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 Atoms Form the “Backbone” Carbon has 4 valence and needs 4 more ALWAYS forms 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 Relatively Low MP (compared to ionic, metallic) MP depends on polarity of molecule & strength of IMF Many are Non-polar molecules: (Lowest MP) Weak attractions (VanDerWaals /dispersion forces) Larger NP molecules have higher MP than smaller Some are Polar molecules: (Slightly Higher MP) Can have Dipole-dipole attractions or H-bonding Molecules held together more Stronger IMF

For nonpolars the more atoms in chain the higher the Boiling Point

Properties of Organic Compounds SOLUBILITY: Depends on polarity of molecule (Many org. compounds are nonpolar, like oils & lipids.) Polar molecules: Assymmetry = polar soluble in polar solvents like water Nonpolar molecules: Symmetry = nonpolar soluble in nonpolar solvents like hexane Polar compound will dissolve in water Nonpolar compound

Properties of Organic Compounds Conductivity in Solution Organic Molecules DO NOT ionize in solution Therefore, they don’t conduct in solution and are NONELECTROLYTES Important Exception: ORGANIC ACIDS Ex: CH3COOH

Properties of Organic Compounds Undergo combustion or burn readily Complete and balance this combustion reaction C3H8 + O2 → ____ + ______

Properties of Organic Compounds Have slow rates of reaction Due to complexity of bonds Often catalyst is needed to speed up reactions React more slowly than ionics Tend to breakdown or decompose at low temperatures Compared to other compounds

Formula Writing & Drawing Molecules Types of Formulas Molecular Ex: Empirical Ex: Structural Ex: Condensed Structural Ex

Organic Prefixes (Table P) 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) Each member of the series differs by one carbon and a certain # of hydrogen

Alkanes General Formula: CnH2n+2 Single bonds between carbon atoms Name ends in “ane” SATURATED hydrocarbons (holding as many hydrogen atoms as possible)

Alkenes General Formula: CnH2n One double carbon to carbon bond *Address needed for bond location Name ends in “ene” UNSATURATED hydrocarbons (not totally filled with hydrogen)

Unsaturated = it isn’t “saturated” with hydrogen https://www.youtube.com/watch?v=Sfm3eHe57PU

Alkynes General Formula: CnH2n-2 One triple carbon to carbon bond *Address needed for bond location Name ends in “yne” UNSATURATED hydrocarbons (not totally filled with hydrogen)

What is molecular formula for these compounds? _____________ Note how it matches general formula CnH2n-2

dienes, diynes etc… Have multiple double or triple bonds. Give the address for each multiple bond. 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. Name of Diene: ___________________

Branching Hydrocarbons Have hydrocarbon “branches” off the main carbon chain. Called “alkyl” groups Name of Branched Hydrocarbon: ______________________

Naming Branched Hydrocarbons Find longest continuous carbon chain and name it (parent chain) Find address of each branch Count carbons in each branch Name branches using prefix ending in “yl” 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

Remember: First find the longest carbon chain and name it!! Name of compound: ___________________ Name : ___________________ Name: ______________________ Remember: First find the longest carbon chain and name it!!

What are the names of these compounds? Hint: find the longest continuous chain of carbon atoms and name it.

Isomers Same molecular formulas, but different structural formulas. https://www.youtube.com/watch?v=NgzFok_BA_0 Same molecular formulas, but different structural formulas. Atoms in molecule have a different arrangement. The more atoms the larger # possible isomers The more carbon atoms, the more possible arrangements of atoms! http://www.kentchemistry.com/links/organic/isomersofalkanes.htm

2 isomers with same molecular formula. Can you draw another isomer below with the same molecular formula?

Cyclical Hydrocarbons Form rings Start with “cyclo-” Shows skeleton of molecule only as a type of shorthand http://www.kentchemistry.com/links/organic/orgonaming7.htm

Benzene Series Benzene Series: CnH2n-6 alternating double bonds. 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 http://www.kentchemistry.com/links/organic/orgonaming4.htm

Ortho/Meta/Para locations

Organic Functional Groups Reference Table R

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

Name of this compound: ________________________

Alcohols 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 Draw a Picture of Glycerol:

Examples of Alcohols

Types of Alcohols Primary Secondary Tertiary http://www.kentchemistry.com/links/organic/alcohols.htm

Aldehydes Carbon double bonded to oxygen at end of a carbon chain (“carbonyl” group) ADDRESS NOT NEEDED (always at end!) End in “–al” Note: no address needed for functional group! http://www.kentchemistry.com/links/organic/Aldehydes.htm

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

Name this ketone: ____________________________ Note the basic difference between ketone and aldehydes Name this ketone: ____________________________

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

Name of Ether: ___________________

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

Name of Organic Acid: _______________________ Name of Organic Acid: _______________________ Name of Organic Acid: _______________________

Esters Within the chain, there is an oxygen atom that is next to a carbon double bonded to oxygen Name both sides around the oxygen atom Side with carbon “Alkyl” branch, ends in “yl” Side with the double bonded oxygen ends in “oate”

Name of Ester: _________________

Amines Have an “amine” group containing nitrogen. Use address Ends in “-amine” Important Example: Amino Acid Draw basic Amino Acid Name of Amine: ______________________

Or can have 2 or 3 branches named like alkyl groups Name of Amine: ______________________________

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

The nitrogen can also be central instead of at the end, with alkyl branches. Name of Amide: __________________________ Name of Amide: _____________________________

Organic Reactions Combustion Fermentation Substitution & Addition Polymerization Esterification Saponification Fractional Distillation Cracking

Combustion Burning or oxidation of a hydrocarbon. Needs O2 Produces CO2 and H2O Always EXOTHERMIC If not enough O2 present, you can get “incomplete” combustion resulting in carbon monoxide (CO) and soot (C).

Fermentation Makes ALCOHOL!!! Sugar is metabolized by yeast enzymes to make ethanol and CO2 How stuff works: (2:10) http://science.howstuffworks.com/innovation/34874-howstuffworks-show-episode-5-fermentation-video.htm

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

Addition ALKENES and ALKYNES. Add atoms without removing hydrogen Double or triple bond “opens up” Two atoms “add on” for each broken bond Results in ONE product.

Ex: Halogen Addition Hydrogenation

Polymerization Joining together of many individual “monomers” to make a “polymer”. Ex: Synthetic Polymers Nylon Rayon Polyethelene Polystyrene (styrofoam) Polyester Ex: Natural Polymers DNA/RNA Starch, Cellulose Proteins http://www.kentchemistry.com/links/organic/polymers.htm http://www.kentchemistry.com/links/organic/polymersswf.htm

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

Addition Polymerization

Joining Amino Acid Monomers H2O is also a product! CONDENSATION POLYMERIZATION

***Esterification*** Dehydration synthesis (water is removed to join molecules) Alcohol + Organic Acid Ester + Water Ester molecules often have nice odors Fats are a type of ester made of glycerol and 3 fatty acid chains Esterification Demo: https://www.edumedia-sciences.com/en/media/701

Name of Alcohol: ___________________ Name of Org. Acid __________________ Name of Ester: ____________________ Other product is always water!!

Saponification (Making Soap) Soap molecules are long molecules that are nonpolar at one end & polar at the other end. Can bring oil and water together Ester + Base Glycerol + Soap Saponification Process: (3:30) https://www.youtube.com/watch?v=NeqwrMxS_o0 Cleansing action of soap (2:00): https://www.youtube.com/watch?v=kG8dlCUd8oc

Petroleum Processing

Fractional Distillation Separation of a petroleum mixture by differences in Boiling Point temperature. Most compounds in petroleum are non-polar hydrocarbons. Larger chains = stronger VDW = higher BP Smaller chains = weaker VDW = lower BP Fractional Distillation: (4 min) https://www.youtube.com/watch?v=PYMWUz7TC3A

Cracking Breaking of long hydrocarbon chains into smaller ones. Often used on long chain hydrocarbons found in petroleum to make them into more usable fuels. Usually involves a catalyst Catalytic Cracking and Why it is done: (3:50) https://www.youtube.com/watch?v=Xsqlv4rWnEg

Examples of Cracking