Organic Chemistry Study of carbon based molecules

Bonding Covalent (share valence e-) All Nonmetals Made of carbon, hydrogen and other nonmetals like sulfur, oxygen, nitrogen etc.

Carbon Based Molecules Carbon Atoms Form the “Backbone” Carbon has 4 valence and need 4 more ALWAYS form 4 bonds Bonds can be single, double or triple Due to variety and number of bonds carbon can form you can have an enormous number of combinations

Properties of Organic Compounds

Melting Point Temp. Relatively Low MP (compared to ionic, metallic) MP depends on strength of IMF Non-polar molecules: (Lowest MP) only have VDW attractions (weak) Polar molecules: (Slightly Higher MP) Dipole-dipole attractions or H-bonding Molecules held together more

Solubility Polar molecules: soluble in polar solvents like water Nonpolar molecules: soluble in nonpolar solvents like hexane Look for: Symmetry = nonpolar Symmetry = nonpolar Assymmetry = polar Assymmetry = polar

Conductivity in Solution Organic Molecules usually DO NOT ionize don’t conduct in solution NONELECTROLYTES Important Exception:ORGANIC ACIDS Ex: CH 3 COOH

In Addition Organic Molecules: Undergo combustion in the presence of oxygen Slow rates of reaction due to complexity of bonds (often catalyst needed) Breakdown/decompose at low temperature compared to other compounds

Formula Writing and Drawing Molecules

Types of Formulas Molecular Molecular Empirical Empirical Structural Structural Condensed Structural Condensed Structural

Organic Prefixes (Table P) MethEthPropButPentHexHeptOctNonDec Indicate how many carbon atoms are in the entire molecule You will only see molecules with a max of 10 carbons

Homologous Series of Hydrocarbons (Table Q) Have unique general “formula” Each member of the series differs by one carbon and a certain # of hydrogen

Alkanes General Formula:C n H 2n+2 All single bonds between carbon atoms Name ends in “ane” SATURATED hydrocarbons (holding as many hydrogen atoms as possible)

Alkenes General Formula:C n H 2n One double carbon to carbon bond *Address needed for bond location Name ends in “ene” UNSATURATED hydrocarbons (not totally filled with hydrogen)

Alkynes General Formula: C n H 2n-2 One triple carbon to carbon bond *Address needed for bond location Name ends in “yne” UNSATURATED hydrocarbons (not totally filled with hydrogen)

dienes, diynes etc… Have multiple double or triple bonds. Have multiple double or triple bonds. Give the address for each multiple bond. Give the address for each multiple bond. End of name becomes “-diene…or –triene” End of name becomes “-diene…or –triene” Use prefix “di/tri/tetra/penta” etc…if more than one of the same thing on the chain. Use prefix “di/tri/tetra/penta” etc…if more than one of the same thing on the chain.

Branching Hydrocarbons Have hydrocarbon “branches” off the main carbon chain. Have hydrocarbon “branches” off the main carbon chain. Called “alkyl” groups Called “alkyl” groups

Naming Branched Hydrocarbons Find longest continuous carbon chain and name it (parent chain) Find longest continuous carbon chain and name it (parent chain) Find address of each branch Find address of each branch Count carbons in each branch Count carbons in each branch Name branches using prefix ending in “yl” Name branches using prefix ending in “yl” Ex: 2 carbon branch would be an “ethyl” branch. Ex: 2 carbon branch would be an “ethyl” branch. Note: If more than one of the same type of branch use “di”, “tri”, “tetra” etc…instead of repeating the name

Isomers Same molecular formulas, but different structural formulas. Same molecular formulas, but different structural formulas. Atoms in the molecule have a different arrangement. Atoms in the molecule have a different arrangement. The more atoms the larger the number of possible isomers The more atoms the larger the number of possible isomers

Cyclical Hydrocarbons Form rings Form rings Start with “cyclo-” Start with “cyclo-”

Benzene Series Benzene Series: 6 carbon ring with alternating double bonds. Electrons in double bonds “resonate” between bond sites giving more strength to all the bonds Branches and functional groups are often attached to the ring Ortho/Meta/Para locations

Organic Functional Groups Reference Table R

Halides Contain one or more halogen atoms. Contain one or more halogen atoms. Fluoro / chloro / bromo / iodo prefix Fluoro / chloro / bromo / iodo prefix Use address Use address Use di, tri, tetra if more than one of same Use di, tri, tetra if more than one of same

Alcohols Have one or more “Hydroxyl” groups (-OH) Have one or more “Hydroxyl” groups (-OH) Use address Name ends in “-ol” If more than one (–OH), name ends in “diol”, or “triol” Important Example: Glycerol or 1, 2, 3 propantriol Important Example: Glycerol or 1, 2, 3 propantriol

Types of Alcohols Primary Primary Secondary Secondary Tertiary Tertiary

Aldehydes Carbon double bonded to oxygen at end Carbon double bonded to oxygen at end of a carbon chain (“carbonyl” group) ADDRESS NOT NEEDED (always at end!) ADDRESS NOT NEEDED (always at end!) End in “–al” End in “–al”

Ketones Carbon double bonded to oxygen in middle of a carbon chain (“carbonyl” group) Carbon double bonded to oxygen in middle of a carbon chain (“carbonyl” group) Use address Use address End in “-one” End in “-one”

Ethers Oxygen atom within carbon chain Oxygen atom within carbon chain Count carbon atoms on either side of oxygen and name them like “alkyl” branches. Count carbon atoms on either side of oxygen and name them like “alkyl” branches. “Butterflies” with belly buttons “Butterflies” with belly buttons

Organic Acids At the end of the carbon chain is a “carboxyl” group containing two oxygen atoms. At the end of the carbon chain is a “carboxyl” group containing two oxygen atoms. ADDRESS NOT NEEDED (always at end!) ADDRESS NOT NEEDED (always at end!) End in “-oic acid” End in “-oic acid” Has an acidic hydrogen that ionizes so these are ELECTROLYTES Has an acidic hydrogen that ionizes so these are ELECTROLYTES

Esters Within the chain, there is an oxygen atom that is next to a carbon double bonded to oxygen Within the chain, there is an oxygen atom that is next to a carbon double bonded to oxygen Use oxygen inside of chain as middle point. (Sorta like an “ether” belly button) Use oxygen inside of chain as middle point. (Sorta like an “ether” belly button) Name both sides around the oxygen atom Side with carbon “Alkyl” branch, ends in “yl” Side with carbon “Alkyl” branch, ends in “yl” Side with the double bonded oxygen ends in “oate” Side with the double bonded oxygen ends in “oate”

Amines Have an “amine” group containing nitrogen. Have an “amine” group containing nitrogen. Use address Use address Ends in “-amine” Ends in “-amine” Important Example: Amino Acid Important Example: Amino Acid

Amides Also have a nitrogen atom, but it is next to a carbon double bonded to oxygen. Also have a nitrogen atom, but it is next to a carbon double bonded to oxygen. End in “amide”. End in “amide”.

Organic Reactions

Combustion Burning or oxidation of a hydrocarbon. Burning or oxidation of a hydrocarbon. Needs O 2 Needs O 2 Produces CO 2 and H 2 O Produces CO 2 and H 2 O Always EXOTHERMIC Always EXOTHERMIC If not enough O 2 present, you can get “incomplete” combustion resulting in carbon monoxide (CO) and soot (C). If not enough O 2 present, you can get “incomplete” combustion resulting in carbon monoxide (CO) and soot (C).

Fermentation Makes ALCOHOL!!! Makes ALCOHOL!!! Sugar is metabolized by yeast enzymes to make ethanol and CO 2 Sugar is metabolized by yeast enzymes to make ethanol and CO 2

Substitution Happens with ALKANES Happens with ALKANES One atom comes off and is “substituted” for another atom. One atom comes off and is “substituted” for another atom. Results in TWO products Results in TWO products Ex: Halogen Substitution Ex: Halogen Substitution

Addition Happens with ALKENES and ALKYNES. Happens with ALKENES and ALKYNES. A double or triple bond “opens up” A double or triple bond “opens up” Two atoms “add on” for each broken bond Two atoms “add on” for each broken bond Results in ONE product. Results in ONE product. Ex: Ex: Halogen Addition Halogen Addition Hydrogenation Hydrogenation

Polymerization Joining together of many individual “monomers” to make a “polymer”. Ex: Synthetic Polymers Ex: Synthetic Polymers Nylon Nylon Rayon Rayon Polyethelene Polyethelene Polypropylene Polypropylene Polystyrene (styrofoam) Polystyrene (styrofoam) Polyester Polyester Ex: Natural Polymers Ex: Natural Polymers DNA/RNA DNA/RNA Starch, Cellulose Starch, Cellulose Proteins Proteins

Types of Polymerization Condensation Polymerization Condensation Polymerization Remove water to join monomers Remove water to join monomers Ex: Amino Acids joining to make “peptide” bonds Ex: Amino Acids joining to make “peptide” bonds Addition Polymerization Addition Polymerization Open up double/triple bonds to join monomers Open up double/triple bonds to join monomers Happens to alkenes/alkynes Happens to alkenes/alkynes

Cracking Breaking of long hydrocarbon chains into smaller ones. Breaking of long hydrocarbon chains into smaller ones. Often used on long chain hydrocarbons found in petroleum to make them into more usable fuels. Often used on long chain hydrocarbons found in petroleum to make them into more usable fuels. Usually involves a catalyst Usually involves a catalyst

Fractional Distillation Separation of a petroleum mixture by differences in Boiling Point temperature. Separation of a petroleum mixture by differences in Boiling Point temperature. Most compounds in petroleum are non- polar hydrocarbons. Most compounds in petroleum are non- polar hydrocarbons. Larger chains = stronger VDW = higher BP Smaller chains = weaker VDW = lower BP

***Esterification*** Dehydration synthesis (water is removed to join molecules) Dehydration synthesis (water is removed to join molecules) Alcohol + Organic Acid Ester + Water Ester molecules often have nice odors Ester molecules often have nice odors Fats are a type of ester made of glycerol and 3 fatty acid chains Fats are a type of ester made of glycerol and 3 fatty acid chains

Saponification (Making Soap) Soap molecules are long molecules that are nonpolar at one end and polar at the other end. Soap molecules are long molecules that are nonpolar at one end and polar at the other end. Can bring oil and water together Can bring oil and water together Ester + Base Soap + Glycerol