple bond)
What are isomers? Pentane Isomers
What are isomers? Pentene Isomers
Aim # 4 How can we name & draw substituted hydrocarbons? Count the longest parent chain of carbon atoms name that chain Scan the chain and take note of anything that is not a C or H Indicate the lowest number carbon that has the substitution Name the substitution (F-fluoro, Cl-chloro, Br- bromo, I- iodo, CH3- methyl, CH2 - ethyl) Notice that if there are more than one substitutions, you must indicate all of their locations (which # C they re attached to), and put a numerical prefix in front of the substitution name ( di- for 2, tri- for 3, tetra- for 4) 1. 2. 3. 4.
How can we name and draw substituted hydrocarbons? chloromethane
How can we name and draw substituted hydrocarbons? dichloromethane
How can we name and draw substituted hydrocarbons? F H H - C C H H H 1-fluoroethane
How can we name and draw substituted hydrocarbons? 1,1 -difluoroethane
How can we name and draw substituted hydrocarbons? F H H - C C H H F 1,2 - difluoroethane
How can we name and draw substituted hydrocarbons? 1-fluoro, 1,2 dibromo ethane
How can we name and draw substituted hydrocarbons? 1,2 dichloropropane
How can we name and draw substituted hydrocarbons? 1,3 - dicholoropropane
How can we name and draw substituted hydrocarbons? 2-methylpropane
How can we name and draw substituted hydrocarbons? 2,2 dimethyl butane
How can we name and draw substituted hydrocarbons? 2, 2, 3 trimethyl pentane
Aim # 5 What are functional groups? Although hydrocarbons are the most basic organic compounds, many other organic compounds form when other atoms replace one or more hydrogen atoms in a hydrocarbon These atoms or groups of atoms, called functional groups, replace hydrogen atoms in a hydrocarbon and give the compound distinctive physical and chemical properties The naming of these compounds is made easy because they derive their names from the hydrocarbon with the corresponding number of carbon atoms
Halides- Have one of the halogens as a branched group F (fluoro) Cl (chloro) Br (bromo) I (iodo)
Chloromethane Fluoromethane 1, 2 dibromo ethane
Alcohols a) Have an OH group b) Flammable, soluble c) NOT bases (covalently bonded) and NOT electrolytes d) Has the suffix -ol and must also state the location of the OH along the carbon chain (using lowest # location)
Organic Acids a) Have a carboxyl group (-COOH) at the last carbon b) Also known as carboxylic acids: weak acids/weak electrolytes because they generate H+ ions in solution c) Has the suffix -oic acid
Aldehydes a) CHO group found at the end of the hydrocarbon chain b) Soluble and reactive c) Has the suffix -al
Ketones a) CO group located on an interior carbon atom a) Can NEVER be a terminal carbon, or it would be an aldehyde! b) Has the suffix -one c) Somewhat soluble, needs at least 3 carbons
Ester a) Contains COO connecting parent chain to branch a) Smell nice! Found in perfumes, foods b) Has the suffix -anoate
Amine a) Nitrogen is present b) Used in dyes, found in proteins, DNA c) Has the suffix -amine
Amide a)Contains b)Used in dyes c)Has the suffix -amide propanamide
Ether Dimethyl ether a) look for O- somewhere in the middle b) anesthetic, soluble c) Name small chain, then the large chain and follow with suffix -ether Methyl ethyl ether
Aromatic Hydrocarbons a) 6 carbons are in a closed ring with alternating double and single bonds b) Called benzene c) It is very stable d) Can be substituted Methylbenzene 1,4-dichloro benzene
Aim # 6 What are the different organic reactions?
1. Combustion a) In the presence of oxygen: A hydrocarbon and oxygen produces CO2 and water In limited oxygen: A hydrocarbon and oxygen produce CO and Water
