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Org Chem Intro

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Org Chem Intro

Uploaded by

Purani
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© © All Rights Reserved
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Unit 13

ORGANIC
CHEMISTRY
Aim #1 What is an organic compound and
what are its properties ?
 Organicchemistry 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?
 Has4 valence electrons, so it can bond 4 times to
achieve a stable octet
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?
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, 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)
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
2. Substitution
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

CH4 + Cl2  CH3Cl + HCl


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 CO2
Polymerization
When an unsaturated hydrocarbon called a monomer(one unit), bonds itself in
long chains creating a polymer(many units)

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

5CH2=CH2 → ( CH2-CH2 ) 5
Condensation Polymerization:
• Creation of a polymer plus water as a product

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