CHAPTER ONE- ORGANIC COMPOUNDS
Functional Groups- a group of atoms within a molecule that give certain characteristics to that molecule.
H
H
H
C
C
H
H
H
H
H
C
Double Bond; bond is not as
strong; reactive.
C
H
H
Single Bond; Bond is very
strong; unactractive.
H
C
C
H
Triple Bond; Bond is not as
strong; reactive.
C-O
Polar Bonds increases intermolecular attractions, increases melting and boiling points
C-N
Polar Bonds increases intermolecular attractions, increases melting and boiling points
C-Halo
Polar Bonds increases intermolecular attractions, increases melting and boiling points
C-OH
Allow for Hydrogen bonding, increases solubility in polar substances “likes dissolves likes”
C-NH
Allow for Hydrogen bonding, increases solubility in polar substances “likes dissolves likes”
IUPAC Naming
1.
2.
3.
4.
Your Base name is determined by the number of your longest chain of carbons.
Numbering starts at the end closest to a side chain.
Name and give the location of each branch.
Multiple side chains get named in alphabetical order.
Organic NomenclatureNumber Of Carbons
Prefix
1
Meth-
2
Eth-
3
Prop-
4
But-
5
Pent-
6
Hex-
7
Hept-
8
Oct-
9
Non-
10
Dec-
Branches (Substituents)
Methyl
A
Ethyl
A
CH3
n-propyl
A
H3C
Isopropyl
CH2
CH2
CH3
CH3
CH2
CH3
CH
A
n-butyl
CH2
A
CH2
CH3
CH2
CH3
s-butyl
A
HC
CH2 CH3
CH3
Isobutyl
CH
H3C
A
CH2
CH3
t-butyl
A
C
CH3
CH3
Reactions of Alkanes
i)Combustion:
CH4 + O2  H2O + CO2
ii) Substitution:
H
H
H
C
C
H
H
H
+
H
Br Br
Catalyst
H
H
Br
C
C
H
H
H
Reactions of Alkenes and Alkynes
i) Halogenation:
H
H
C
+
C
H
H
Br
H
Br
Br
Br
C
C
H
H
H
ii) Hydrogenation:
H
C
C
H
+
H2
H
H
H
C
C
H
H
H
H
+
HBr
iii) Hydrohalagenation:
H
H
H
C
+
C
H
H
I
H
C
H
I
H
C
C
C
H
H
H
H
H
H
“rich get richer”
iv)Hydration:
H
H
H
C
H
+
C
H
H
H2SO4
H
O
C
H
OH H
C
C
C
H
H
H
H
H
H
Markovnikov’s Rule: The Carbon that has the most Hydrogen already gets the extra Hydrogen “The rich
get richer”
Reactions of Aromatic Hydrocarbons:
i) Substitution:
Cl
CH
HC
CH
HC
CH
CH
+
Cl
Cl
CH
HC
C
HC
CH
CH
Synthesis Pathways:
Important reminder:
Always remember where Markovnikov’s rule will apply.
Ex.
Write a series of equations to illustrate the synthesis of ethyl butanoate from an alkene and an
alcohol.
Solution:
Ethyl Butanoate
Ethanol (alcohol)

Ethane (alkene) + Water
Butanoic Acid (Carboxylic Acid)

Butanal (Aldehyde) + (O)

1-Butanol (alcohol)+ (O)
The Reactions:
1)
H
H
H
H
H
C
C
H
+
CH2
CH2
H
H
H
C
(O)
C
OH
+H
C
H
CH2
H
O
O
H
butan-1-ol
butanal
2)
H
H
H
H
H
C
+
C
H
CH2
OH
CH2
H
C
C
(O)
C
C
O
H
H
H
O
H
butanal
butanoic acid
1)
OH
H2C
CH2
+
ethene
H3C
H2O
CH2
ethanol
Combine the two end products
H
H
OH
H3C
CH2
C
+
C
C
H
H
H
C
CH3
CH2
C
C
H
ethanol
OH
CH2
H
O
CH2
H
O
H
O
ethyl butanoate
H
butanoic acid
ALDEHYDES
Functional Group:
Formaldehyde
C=O (carbonyl groups). Must be at the end
Example:
Naming:
H3C
CH
O
Ethanal
Properties: C=O => Polar, but no H-bonds, Higher bp/mp than parent hydrocarbon lower than alcohol of
the same group (H-bond with alcohol)
Reactions: a) Controlled Oxidation of primary Alcohol
H3C
CH2
OH
+
(O)
H3C
CH
O
b) Hydrogenation
H3C
CH
O
+
H2
H3C
CH2
OH
ETHER
Functional Group:
O A
Example:
Diethylether
A
Naming:
H3C O
CH2CH3
methyl ethyl ether
or methoxyethane *smaller hydrocarbon goes first
Properties:
Bond is Polar, good solvent
Reactions: Condensation with two alcohols:
H3C
OH
+
H3C
H3C
CH3
CH3
+
O
H2O
ORGANIC HALIDES
Functional Group:
Example:
CFC, Teflon, DDT
R-X
Naming:
H
Cl
H
C
C
H
Cl H
1,2-dichloroethane
Properties: Polar molecules have higher mp/bp. Soluble in polar liquids.
Reactions: a) Synthesis
H
H
C
+
C
H
Cl
Cl
H
H
H
Cl
C
C
H
Cl H
1,2-dichloroethane
ethene
b) Elimination:
H3C
CH
CH3
Cl
2-chloropropane
H3C
+
-
HO
hydroxide
CH CH2
prop-1-ene
+ H2O +
Cl
-
ALCOHOLS
Functional Group:
A
OH
Example:
Glycerol
Ethanol
Cholesterol
Naming:
H3C
CH
H3C
OH methanol
OH
H3C
2-propanol
Properties: Polar Molecules (OH) have higher mp/bp. Many alcohols have large chains of carbon at the
end making it a good solvent dissolving polar and non polar substances.
Reactions: a) Combustion
H3C
+
CH CH3
+
H2
O O
O
C
O
HO
b) Synthesis
H3C
acid
+
CH2
H2O
CH CH2
H3C
CH2
CH3
CH
OH
c)
Elimination
H3C
H2SO4
Catalyst
CH3
CH
H3C
CH CH2
+
H2O
OH
KETONES
Functional Group:
Example:
O
Acetone
C
A
A
Naming:
O
O
C
CH2
C
H3C
CH3
H3C
propan-2-one
CH2
CH3
pentan-2-one
Properties:
Carbonyl group makes it similar to aldehydes
Reactions: a) Controlled oxidation with a 2 alcohol
CH3
CH3
+
CH
H3C
(O)
H3C
OH
+
C
O
b) Addition with H2 (Hydrodgenation)
O
H
H
H3C
H
C
C
H
C
+
C
H H
H
CH3
H2
CH
H
HO
CH2
H2O
CARBOXYLIC ACIDS
Functional Group:
O
A
Example:
Methanoic Acid
Citric Acid
ASA- Acetylsalicylic Acid
C
OH
Naming:
OH
CH2
H3C
C
H3C
O
CH2
CH2
OH
H3C
C
HC
Properties:
polar
O
OH
C
OH
C
CH3
O
pentanoic acid
ethanoic acid
CH2
C
HO
O
ethanedioic acid
O
3-methylbutanoic acid
Higher melting and boiling points
O
A
C
OH H-Bonding
Reactions: Controlled oxidation of alcohol to Alde Hyde to Carboxylic Acid:
H
A
OH
H
C
OH
+ (O)
A
C
O
+ H2O + (O)
A
H
ESTERS
Functional Group:
O
C
Example:
Fruit and Flower Fragrances
A
A
O
Naming:
O
C
H3C
CH2
O
CH2CH3
ethyl propanoate
*Alcohol root always first
Properties:
-Not very polar
-Not very acidic
Reactions: a)Condensation Reaction (Esterfication):
OH
HO
CH2 CH3
ethanol
+
O
O
C
C
CH2 CH3
propanoic acid
b) Hydrolysis:
Ester + NaOH Sodium salt of the acid + alcohol
H3C
CH2
O
CH2CH3
ethyl propanoate
C
O
AMINES
Functional Group:
A
N
Example:
Amphetamines
Decomposing
A
A
Naming:
CH3
H
H3C
CH CH2
N
H
H
N
CH2 CH3
H
methylamine or amino methane
2-aminopentane or s-pentylamine
Properties:
-High melting and boiling points because of polar N-C bonding and N-H bonding
Reactions: Reaction with ammonia:
I
NH3
+
ammonia
H3C
H3C
+
CH2
CH2
iodoethane
NH2
H I
hydrogen iodide
ethanamine
AMIDES
Functional Group:
A
A
C
Example:
Protein
NH
O
Naming:
O
H3C
CH2
O
C
NH2
CH2
butanamide
H3C
C
CH2
NH
CH3
N-methylpropanamide
Properties:
-Weak Bases
-Some weak H-bonds (mostly soluble in water)
Reactions: Hydrolysis Reaction:
HO
OH
C
CH2
C
NH2
O
NH2
O
CH2
HO
+
H2N
C
O
CH2
CH2
NH C
O