Why Study Organic Chemistry? What substance is considered the most addictive? What drug has the worst withdrawal symptoms? What is the most abused drug? What percentage of North Americans use caffeine everyday? What is the most used drug worldwide? What is the original source for the drugs Vicodin, Percocet, Oxycodone, Oxycontin, and Percodan? What is the most consumed psychoactive substance in the world? What class of drug is responsible for the most reported poisonings of any substance? What percentage of Americans takes at least one prescription drug daily? What class of drug is the most commonly prescribed?

Why Study Organic Chemistry? Alcohol, followed by benzodiazapines and then opiates Nicotine Caffiene 90% Opium poppy Marijuana Opioid analgesics such as morphine, hydrocodone, oxycodone, methadone Nearly 70% Caffiene Lipid regulators, followed by antidepressants and then narcotic analgesics

How Important is Organic Chemistry in Daily Life? What is the most toxic substance known? What is the starting material used to produce most pharmaceuticals? What class of drug is responsible for the most poisoning deaths of any substance? What is the most recycled material in the United States? Where does asphalt come from (and basketballs, lipstick, contact lenses, nylon)? What is the most explosive non-nuclear substance? What is the world’s most abundant organic compound? What is the strongest substance known?

How Important is Organic Chemistry in Daily Life? Botulinum toxin is a protein and neurotoxin produced by the bacterium Clostridium botulinum Petroleum http://www.petroleum.co.uk/other-uses-of-petroleum Of accidental deaths in the US, poisoning is the #1 cause; 89% of poisoning deaths were due to drugs, and 77% of these deaths were unintentional; opioid analgesics account for 40% of these deaths http://io9.com/5861680/10-of-the-most-dangerous-chemicals-in-the-world http://someinterestingfacts.net/top-10-most-deadliest-substance-known-to-man/ Asphalt, steel, and automotive lead batteries, depending on how it’s measured Petroleum http://whgbetc.com/petro-products.pdf OCTANITOCUBANE http://news.softpedia.com/news/The-Most-Powerful-Non-nuclear-Explosives-in-the-World-58104.shtml Cellulose Carbyne http://cleantechnica.com/2013/10/10/carbyne-strongest-material-yet-known-possesses-number-useful-properties-research-finds/

Types of Organic Compounds Vast majority of over 20 million known compounds are based on C: organic compounds. Generally contain C and H + other elements Great variety of compounds

Hydrocarbons Compounds of C and H Subgroups: Alkanes: C-C single bonds Alkenes: C=C double bonds Alkynes: carbon-carbon triple bonds Aromatic: based on benzene

Hydrocarbons Alkanes have the general formula CnH2n+2 CH4 = methane C2H6 = ethane C3H8 = propane C4H10 = butane C5H12 = pentane

Hydrocarbons: Alkanes Alkanes are colorless gases, liquids, and solids Generally unreactive (but undergo combustion) Not polar (or low polarity) and so are not soluble in water. HOW TO NAME THEM (refer to equations book)….

Hydrocarbons & Structural Isomerism Isomers of C5H12? C4H10 has 2 strucural isomers C5H12 has 3 C6H14 has 5 C7H14 has 9 C8H18 has 18 Note names of isomers

Isomerism Isomers have identical composition but different structures Two forms of isomerism Constitutional or structural Stereoisomerism or geometric Structural Same empirical formula but different atom-to-atom connections Geometric Same atom-to-atom connections but different arrangement in space.

Structural Isomers

Stereoisomers: Geometric Geometric isomers can occur when there is a C=C double bond. Trans-2-butene Cis-2-butene

Alkenes: Compounds with C=C Double Bonds How many isomers are possible for a compound with the formula C4H8?

Alkenes— Many Occur Naturally

Reactions of Alkenes: ADDITION REACTIONS Alkenes are unsaturated — more bonds can form to the C atoms Molecules such as Br2, H2, HCl, HBr, and H2O add to the double bond

An Addition Reaction Fat placed in Br2 vapor The fat in bacon is partially unsaturated. The fat adds Br2 to the C=C bonds. Fats can be “hydrogenated” with H2.

An Addition Reaction Fats can be “hydrogenated” with H2. Peanut butter has partially hydrogenated vegetable oil.

Trans Fatty Acids tend to raise total blood cholesterol CH3(CH2)7CH=CH(CH2)7CO2H Trans Fatty Acids tend to raise total blood cholesterol

Alkynes Preparation: CaC2(s) + H2O(liq) --> C2H2 (g) + Ca(OH)2(s) Alkynes have carbon-carbon triple bonds. C2H2: common name = acetylene systematic name = ethyne Preparation: CaC2(s) + H2O(liq) --> C2H2 (g) + Ca(OH)2(s) ∆Hfo(C2H2, g) = +226.7 kJ/mol ∆Hrxn for C2H2 + O2 = –1300 kJ/mol

Aromatic Compounds Benzene, C6H6, in the top 25 chemicals produced in the U.S. Starting point for hundreds of other compounds.

Resonance in Benzene C6H6 has two resonance structures with alternating double bonds. The π electrons are delocalized over the ring.

Resonance in Benzene C–C single bond = 154 pm C=C bond = 134 pm CC bonds in benzene = 139 pm π electrons delocalized

Functional Groups

Alcohols Characterized by –OH group Name: add –ol to name of hydrocarbon Methanol Butanol

Structures of Alcohols C3H5OH: how many structural isomers? Naming: Add -ol to name of 3-C hydrocarbon. Indicate position of OH with number.

Alcohol Properties Alcohols are a derivative of water Many alcohols dissolve in water Methanol dissolves in water. Butanol is NOT soluble in water.

GLYCOLS Alcohols with Two OH Groups Propylene glycol Ethylene glycol

Amines Alcohols are derivatives of H2O (R–OH) and amines are derivatives of NH3. Trimethylamine Dimethylamine Methylamine

Amines generally have terrible odors! Pyridine Cadaverine

Amines, like NH3, are bases

Amines Many natural products and drugs (such as nicotine and cocaine) are bases. H+ Nicotine

Compounds with Carbonyl Group Aldehyde Carboxylic acid Ketone

Structures of Aldehydes Cinnamaldehyde Odors from aldehydes and ketones

Carboxylic acid group with acidic H+ Carboxylic Acids Benzoic acid Acetic acid Carboxylic acid group with acidic H+ All are WEAK acids Acids are found in many natural substances: bread, fruits, milk, wine

Formic acid, HCO2H, gives the sting to ants. Carboxylic Acids Aspirin, acetylsalicylic acid

Acids + Alcohols --> ESTERS Esters have generally pleasant odors

Acids + Alcohols --> ESTERS Many fruits such as bananas and strawberries contain esters.

Fats with C=C bonds are usually LIQUiDS Fats and Oils Fats with C=C bonds are usually LIQUiDS Oleic acid: a monounsaturated fatty acid C=C bond

Fats and Oils Fats with saturated acids (no C=C bonds) are SOLIDS. Saturated fats are more common in animals.

Fats and Oils: Saponification

Acids + Amines --> AMIDES N-methylacetamide

Acids + Amines --> AMIDES Acetoaminophen Tylenol, Datril, Momentum, ...