introductory organic chemistry - oocitieschem 212 nicolas moitessier you will get a great mark !!!...

CHEM 212 Nicolas Moitessier

Organic Chemistry 1

CHEM 212


Nicolas Moitessier

Otto Maass Building216

[email protected]


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


INFORMATION


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


Course Outline

Bonding Nomenclature, Functional groups AlkanesStereochemistryAlkyl HalidesAromatic Chemistry


Textbooks


Molecular Model Set


Available basement of Otto MaassChemistry Building

SyllabusCourse InformationProblemsPast Exams


Evaluation

mid-terms 30%

lab 25%

final exam 45%


Evaluation

2 mid-term exams

Feb. 9March. 9

6:00 - 9:00 pmOM112


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


Lecture Website

Lectures and course outline on:http://ww2.mcgill.ca/chemistry/undergrad/courses/212.shtml

Previous term lectureshttp://cool.mcgill.ca/


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


Information


Structures: Ch. 1.3








What is Organic Chemistry?


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


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."


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)


Organic Chemistry

Isolation/Identification of compounds

Reaction of compoundsSynthesisMechanism


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.


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.


Exxon Valdez Spill

1989, Tanker Exxon Valdez grounded on a reefIt spilled about 40 M of crude oil Environmental harmOiled wildlife


Organic Chemistry

Man on the street: explosive, danger…Us AND for the man on the street; better quality of life


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).”


For Ladies

Make-up, shampoo, Perfume, …


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


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


And also

Food (preservatives, …)Materials

PlasticKevlar ® (bulletproof vest, …Nylon ® (cloth, fishing,….PlexiGlass® (discovered at McGill)And other polymers (tires, …)PaperInk …


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!


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 !!!


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 !!!


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. ….


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.


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/


Information


Structures: Ch. 1.3








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


Structural Formulas

Molecular FormulaC3H8O2

Condensed FormulaCH3CH2OCH3

Dash Formula

Bond line Formula

H C C O

H H

C

H

H

H

HH

O


Structural Formulas

Identical molecules or constitutional isomers?

Molecular Formula: C6H14

IdenticalCH3(CH2)2CH(CH3)2


Structural Formulas

Identical molecules or constitutional isomers?Molecular Formula: C6H14

Constitutional isomers

• Difference of connectivity (sequence of bonds)


Isomers

Vitamin A, C20H30O

Ferruginol, C20H30OOH

OH


Information


Structures: Ch. 1.3








Alkanes / Hydrocarbons

General formula CxHy

Aliphatic Aromaticlinear and cyclic hydrocarbons benzene and derivativesAlkanes cycloalkanes

Alkenes cycloalkenes

Alkynes


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


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


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


Isomers

Hexanes, 5 isomers

… Eicosane (C20H42), 366,319 isomers

introductory organic chemistry - oocitieschem 212 nicolas moitessier you will get a great mark !!!...

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