ORGANIC CHEMISTRY

ORGANIC CHEMISTRY The study of Carbon.

Carbon is in all living things.

Carbon is an extremely versatile elements and can bond with other carbon atom to make chains, rings, and vast networks creating countless numbers of compounds.

CARBON BONDING A Lewis dot structure displays carbon

having only 2 unpaired electrons in its ground state.

When Carbon bonds however, the paired electron can split apart and occupy separate orbitals, allowing carbon to form four covalent bonds.

Carbon in its ground state

Carbon in its bonded state

CARBON BONDING Carbon can share its four unpaired electrons

to make multiple covalent bonds when forming a chain.

Covalent Bond = bond formed by the sharing of electrons between two atoms.

Single Covalent Bonds – sharing of one pair of electrons between two carbon atoms. Represented by a single line.

Double Covalent Bonds – sharing of two pairs of electrons. Represented by a double line.

Triple Covalent Bonds – sharing of three pairs of electrons. Represented by a triple line.

CARBON BONDING Carbon is able to form many different compounds

due to its unique bonding capabilities.

PROPERTIES OF ORGANIC COMPOUNDSDue to the nature of covalent bonds organics

generally possess the following properties. Low Melting Points Low Boiling Points Poor Conductors of Electricity

Non-Electrolytes Poor conductors of Heat Non-polar

“Like Dissolves like” Slow Reaction Rates.

Organic compounds that contain only single bonds are called Saturated.

Organic compounds with one or more double or triple bonds are called Unsaturated.

STRUCTURAL FORMULAS Attempt to display the what the organic

compound looks like.Number of atoms Identity of atomsBondsGeneral Shape

Example: Molecular Formula C3H8

Structural Formula

Condensed Formula; CH3CH2CH3

HYDROCARBONS A homologous series of compounds that

contain only hydrogen and carbon. Homologous Series – a group of related compounds in

which each member differs from the one before it by the same additional unit.

Form the backbone of most organic substances.

Categorized by the covalent bonds they possess. Alkanes Alkenes Alkynes

ALKANES Hydrocarbon series that possess only

single covalent bonds between carbons. Tend to release energy when burned. Examples:

Homologous series (CH2) Suffix: -ane General Formula: CnH2n+2

Methane

Ethane Propane

ALKENES Hydrocarbon series where at least one double

covalent bond is present between two carbons. Used to make organic substances such as polypropyene. Examples:

Homologous Series (CH2) Suffix: -ene General Formula CnH2n

Ethene

Propene

Butene

ALKYNES Hydrocarbon series where at least one triple

covalent bond is present between two carbons. Used in welding. Examples:

Homologous Series (CH2) Suffix: -yne General Formula CnH2n-2

Ethyne

Propyne

Butyne

ISOMERS Compounds that possess the same molecular

formula but have more than one structural formula. Example: C4H10

Despite having the same structural formula, isomer will exhibit very different chemical and physical properties.

The number of possible isomers increases as the number of carbon atoms increases.

Butane

Methyl Propane

NAMING ORGANIC COMPOUNDS1. Find the longest carbon chain which contains the

functional group or multiple bond if present and name it (using the correct ending).

2. Number the longest chain (left to right or right to left) so that the functional group/multiple bond/longest side chain (branch) is on the lowest numbered carbon possible.

3. Name each side group but change the ending to -yl. (Alkyl groups)

4. Use a prefix di-, tri-, tetra-, etc. to denote how many side groups of each length are present.

5. Before naming the side group give the number of the carbon to which the side group is attached.

6. Arrange the side groups in alphabetical order ignoring the prefixes di-,tri-, etc.

NAMING ORGANIC COMPOUNDS Name this hydrocarbon…

NAMING ORGANIC COMPOUNDS1. Find the longest carbon chain which contains the

functional group or multiple bond if present and name it (using the correct ending).

NAMING ORGANIC COMPOUNDS2. Number the longest chain (left to right or right to

left) so that the multiple bond/functional group/longest side chain (branch) is on the lowest numbered carbon possible.

The number of carbons determines the name of the parent chain.6 carbons = hex = hexene

NAMING ORGANIC COMPOUNDS3. Name each side group but change the ending to -

yl. (Alkyl groups)

1 Carbon = methane,side group(alkyl group) = methyl

NAMING ORGANIC COMPOUNDS4. Use a prefix di-, tri-, tetra-, etc. to denote how

many side groups of each length are present.

Only 1 methyl side group present.

NAMING ORGANIC COMPOUNDS5. Before naming the side group give the number of

the carbon to which the side group is attached.

2-methyl

NAMING ORGANIC COMPOUNDS6. Arrange the side groups in alphabetical order

ignoring the prefixes di-,tri-, etc.

2-methyl hexene

Condensed Formula: CH3CH2CH2CH2CH(CH3)CH3

FUNCTIONAL GROUPS Atoms or groups of atoms that attach to

hydrocarbon chains. Create whole new compounds each with their own

distinct chemical and physical properties. Halides Alcohols Adehydes Ketones Ethers Organic Acids (COOH) Amines Amino Acids Amides

HALIDES One of the Halogens (Group 17) is

attached to the hydrocarbon chain, replacing a hydrogen.Organic Halide(Halocarbon)

Halides are named for the halogen present on the hydrocarbon chain with a number designating which carbon it is on.F = flouro, Cl = chloro, Br = bromo, I = iodo

Chloromethane

CH3Cl

2,2,3-tricholorbutaneCH3CCl2CCHClCH3

ALCOHOLS Compounds in which one or more hydrogen

atoms on a hydrocarbon chain are replaced by an –OH group (Hydroxyl Group). Does not form OH- ions in water. Alcohols are non-electrolytes. Alcohols are polar and are soluble in polar

solvents such as water. Suffix: -ol

Classification of alcohols Primary Secondary Tertiary

CLASSIFICATION OF ALCOHOLS Primary Alcohol – has the hydroxyl

group(OH) attached to a primary carbon at the end of the chain.Represented by R-OH or R-CH2OH

1-butanol

CLASSIFICATION OF ALCOHOLS Secondary alcohol – has a hydroxyl

group (OH) attached to a secondary carbon.Represented by R-CH(OH)-R’

2-butanol

CLASSIFICATION OF ALCOHOLS Tertiary Alcohols – have a hydroxyl

group (OH) attached to a tertiary carbon atom.Represented by R1R2R3COH

2-methy, 2-propanol

POLY-HYDROXY COMPOUNDS Some organic compounds contain more

than on hydroxyl group.Monohydroxy – an alcohol with one –OH

group. Suffix; -ol

Dihydroxy – an alcohol with two -OH groups. Suffix; -diol

Trihydroxy – an alcohol with three –OH groups. Suffix; -triol

1,2-ethanediol

1,2,3-propanetriol

ALDEHYDES Hydrocarbons that contain a carbonyl

group (-C=O) on a primary (end) carbon.Suffix; -al

Methanal Propanal

KETONES Hydrocarbons that contain a carbonyl

group (-C=O) on a secondary carbon (a carbon that is attached to two other carbons).Suffix; -one

Propanone

ETHERS Two carbons chains joined together by

an oxygen atom between them.R-O-R’Suffix; -yl ether

dimethyl ether

ethylmethyl ether

ORGANIC ACIDS Hydrocarbon chain with a carboxyl (-

COOH) group attached.R-COOHSuffix; -oic acid

methanoic Acid ethanoic Acid

ESTERS Organic compounds with a generalized

formula of;R-CO-OR’ (where R’ is an alcohol and R is an

acid)Suffix; -yl (alcohol part)

-oate (acid part)

Ethyl ethanoate

AMINES Derivatives of ammonia.

Alkyl groups attach to the Nitrogen in place of a hydrogen on the ammonia (NH3) molecule.

suffix; -amine

pent-2-amine

AMINO ACIDS Contain a carboxyl group as well as an

amine group.Building blocks of proteins.10 essential amino acids.

Alanine

AMIDES Compound formed by the combination

of two amino acids during a condensation reaction.

ORGANIC REACTIONS1. Combustion Reactions

Hydrocarbons burn in the presence of sufficient oxygen to produce water and carbon dioxide.C3H8(g) + 5O2(g) 3CO2(g) + 4H2O(g)

Complete Combustion

If there is not enough oxygen present water and carbon monoxide (CO) will be produced instead.2C3H8(g) + 7O2(g) 6CO2(g) + 8H2O(g)

Incomplete Combustion

ORGANIC REACTIONS2. Substitution

Involves the replacement of one or more hydrogens in saturated hydrocarbon with another atom or group.

C2H6 + Cl2 C2H5Cl + HCl3. Addition

Involve adding one or atoms at a double or triple bond.

C2H4 + Cl2 C2H4Cl2 Unsaturated hydrocarbons can also react with

hydrogen by addition reactions producing a saturated hydrocarbon.

C2H4 + H2 C2H6

ORGANIC REACTIONS4. Esterification

Reaction between an organic acid and an alcohol to produce an ester plus water.

ethanoicAcid

ethanol ethylethanoate

water

ORGANIC REACTIONS5. Saponification

an ester reacts with an inorganic base to produce an alcohol and soap.

ORGANIC REACTIONS6. Fermentation

Six Carbon chains of sugar are broken down into carbon dioxide and two carbon fragments of alcohol.

C6H12O6 2C2H5OH + 2CO2

7. Polymerization Polymers – long hydrocarbon chains made up of smaller

covalently bonded chains called monomers. Ex: proteins, starches, cellulose, synthetic plastics

a. Addition Polymerization – the joining of monomers of unsaturated compounds.

4C2H2 (C2H2)4

nC2H2 (C2H2)nb. Condensation Polymerization – removal of water from

hydroxyl groups and the joining of monomers by an ether or ester linkage.