Why Study Organic Chemistry? What substance is considered the most addictive? What is the most...
Transcript of Why Study Organic Chemistry? What substance is considered the most addictive? What is the most...
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, ...