1. 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?

2. 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

3. 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?

4. How Important is Organic Chemistry in Daily Life?
Botulinum toxin is a protein and neurotoxin produced by the bacterium Clostridium botulinum
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
Asphalt, steel, and automotive lead batteries, depending on how it’s measured
Petroleum
OCTANITOCUBANE
Cellulose
Carbyne

5. 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

6. 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

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

9. 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)….

10. 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

11. 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.

12. Structural Isomers

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

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

15. Alkenes— Many Occur Naturally

16. 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

17. 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.

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

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

21. 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) = kJ/mol
∆Hrxn for C2H2 + O = –1300 kJ/mol

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

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

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

25. Functional Groups

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

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

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

29. GLYCOLS Alcohols with Two OH Groups
Propylene glycol
Ethylene glycol

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

31. Amines generally have terrible odors!
Pyridine
Cadaverine

32. Amines, like NH3, are bases

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

34. Compounds with Carbonyl Group
Aldehyde
Carboxylic acid
Ketone

35. Structures of Aldehydes
Cinnamaldehyde
Odors from aldehydes and ketones

36. 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

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

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

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

40. 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

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

42. Fats and Oils: Saponification

43. Acids + Amines --> AMIDES
N-methylacetamide

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