introductory organic chemistry · chem 212 nicolas moitessier the birth of organic chemistry...
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CHEM 212 Nicolas Moitessier
Organic Chemistry 1
CHEM 212
CHEM 212 Nicolas Moitessier
Coming Up…
Information
Introduction: What is Organic Chemistry ?
Structures: Ch. 1.3
Alkanes: Ch. 2.1-2.3
Functional groups: Ch. 2.5-2.13
Chemical Bonding & Lewis Structures: Ch. 1.4-1.6
Formal Charges and Resonance: Ch. 1.7-1.8
VSEPR Theory Ch. 1.16
Hybridization Ch. 1.11-1.15
CHEM 212 Nicolas Moitessier
INFORMATION
CHEM 212 Nicolas Moitessier
You will get a great mark !!!
Otto Maass Building [email protected]
Office hours: anytime you need help
I will answer to all the e-mails (either by e-mail or in class)
Tutorials: Fridays 3:30 – 4:30
Sample questions provided with each lecture
CHEM 212 Nicolas Moitessier
Course Outline
Bonding Nomenclature, Functional groups AlkanesStereochemistryAlkyl HalidesAromatic Chemistry
CHEM 212 Nicolas Moitessier
Textbooks
CHEM 212 Nicolas Moitessier
Molecular Model Set
CHEM 212 Nicolas Moitessier
Available basement of Otto MaassChemistry Building
SyllabusCourse InformationProblemsPast Exams
CHEM 212 Nicolas Moitessier
Evaluation
mid-terms 30%
lab 25%
final exam 45%
CHEM 212 Nicolas Moitessier
Evaluation
2 mid-term exams
Feb. 9March. 9
6:00 - 9:00 pmOM112
CHEM 212 Nicolas Moitessier
Laboratory
Start next week
If you have not done so you must verify your lab day with Mike Daoust in Room 128 in the Otto MaassChemistry Building.
Available basement of Otto Maass Chemistry Building
Lab ManualLab coatSafety Glasses
CHEM 212 Nicolas Moitessier
Lecture Website
Lectures and course outline on:http://ww2.mcgill.ca/chemistry/undergrad/courses/212.shtml
Previous term lectureshttp://cool.mcgill.ca/
CHEM 212 Nicolas Moitessier
CHEM 212
Answers the following questions (theory):What is an organic molecule ?What is the name of this organic molecule?What is the reactivity of this organic molecule?What is the product of the reaction between these two molecules?
Why organic chemistry? (general knowledge)The organic chemistry in your daily lifeThe organic chemistry in the labThe past, present and future of this discipline
CHEM 212 Nicolas Moitessier
Information
Introduction: What is Organic Chemistry ?
Structures: Ch. 1.3
Alkanes: Ch. 2.1-2.3
Functional groups: Ch. 2.5-2.13
Chemical Bonding & Lewis Structures: Ch. 1.4-1.6
Formal Charges and Resonance: Ch. 1.7-1.8
VSEPR Theory Ch. 1.16
Hybridization Ch. 1.11-1.15
CHEM 212 Nicolas Moitessier
What is Organic Chemistry?
CHEM 212 Nicolas Moitessier
Organic vs. Inorganic
Before there was chemistry, there was AlchemyLate 1700s
Organic compounds can be extracted from living organisms The vital force…
1828: F. WöhlerSynthesis of organic compounds from inorganic sources
H2N NH2
O
NH4+ NCO- heat
CHEM 212 Nicolas Moitessier
The Birth of Organic Chemistry
Antoine Lavoisier, 1784Organic compounds composed of C, N, O
Cannizzaromolecular structure of organic compounds. he fixed the weight of the carbon atom at 12
August Kekule1861: Marsh gas: CHHHH"The carbon atoms form the skeleton for the molecule. Other atoms are attached to the skeleton much as hand and feet would be. It can seem strange that carbon atoms should cling together in lines or rows. Other atoms, in any usual compound, do not do this. Perhaps that is the reason why carbon's chemistry seems so different from that of other elements."
CHEM 212 Nicolas Moitessier
The Birth of Organic Chemistry
Kekule and the benzene moleculeKekule makes use of a dream "The carbon atoms of benzene form a ring."
Every organic compound possess a carbon skeleton (arranged as chains, rings or a mixture).
Organic chemistry: Understanding of these arrangementsManipulation of these skeletons (removing or adding parts)
CHEM 212 Nicolas Moitessier
Organic Chemistry
Isolation/Identification of compounds
Reaction of compoundsSynthesisMechanism
CHEM 212 Nicolas Moitessier
Organic Chemistry
Man on the street: explosive, danger…no other science is connected with more bad emotions, refusal and anxiety across wide sectors of society.
CHEM 212 Nicolas Moitessier
Bhopal, India Tragedy
Union Carbide, 1984.An explosion released 40 tons of ("registered") toxic substances (Methyl isocyanate) that killed more than 3,000 people and injured 200,000.
CHEM 212 Nicolas Moitessier
Exxon Valdez Spill
1989, Tanker Exxon Valdez grounded on a reefIt spilled about 40 M of crude oil Environmental harmOiled wildlife
CHEM 212 Nicolas Moitessier
Organic Chemistry
Man on the street: explosive, danger…Us AND for the man on the street; better quality of life
CHEM 212 Nicolas Moitessier
Sildenafil Citrate
O
CH3
N
HNN
N
O CH3
CH3
SN
NH3C
O O
VIAGRAPfizer: “Millions of men have found that VIAGRA is a great way to treat their erectile dysfunction (ED).”
CHEM 212 Nicolas Moitessier
For Ladies
Make-up, shampoo, Perfume, …
CHEM 212 Nicolas Moitessier
Cosmetics
MOISTURIZERS function as a moisture barrier or to attract moisture from the environment:
cetyl alcohol (keeps oil and water from separating), dimethicone silicone (skin condition and anti-foam ingredient), lanolin and lanolin alcohols and oil (skin andhair conditioners), octyl dodecanol (skin conditioner), oleic acid (olive oil), panthenol (vitamin B-complex derivative, hair conditioner), stearic acid and stearylalcohol
PRESERVATIVES and antioxidants (including vitamins) prevent product deterioration:
trisodium and tetrasodium edetate (EDTA), tocopherol (vitamin E) ANTIMICROBIALS fight bacteria:
butyl, propyl, ethyl, and methyl parabens, DMDM hydantoin, methylisothiazolinone, phenoxyethanol, quaternium-15
THICKENERS and waxes used in stick products such as lipsticks and blushers:
candelilla, carnauba, and microcrystalline waxes, carbomer and polyethylene thickeners
SOLVENTS used to dilute: butylene glycol and propylene glycol, cyclomethicone (volatile silicone), ethanol (alcohol), glycerin
CHEM 212 Nicolas Moitessier
Cosmetics
EMULSIFIERS break up and refine: glyceryl monostearate (also pearlescent agent), lauramide DEA (also foam booster), polysorbates
COLOR additives:Synthetic ORGANIC colors derived from coal and petroleum sources, INORGANIC pigments, iron oxides, mica (iridescent)
HAIR DYES - phenol derivatives used in combination with other chemicals in permanent (two-step) hair dyes: pH ADJUSTERS stabilize or adjust acids and bases (ammonium hydroxide, citric acid, triethanolamine) pH adjuster used mostly in transparent soap OTHERS:sodium lauryl sulfate - detergent stearic acid - cleansing, emulsifier
CHEM 212 Nicolas Moitessier
And also
Food (preservatives, …)Materials
PlasticKevlar ® (bulletproof vest, …Nylon ® (cloth, fishing,….PlexiGlass® (discovered at McGill)And other polymers (tires, …)PaperInk …
CHEM 212 Nicolas Moitessier
AND YOU!
YOU: DNA, Proteins (enzymes, cell membrane receptors, Carbohydrates (Polysaccharides,…Lipids (fatty acids,…
And what you eatProteinCarbohydrateLipids
The plants: from CO2 to complex organic molecules
… with no complex, noisy, polluting, smelly factory!
CHEM 212 Nicolas Moitessier
What are you made of?
Oxygen 65%Carbon 18% Hydrogen 10% Nitrogen 3% Calcium 1.5% Phosphorus 1.0% Potassium 0.35% Sulfur 0.25% Sodium 0.15% Magnesium 0.05% Copper, Zinc, Selenium, Molybdenum, Fluorine, Chlorine, Iodine, Manganese, Cobalt, Iron (0.70%) Lithium, Strontium, Aluminum, Silicon, Lead, Vanadium, Arsenic, Bromine (trace amounts) YOU ARE MOSTLY INORGANIC !!!
CHEM 212 Nicolas Moitessier
What is a “chemical”?
What is a chemical for the man on the street?Is NaCl a chemical?
A product of a chemical process? > NaCl is a chemicalA unnatural product? > NaCl is not a chemicalA toxic product? > NaCl (pure) is not a chemical
Wrong definitions from the mediaChemical = dangerBio = safeA synthetic compound (highly pure) is safer than the same non-pure compound extracted from plants !!!
CHEM 212 Nicolas Moitessier
What for?
Answering questions and solving problemsDoes eating turkey make you sleepy?
Turkey contains L-tryptophan, (amino acid with known sleep inducing effect)L-tryptophan is used in the body to produce B-vitamin,B-vitamin is used to produce serotonin, a neurotransmitter with known calming effects L-tryptophan needs to be taken without any other amino acids or protein in order to make you drowsy. It's not the only food on the table. Fats also take a lot of energy to digest,Alcohol is a central nervous system depressant. ….
CHEM 212 Nicolas Moitessier
What for?
Why did he leave?Initially:
First, there's attraction. Part of the nonverbal communication may involve pheromones, a form of chemical communication.raw lust is characterized by high levels of testosteroneThe pounding heart is caused by higher levels of norepinepherineThe love is due to a rush of phenylethylamine and dopamine.
Then…Lasting love confers chemical benefits in the form of stabilized production of serotonin and oxytocin. Suppression of vasopressin can cause males to abandon their love nest and seek new mates.
CHEM 212 Nicolas Moitessier
5 Messages
You are chemistry!... and the rest of the universe, too!Chemistry invents new matter à la carte! In chemistry there are no copies of molecules, only identical originals!
synthetic vs. naturalerroneous belief whereby "chemical" is the opposite of "natural"and hence must be bad.Molecules are the same - whatever their different origin!
Chemistry provides solutions to its own problems! It can therefore be used to remove polluting substances and clean up the environment
There are no toxic substances, only toxic doses! even water is toxic: water intoxication and the related problem resulting from the dilution of sodium in the body, hyponatremia.
http://chemistry.about.com/ http://www.chemforlife.org/
CHEM 212 Nicolas Moitessier
Information
Introduction: What is Organic Chemistry ?
Structures: Ch. 1.3
Alkanes: Ch. 2.1-2.3
Functional groups: Ch. 2.5-2.13
Chemical Bonding & Lewis Structures: Ch. 1.4-1.6
Formal Charges and Resonance: Ch. 1.7-1.8
VSEPR Theory Ch. 1.16
Hybridization Ch. 1.11-1.15
CHEM 212 Nicolas Moitessier
Structures
Structural TheoryCentral Premises
Valency: atoms in organic compounds form a fixed number of bonds
Carbon can form one or more bonds to other carbons
C O H F
Carbon: tetravalent
Oxygen: Divalent
Hydrogen: monovalent
Halogen: monovalent
C C
CHEM 212 Nicolas Moitessier
Structural Formulas
Molecular FormulaC3H8O2
Condensed FormulaCH3CH2OCH3
Dash Formula
Bond line Formula
H C C O
H H
C
H
H
H
HH
O
CHEM 212 Nicolas Moitessier
Structural Formulas
Identical molecules or constitutional isomers?
Molecular Formula: C6H14
IdenticalCH3(CH2)2CH(CH3)2
CHEM 212 Nicolas Moitessier
Structural Formulas
Identical molecules or constitutional isomers?Molecular Formula: C6H14
Constitutional isomers
• Difference of connectivity (sequence of bonds)
CHEM 212 Nicolas Moitessier
Isomers
Vitamin A, C20H30O
Ferruginol, C20H30OOH
OH
CHEM 212 Nicolas Moitessier
Information
Introduction: What is Organic Chemistry ?
Structures: Ch. 1.3
Alkanes: Ch. 2.1-2.3
Functional groups: Ch. 2.5-2.13
Chemical Bonding & Lewis Structures: Ch. 1.4-1.6
Formal Charges and Resonance: Ch. 1.7-1.8
VSEPR Theory Ch. 1.16
Hybridization Ch. 1.11-1.15
CHEM 212 Nicolas Moitessier
Alkanes / Hydrocarbons
General formula CxHy
Aliphatic Aromaticlinear and cyclic hydrocarbons benzene and derivativesAlkanes cycloalkanes
Alkenes cycloalkenes
Alkynes
CHEM 212 Nicolas Moitessier
Alkanes
Methane CH4 Ethane C2H6
Propane C3H8 Butane C4H10
C
H
H
H
H C
H
H
H
C
H
H
H
C
H
H
H
C
H
H
C
H
H
H C
H
H
H
C
H
H
C
H
H
C
H
H
H
CHEM 212 Nicolas Moitessier
Alkanes
General Formula
CnH2n+2
n = 1: Methane n = 2: Ethanen = 3: Propane n = 4: Butanen = 5: Pentane n = 6: Hexanen = 7: Heptane` n = 8: Octane
CHEM 212 Nicolas Moitessier
Isomers
Pentane: 3 isomers
C
H
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
H C
H
H
C C
H
H
H
H C
H
H
H C
H
H
C
H
H
H
C
H
H
C
H
C
H
H
H
H C
H
H
CHEM 212 Nicolas Moitessier
Isomers
Hexanes, 5 isomers
… Eicosane (C20H42), 366,319 isomers