Organic Chemistry Flashcards
Properties of Organic Molecules
Weak IMF (London Dispersion), therefore…
- Low melting point and boiling point
- High Vapor Pressure (turn to gas easily)
-Volatile & Combustible
(all based on length of the carbon chain)
Slow to chemically react
- Ionic compounds in solution reacts faster
Major Natural Resource.
- (Natural Oil, Petroleum, Coal, Natural gas)
Organic Properties of Hydrocarbons
- Covalent Bonds - Carbon and Hydrogen ONLY
- Symmetrical Non-Polar Molecules
- Low IMF (London Dispersion Force)
- Soluble in non-polar solvents and insoluble in H2O
- Nonelectrolytes (No ions present to dissociate)
HYDROCARBON BOND TYPES
Compounds composed entirely of carbon and hydrogen atoms bonded to each other by covalent bonds.
- Alkanes (single bond C-C)
- Alkenes (double bond C=C)
- Alkynes (triple bond C C)
How many bonds can a carbon atom make?
Each carbon atom is able to form four covalent bonds (has 4 valence electrons).
single bonds (share 2 electrons)
double bonds (share 4 electrons)
triple bonds (share 6 electrons)
Hydrocarbons can form
Aliphatic Linear Chains
Aromatic Ring Structures
Aliphatic Linear Chains can be classified further…
3) Saturated Hydrocarbons
4) Unsaturated Hydrocarbons
SATURATED
Hydrocarbon that contains only single bonds - every carbon is saturated with 4 possible bonds.
Always Alkanes.
UNSATURATED
Hydrocarbon that contains one or more double or triple bonds - not all carbons are saturated with single bonds.
Always Alkene and Alkyne
HOMOLOGOUS SERIES
Groups of organic compounds that have similar properties and related structures
Formulas will be multiples of each other
ALKANE SERIES
Group of hydrocarbons which contain carbon atoms linked by single bonds
Alkanes are saturated compounds
Naming: prefixes are used to relate the
# of carbons in the compound
ALKANE SERIES
All end in suffix “–ane”
General Formula (CnH2n+2) (Table Q)
As the number of carbons increases the boiling point increases.
ISOMERS
Compounds that have the same molecular formula, but different structural formulas
What does isomerism start with (alkane series)?
Isomerism begins with butane, C4H10
normal (n) butane
(n-butane)
isobutane
NAMING ISOMERS
KEY IDEA: longest continuous chain of carbon atoms
Number the longest carbon chain so that the attached group gets the lowest possible #
Branch is named using the # of Carbons prefix, followed by the suffix “-yl”
Name ends in longest carbon chain name
Naming Isomers - HALOGENS
If a halogen is attached to the Carbon chain
(ex: -F fluoro, -Br bromo, -Cl chloro)
Number the carbon atom the halogen is attached to
(ex: 1-chlorobutane)
Naming Isomers - ALKENES
Isomers are named for position of
the double bond
1-butene, C4H8
2-butene, C4H8
Naming Isomers - ALKYNES
Named for the position of the triple bond
1-butyne, C4H6
2-butyne, C4H6
Functional Groups
Atoms or groups of atoms that give certain characteristics to an organic molecule
(determine how a molecule will react)
HALIDES
Compounds in which a halogen atom (F, Cl, Br, or I) replaces a hydrogen one from an alkane
Chloromethane, CH3Cl
Bromoethane, CH3CH2Br
Use a number to note the location of the halogen on the carbon chain
ALCOHOLS
Contain the functional group: -OH
Example: R-OH
“R” represents some carbon chain
Naming: named for the parent alkane chain, replace last e with –ol
CH3OH, Methanol
CH3CH2OH, Ethanol
ETHERS
Contains functional group -O-
General formula: R-O-R’
Naming: right side of the -O- is named first, then the left side of the -O- is named
CH3OCH3 = methyl methyl ether
CH3CH2OCH3 = methyl ethyl ether
ORGANIC (CARBOXYLIC) ACIDS
Contain the functional group: -COOH
General Formula: R-COOH
Naming: name for # of carbons use alkane name drop –e and add “-oic acid”
HCOOH, methanoic acid
CH3COOH, ethanoic acid (vinegar)
AMINES (PRODUCTS OF AMMONIA)
Functional group: -NH2
General Formula: R-NH2
Naming: name the alkane group to which
the amine is attached
drop the –e ending and add -amine
CH3NH2 methanamine
CH3CH2NH2 ethanamine
ALDEHYDES
Contains the functional group: R-CHO
Can have fragrant (unpleasant) odors
Naming: use alkane name for the carbon chain (including carbon attached to the oxygen)
drop –e and add –al
COH2 = methanal
CH3COH = ethanal
KETONES
Contain the functional group: R-C=O is found on an interior carbon atom that is attached to two other carbon atoms
Naming: use alkane name for longest carbon chain, use number where Ketone is located.
drop –e ending, add –one
CH3COCH3 = propanone (acetone)
CH3CH2COCH3 = 2-Butanone
AMIDES
Contain the functional group: RCONH2
Naming: name the longest carbon chain as you would an alkane
drop the –e and add -amide
CH3CONH2 ethanamide
CH3CH2CONH2 propanamide
ESTERS
Contain the functional group: R-COOR’
Used in perfumes because of their aromas
Naming: names are derived from the alcohol and the Organic acid from which it is formed
portion from the alcohol comes 1st (this is R’)
portion from the acid come 2nd using the alkane name, dropping the -e and adding –oate
CH3COOCH2CH3 ethyl ethanoate
AMINO ACIDS
Organic molecules containing the Carboxyl group (R-COOH), making it an acid, and an amine group (R-NH2) making it an amino molecule. There are many different kinds of Amino Acids, however it is not necessary that you memorize them. Amino Acids can link together like polymers(polymers of biomolecules are called polypeptides), the NH2 of one will attach to the -OH of the other molecule
Contain both the amine and the organic acid functional group
RING STRUCTURES
Some carbon chains can be linked to themselves in a ring
Benzene C6H6
Tend to be called aromatic rings, because they often produce an aroma (often unpleasant and flammable)
Combustion
When sufficient oxygen is present, hydrocarbons will burn to produce carbon dioxide and water
C3H8 + 5O2 → 3CO2 + 4H2O
When the supply of oxygen is limited, carbon and carbon monoxide will also be produced
Substitution
Replacement of one kind of atom by another atom or group of atoms
Saturated hydrocarbons can be replaced by halogens (F, Cl, Br, I), known as halogenation substitution.
C2H4 + Cl2 → C2H3Cl + HCl
Notice how only 1 Chlorine binds to the alkane chain, and the substituted hydrogen atom bonds to the remaining chlorine atom.
Addition Reactions
The addition of one or more atoms or group of atoms to a double or triple bond (unsaturated) hydrocarbon chain, making a saturated hydrocarbon.
Will break the double/triple bond
Looks similar to a synthesis reaction
Addition reactions have only one product
(saturated hydrocarbon)
Halogenation Addition
The addition of a halogen
C2H4 + Cl2 → C2H4Cl2
Addition reactions have only one product
(saturated hydrocarbon)
Converts Alkene (double bond) Hydrocarbons into Alkane (single bond) hydrocarbons.
Notice addition sticks BOTH ATOMS to the hydrocarbon chain
Hydrogenation
Addition of hydrogen
C2H4 + H2 → C2H6
Addition reactions have only one product
(saturated hydrocarbon)
Converts Alkene (double bond) Hydrocarbons into Alkane (single bond) hydrocarbons.
Notice addition sticks BOTH ATOMS to the hydrocarbon chain
Esterification
Reaction between an organic acid and an alcohol to produce water and an ester
CH3COOH + CH3CH2OH → H2O + CH3COOCH2CH3
Saponification
The reaction between a fat and a strong base produces soap (salt of an organic acid) and glycerol
Fermentation
enzyme from yeast acts as a catalyst to turn sugars into alcohol
C6H12O6 → 2C2H5OH + 2CO2
Polymers
Organic compounds made up of chains of repeating smaller units bonded together
Monomers
Monomers: the individual units that make up a polymer
Natural vs Synthetic Polymer Examples
Natural polymers: starches, cellulose, proteins
synthetic: polyethylene, polystyrene, rubber, plastic
Condensation Polymerization
The bonding of monomers by dehydration (removal of H2O)
Addition Polymerization
A polymer which is formed by an addition reaction, where many monomers bond together via rearrangement of bonds without the loss of any atom or molecule.
Benzene Series – Unsaturated Rings
Know the first two!! Gen. formula = CnH2n-6
Benzene: C6H6
Toluene: C7H8
Naming Alkane Isomers
Find the longest main chain of C-C bonds.
Find all side chains and circle them.
Number the main chain carbons (1, 2, 3, 4,….)
in both directions.
The lesser numbers are using the naming process.
1) Longest Chain:
4 carbons long
Side Chains?
None
IUPAC Name?
2) Longest Chain:
3 carbons long
Side Chains?
1 (2nd C → methyl)
IUPAC Name?
1) Butane
2) 2-methyl propane
1) Longest Chain:
5 carbons long
Side Chains?
None
IUPAC Name?
2) Longest Chain:
4 carbons long
Side Chains?
1 (2nd C → methyl)
IUPAC Name?
3) Longest Chain:
3 carbons long
Side Chains?
2 (2nd C → dimethyl)
IUPAC Name?
1) Pentane
2) 2-methyl butane
3) 2,2-dimethyl propane
Naming Alcohols
Named for the parent alkane chain, replace last e with –ol
CH3OH, Methanol
CH3CH2OH, Ethanol
Use “-diol” or “-triol” to represent 2 or 3 alcohol groups on a hydrocarbon chain.
Naming Ethers
1) Hydrocarbon on left side of the -O- is named first
2) Hydrocarbon on right side of the -O- is named
CH3OCH3 = methyl methyl ether or dimethyl ether.
CH3CH2OCH3 = ethyl methyl ether
Organic Acids
Weak Organic Acids (safe around metals) (no ions)
Flavoring or preservatives, preventing the growth of bacteria and pathogens in food.
Lactic Acid (Muscles + Cellular Respiration)
Citric Acid (citrus fruits + preservation)
Naming Organic Acids
- # Carbons in Hydrocarbon chain
- drop –e and add “-oic acid”
Methanoic Acid (CHOOH), Butanoic Acid (CH3CH2CH2COOH)
- drop –e and add “-oic acid”
Naming Amines
Name the Hydrocarbon Chain
Drop the –e ending and add -amine
CH3NH2 methanamine
CH3CH2NH2 ethanamine
Naming ALDEHYDES
Name the Hydrocarbon Chain
Drop –e and add –al
COH2 methanal
CH3COH ethanal
Naming Ketones
Count Hydrocarbon Chain and determine Carbon #
Drop –e ending, add –one
CH3COCH3 propanone (acetone)
CH3CH2COCH3 2-Butanone
Ketone Attachment
Ketone Groups can only attached themselves to Hydrocarbons with a Carbon chain equal or greater than 3 in length.
Ketone group must be identified in Hydrocarbons longer than 4 carbons in length.
Naming Amides
Name the Hydrocarbon Chain
Drop the –e and add -amide
CH3CONH2 ethanamide
CH3CH2CONH2 propanamide
Naming Esters
Find Functional Group
Right side hydrocarbon side chain named first
Left side Hydrocarbon named second
End second name in “-oate”
CH3COOCH2CH3 ethyl ethanoate
Cyclohexane
C6H12
(Aliphatic Linear Ring)
Saturated
Etherification
Reaction between two alcohol groups (along with an acid, like H2SO4) to create an ester molecule (r-O-r’
Estherification
Reaction between an organic acid and an alcohol to produce water and an ester
CH3COOH + CH3CH2OH → H2O + CH3COOCH2CH3
