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Organic Chemistry
BELL RINGER
What makes
a compound
organic?
Origin of organic compounds
• Naturally occurring organic compounds are
found in plants, animals, and fossil fuels
• All of these have a plant origin
• All of these rely on the “fixing” of C from CO2
• Synthetic organic compounds are derived
from fossil fuels or plant material
Introduction
•
•
•
•
Most current research focuses on Organic
Originally from “organic” meaning life
Not just chemistry of life, chemistry of carbon
Exceptions:
– oxides of carbon (CO2, CO)
– carbonates,bicarbonates(NaHCO3,CaCO3)
– cyanides (NaCN, etc)
One C with no H, or with metal
• Carbon can form four bonds…
C C C
C
C
Properties of Organic Compounds
1.
2.
3.
4.
5.
6.
7.
Covalently bonded
Low Melting Points
Non-electrolytes
Nonpolar
React slower than inorganic compounds
Require high activation energies
Insoluble in water ~ generally
Carbon forms four bonds
• Carbon can form four bonds, and forms
strong covalent bonds with other elements
• This can be represented in many ways …
H
O
C
C
H
Cl
C
CH
C
Cl
H
CH2
H3C
Cl
C
C
H3C
CH3
CH
CH
CH2
CH2
CH3 CH3
CH3 CH3
CH
CH2
CH2
CH2
CH2
CH3
CH2
Functional groups
• Functional groups are parts of molecules that
result in characteristic features
• About 100 functional groups exist, we will
focus on about 10
• Useful to group the infinite number of possible
organic compounds
• Ex - the simplest group is hydrocarbons
• Made up of only C and H
• Not really a functional “group”
• Further divided into:
»Aliphatics - Alkanes, Alkenes, Alkynes
»Aromatics
Hydrocarbons
Alkanes C
CnH2n+2
H
H
C
H
H
C
H
H
C
H
Alkynes C
CnH2n-2
H
C
C
C
H
C
H
Alkenes
CnH2n
C
H
H
H
H
H
C
H
H
C
C
C
C
C
C
H
H
H
H
H
Aromatics
C
H
H
H
H
C
C
C
H
H
H
H
H
H
H
C
C
C
C
H
C
C
H
H
Naming Hydrocarbons
(nomenclature)
Drawing structures: it’s all good
2-butene
H
H
H
C
H
C
C
C
C
H
H
H
H
H
H3C CH CH CH3
H3C
CH3
C
H
CH
H3C
CH3
CH
This is called the
“condensed structure” On a test, choose a method
that shows all H’s
CH3CH=CHCH3
Using brackets can also shorten some formulas:
CH3(CH2)4CH3 vs. CH3CH2CH2CH2CH2CH3
Draw/Name the following
Octane
1-hexyne
H
H
H
H
H
H
H
H
H
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
C
C
C
C
C
C
H
H
H
H
H
H
H
Propene
2-pentene
H
H
C
C
C
H
H
H
H
H
H
C
C
C
C
C
H
H
H
H
H
H
H
H
BELL RINGER
What is the structural
formula for 2-hexene
CH3CHCHCH2CH2CH3
Hydroxyl, carbonyl, carboxyl
• There are other names that describe patterns
of atoms that are parts of functional groups.
• “Hydroxyl” refers to –OH
• “Carbonyl” refers to C=O
• “Carboxyl” refers to COOH
Naming: common vs. IUPAC
• Common names used in the 1800’s are still
used for some compounds today:
O
O
C
C
H
OH
Formic acid
H
H3C
CH3
Acetone
C
C
Acetylene
H
• The International Union of Pure and Applied
Chemistry (IUPAC) was established in 1900s
Numbering carbons
Q- draw pentene
A- Where’s the bond? H C
3
5
1
We number C atoms
H
H
1-pentene
C
C
C
C
H
H
H
H
4
2
3
2
4
1
5
H
• Thus, naming compounds with multiple bonds
is more complex than previously indicated
• Only if 2+ possibilities exist, are #s needed
• Always give double bond the lowest number
H
• Try to name these:
C2H4
H3 C
C
C
2-butene
CH3
Ethene
H
CH3CH2CCCH2CH2CH2CH2CH3 3-nonyne
Branched Hydrocarbons
CH3
CH3
H3C
• Names are made up
of: side chains, root
• 2,3-dimethylpentane
CH3
• Root is the longest possible HC chain
• Must contain multiple bonds if present
• Add -yl to get name of side chain H C
CH3
3
• Common side chains include:
CH
CH3- methyl
CH3CH2- ethyl
*
CH3CH2CH2- propyl (CH3)2CH• isopropyl
Br- (bromo), Cl- (chloro), F- (fluoro), I- (iodo)
Naming side chains
CH3
CH3 CH2 CH
CH2 CH3
CH2 C
CH3
CH3
Rule 1: choose the correct ending
-ane
Naming side chains
CH3
CH3 CH2 CH
CH2 CH3
CH2 C
CH3
CH3
Rule 2: longest carbon chain
ane
Naming side chains
CH3
CH3 CH2 CH
CH2 CH3
CH2 C
CH3
CH3
Rule 3: attach prefix (according to # of C)
Heptane
ane
Naming side chains
CH3
CH2 CH3
2
CH3 CH2 CH
C
CH2 C
7
4
6
5
3
1
CH3
CH3
Rule 4: Assign numbers to each carbon
heptane
Naming side chains
methyl
CH 3
CH3 CH2 CH
C
7
6
5
CH2 CH3
2
CH2 C
4
3
CH3
1
CH3
methyl
methyl
Rule 5: Determine name for side chains
heptane
Naming side chains
methyl
CH3
CH2 CH3
2
CH3 CH2 CH
CH2 C
7
4
6
5
3
CH3
1
CH3
methyl
methyl
Rule 6: attach name of branches
3-methyl-3-methyl-5-methyl-heptane
Naming side chains
methyl
CH3
CH2 CH3
2
CH3 CH2 CH
CH2 C
7
4
6
5
3
CH3
1
CH3
methyl
methyl
Rule 8,9: group similar branches
3-methyl-3-methyl-5-methyl-heptane
Naming side chains
methyl
CH3
CH2 CH3
2
CH3 CH2 CH
CH2 C
7
4
6
5
3
CH3
1
CH3
methyl
methyl
Rule 8,9: group similar branches
3,3,5-trimethyl-heptane
BELL RINGER
Name the
hydrocarbon
H
H
H
H C H H C H
H HH C H H C H
H C–C–C–C=C–C H
H H
H
H
H C H
4-ethyl-3-methyl-4-octene
H
Naming side chains
H3C
H3C
CH2
CH CH3
H2C
CH2
CH CH CH2 CH3
H3C
CH3
3-methylhexane
CH2 CH2 CH3
CH
CH3
4-ethyl-2,3-dimethylheptane
CH3
CH3
CH3
CH3 CH2 CH CH CH CH2 CH CH3
CH2 CH3
5-ethyl-2,4,6-trimethyloctane
Functional Groups
Alcohols
Element Grouping:
Naming:
Example:
-OH
-name ends in –ol
OH
CH3 CH2 CH CH3
2-butanol
Functional Groups
Alcohols
Ethylene glycol  1,2 Ethanediol
HO
H
H
C
C
H
H
OH
Odorless, colorless, sweet and
syrupy, toxic liquid
Functional Groups
Aldehydes
Element Grouping:
Naming:
O
C H
-name ends in –al
O
Example:
H3C
C
H
ethanal
Functional Groups
Ketones
Element Grouping:
Naming:
Example:
O
C
-name ends in –one
O
H3C
C
CH3
propanone
Functional Groups
Organic Acids
Element Grouping:
O
C OH
Naming: -name ends in
–oic acid
O
Example:
CH3 CH2 CH2 C
OH
butanoic acid
BELL RINGER
Name the following organic compound:
H
H H
O
H
H
H C–C–C–C–C–C H
H
H
H
3-hexanone
H
H
Functional Groups
Ethers
Element Grouping:
Naming:
Example:
-O-name ends in ether
H 3C
O
CH 2 CH 2 CH 3
methyl propyl ether
Functional Groups
Halides
Element Grouping:
C Cl
C Br
C F
C I
Naming: -use prefix with o ending
Cl
Example:
CH3-CH-CH-CH3
F
2-chloro-3-fluoro-butane
Functional Groups
Amine
Element Grouping:
N
Naming: -name ends in
Example:
–amine
CH 3 CH 2 CH 2 NH2
propanamine
Functional Groups
Amino Acids
Element Grouping:
Naming:
Example:
H X
H N C
H
O
C OH
TOO complicated
Functional Groups
Esters
O
C O
Element Grouping:
Naming: -name ends in
–oate
O
Example:
HC
O
CH2 CH2 CH3
propyl methanoate
Functional Groups
Amide
O
C NH2
Element Grouping:
Naming: -name ends in
Example:
H
–amide
O
C NH2
methanamide
Drawing Side Chains
CH3
2,2-dimethyloctane
CH3CH2CH2CH2CH2CH2-C-CH3
CH3
1,3-dimethylcyclopentane
H
H3C
H
C
CH3
C H
H C
H C C H
H H
CH2CH3
CH2CHCH2CH2CH2-C-CH2
CH3CH2CH2
6-ethyl-5-propyl-7-methyl-1-heptene
CH3
BELL RINGER
Name the
hydrocarbon
H
H O
H
H
H C–C–C–O–C–C H
H H
H H
ethyl propanoate
Isomers
Structural Isomers
CH3
CH3 CH CH3
CH3 CH2 CH2 CH3
Butane (C4H10)
2-methylpropane (C4H10)
CH2 CH CH2 CH3
CH3 CH CH CH3
1-butene
CH3
CH2 C
CH3
2-methylpropene
2-butene
CH2 CH2
CH2
CH2 CH
CH2 CH2
CH3
cyclobutane methylcyclopropane
Structural Isomers
H OH H
H C C
H H
H H
C H
H C C
H
H H
2-propanol
OH
C H
H
1-propanol
H H
H C C
H H
H
O C H
H
ethyl-methyether
Covalent Molecules Lab
BELL RINGER
Draw and name an isomer
of butanal.
Generally organic reactions occur at a
slower rate  covalent bonds
Many reactions require a catalyst to
lower the activation energy
Types of Reactions
Addition
Reactants: -alkene or alkyne
Produces:
-a double halogenated halocarbon
Example:
H H
H –C=C– H
Special Info:
H H
+
F2
 H –C–C– H
F F
-only occurs with unsaturated hydrocarbons
-results in 2 atoms added
Special type of Addition
“Hydrogenation”
H H H H
H H H H
H–C–C–C=C–H
+ H2
H–C–C–C–C–H
H H H H
H H
Helps turn oils into margarine
Types of Reactions
Substitution
Reactants: saturated hydrocarbon and halogen
Produces:
-a single halogenated halocarbon
Example:
H H H H
H H H H
H–C–C–C–C–H +
H H H H
I2
H–C–C–C–C–H
+
HI
H H H I
Special Info: -only occurs with alkanes, can add more
by doing more than one substitution
Types of Reactions
Fermentation
Reactants: -sugar and yeast
Produces:
Alcohol and carbon dioxide
Example:
H OH
yeast
2 H –C–C– H + 2 CO2
H H
Types of Reactions
Esterification
Reactants: -organic acid and an alcohol
Produces:
Ester and water by dehydration synthesis
Example:
H
O
H
H –C – C– OH + HO –C–H
H
H
O
H
H–C–C–O–C–H +
H
H
HOH
Types of Reactions
Esterification - DEMOS
Acetic Acid + Ethanol
(ethanoic acid)
H
Ethyl ethanoate + Water
O
H H
H –C – C– OH + HO –C–C-H
H
H O
H H
H H
H–C–C–O–C–C–H
H
H H
+
HOH Smells Like:
Fruity?
What is the name of the ester
made between the reaction
of pentanol and acetic acid?
H O
H H H H H
H–C–C– OH
+
HO –C–C–C–C–C–H
H
H O
H H H H H
H H H H H
H–C–C– O –C–C–C–C–C–H
H
H H H H H
Pentyl ethanoate
+ HOH
Smells Like:
Banana?
What is the name of the ester
made between the reaction
of methanol and salicylic
acid?
OH
O
+
H
HOCH3
Smells Like:
wintergreen
O
OH
O
Methyl benzoate
(Methyl salicylate)
O
+ H2O
CH3
Types of Reactions
Saponification
Almost the reverse of esterification (hydrolysis)
Reactants: - a fat and a strong base
Produces: Soap(salt of an acid) and glycerol
Example:
Types of Reactions
Combustion (oxidation)
Reactants: -hydrocarbons and oxygen
-hydrocarbons and limited O2
Produces:
CO2 and H2O
CO and H2O
Example: H H H
H –C–C–C– H + 5 O2  3 CO2 + 4 H2O
H H H
Types of Reactions
Polymerization
Reactants: many small molecules
-amino acids, ethylene
Protein, plastics
Produces:
Example:
H
H
200
C=C
C=C
H
H
H
H
H
H
200
BELL RINGER
Draw the structural formula for the
product of joining two alcohols together:
Propyl ethyl ether
BELL RINGER
Draw the structural formula for the
product of joining two alcohols together:
Propyl ethyl ether
H
H H
H
H
H C–C–C–O–C–C H
H
H
H
H
H
Some additional info
Solubility
Hydrocarbons
are non-polar
Alcohols and
organic acids
are polar
=
Soluble in water
Some additional info
MP & BP
The presence of H bonds increases strength of IMF’s
Alcohols and organic acids
STRONG H Bonds
Amines
weaker
H Bonds
Some additional info
Saturated vs. unsaturated
with respect to Hydrogen's
SATURATED 
UNSATURATED 
Alkanes only
Alkenes or Alkynes
Aka ‘trans fats’  from hydrogenation
‘Cis’ fat
‘Trans’ fat
Fractional Distillation
Further purification – done by cracking and polymerization
Cracking
Chemical breakdown of more complex molecules
into smaller ones
H. Fractional Distillation
Lighter hydrocarbons have lower melting points
CH4 C2H8 Gases at room temperature
Liquid at room temperature
C8H18
Petroleum = mixture of all different hydrocarbons
Heat mixture slowly.
The different hydrocarbons are boiled to a gas and allowed to rise
As they rise, they cool off until they become liquids
Heavier hydrocarbons will not rise as high before they become
liquids
Lightest hydrocarbons will rise the highest
Bell Ringer
Organic Reaction Review
Compound formed
Organic Reaction
4
Ethanol
1. Esterification
2
Glycerol
2. Saponification
5
Fluoroethane
3. Polymerization
3
Polyethylene
4. Fermentation
6
Dichloropropane
5. Substitution
1
Methyl ethanoate
6. Addition
Examples - Perform the following reactions, identify each as
addition or substitution, and draw the products
A.
B.
H H H
| | |
H--C--C--C--H
| | |
H H H
H H
H
| |
|
H--C--C==C--C--H
|
| |
H
H H
+ Cl2
+ Br2
H H H
| | |
H--C--C--C--H
| | |
Cl H H
+ HCl
Substitution
reaction
Cl H Br H
| | | |
H--C--C--C--C--H
| | | |
H Br H H
H H Br H
| | | |
+ Cl2
H--C--C--C--C--H
| | | |
H Br H H addition
reaction
C.
D.
H
|
H-- C  C--C--H
|
H
H--C C--H
+ F2
+ 2 I2
H
H
\
|
C == C--C--H
/
| |
F
F H
+ HCl
addition
reaction
Notice the cis!
I I
| |
H--C--C--H
| |
I I
2 addition
reactions
Substitution
reaction
Examples - Write out the products of the esterification, then
write the molecular formula of the ester
O
||
H--C--OH
H H H H
| |
| |
HO--C--C--C--C--H
| |
| |
H H H H
O
H H H H
||
| |
| |
H--C-- O--C--C--C--C--H
| |
| |
H H H H
+ H2 O
Butyl methanoate
O H
|| |
HO--C--C--H
|
H
H
H H O
| |
|
H--C--C--C--H
| |
|
H H H
H O
H H H
| ||
| |
|
H--C--C--O--C--C--C--H
|
| |
|
H
H H H
Propyl ethanoate