Why Study Organic Chemistry?What substance is considered the

most addictive?

What is the most consumed psychoactive substance in the world?

What percentage of North Americans use caffeine everyday?

What drug has the worst withdrawal symptoms?

What is the most abused drug?

What is the most used drug worldwide?

What class of drug is the most commonly prescribed?

What percentage of Americans takes at least one prescription drug daily?

What is the original source for the drugs Vicodin, Percocet, Oxycodone, Oxycontin, and Percodan?

What class of drug is responsible for the most reported poisonings of any substance?

Why Study Organic Chemistry?

Nicotine

90%

Marijuana

Caffiene

Opioid analgesics such as morphine, hydrocodone, oxycodone, methadone

Lipid regulators, followed by antidepressants and then narcotic analgesics

Alcohol, followed by benzodiazapines and then opiatesOpium poppy

Nearly 70%Caffiene

How Important is Organic Chemistry in Daily Life?

What class of drug is responsible for the most poisoning deaths of any substance?

What is the most toxic substance known?

What is the starting material used to produce most pharmaceuticals?

Where does asphalt come from (and basketballs, lipstick, contact lenses, nylon)?

What is the most recycled material in the United States? What is the strongest

substance known?

What is the most explosive non-nuclear substance?

What is the world’s most abundant organic compound?

How Important is Organic Chemistry in Daily Life?

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-worldhttp://someinterestingfacts.net/top-10-most-deadliest-substance-known-to-man/

Botulinum toxin is a protein and neurotoxin produced by the bacterium Clostridium botulinum

Petroleumhttp://whgbetc.com/petro-products.pdf

Cellulose

OCTANITOCUBANEhttp://news.softpedia.com/news/The-Most-Powerful-Non-nuclear-Explosives-in-the-World-58104.shtml

Carbynehttp://cleantechnica.com/2013/10/10/carbyne-strongest-material-yet-known-possesses-number-useful-properties-research-finds/

Asphalt, steel, and automotive lead batteries, depending on how it’s measured

Petroleumhttp://www.petroleum.co.uk/other-uses-of-petroleum

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

• 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 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: Alkanes

Hydrocarbons & Structural Isomerism

C4H10 has 2 strucural isomers

C5H12 has 3

C6H14 has 5

C7H14 has 9

C8H18 has 18

Isomers of C5H12?

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

Cis-2-butene

Stereoisomers: Geometric

Geometric isomers can occur when there is a C=C double bond.

Trans-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

• The fat in bacon is partially unsaturated. The fat adds Br2 to the C=C bonds.

• Fats can be “hydrogenated” with H2.

Fat placed in Br2 vapor

An Addition Reaction

• Fats can be “hydrogenated” with H2.

Peanut butter has partially hydrogenated vegetable oil.

Trans Fatty Acidstend to raise total blood cholesterol

CH3(CH2)7CH=CH(CH2)7CO2H

Alkynes

• Alkynes have carbon-carbon triple bonds. • C2H2: common name = acetylene

systematic name = ethyne

Preparation:

CaC2(s) + H2O(liq) -->

C2H2 (g) + Ca(OH)2(s)∆Hf

o(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.

GLYCOLSAlcohols with Two OH Groups

Ethylene glycol

Propylene glycol

AminesAlcohols are derivatives of H2O (R–OH) and

amines are derivatives of NH3.

Methylamine Dimethylamine Trimethylamine

AminesAmines generally have terrible odors!

CadaverinePyridine

AminesAmines, like NH3, are bases

Amines

Many natural products and drugs (such as nicotine and cocaine) are bases.

NicotineH+

Compounds with Carbonyl Group

Aldehyde Carboxylic acid Ketone

Structures of Aldehydes

Cinnamaldehyde Odors from aldehydes and ketones

Carboxylic AcidsBenzoic acid

Carboxylic acid group with acidic H+

All are WEAK acids

Acetic acid

Acids are found in many natural substances: bread, fruits, milk, wine

Carboxylic Acids

Aspirin, acetylsalicylic acid

Formic acid, HCO2H, gives the

sting to ants.

Acids + Alcohols --> ESTERS

Esters have generally pleasant odors

Acids + Alcohols --> ESTERS

Many fruits such as bananas and strawberries contain esters.

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

AcetoaminophenTylenol, Datril, Momentum, ...