CHEM 212 - OoCities
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Organic Chemistry 1 CHEM 212 CHEM 212 Nicolas Moitessier Nicolas Moitessier Otto Maass Building 216 nicolas.moitessier@mcgill.ca 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 216 nicolas.moitessier@mcgill.ca 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 Alkanes Stereochemistry Alkyl Halides Aromatic Chemistry CHEM 212 Nicolas Moitessier Textbooks CHEM 212 Nicolas Moitessier Molecular Model Set CHEM 212 Nicolas Moitessier Available basement of Otto Maass Chemistry Building Syllabus Course Information Problems Past Exams CHEM 212 Nicolas Moitessier Evaluation CHEM 212 mid-terms 30% lab 25% final exam 45% Nicolas Moitessier Evaluation 2 mid-term exams Feb. 9 March. 9 6:00 - 9:00 pm OM112 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 Maass Chemistry Building. Available basement of Otto Maass Chemistry Building z Lab Manual z Lab coat z Safety Glasses CHEM 212 Nicolas Moitessier Lecture Website Lectures and course outline on: http://ww2.mcgill.ca/chemistry/undergrad/courses/212.shtml Previous term lectures http://cool.mcgill.ca/ CHEM 212 Nicolas Moitessier CHEM 212 Answers the following questions (theory): z What is an organic molecule ? z What is the name of this organic molecule? z What is the reactivity of this organic molecule? z What is the product of the reaction between these two molecules? Why organic chemistry? (general knowledge) z The organic chemistry in your daily life z The organic chemistry in the lab z The 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 Alchemy Late 1700s z Organic compounds can be extracted from living organisms z The vital force… 1828: F. Wöhler z Synthesis of organic compounds from inorganic sources O NH4+ CHEM 212 - NCO heat H2N NH2 Nicolas Moitessier The Birth of Organic Chemistry Antoine Lavoisier, 1784 z Cannizzaro z z molecular structure of organic compounds. he fixed the weight of the carbon atom at 12 August Kekule z z CHEM 212 Organic compounds composed of C, N, O 1861: 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." Nicolas Moitessier The Birth of Organic Chemistry Kekule and the benzene molecule z Kekule makes use of a dream z "The carbon atoms of benzene form a ring." Every organic compound possess a carbon skeleton (arranged as chains, rings or a mixture). Organic chemistry: z Understanding of these arrangements z Manipulation of these skeletons (removing or adding parts) CHEM 212 Nicolas Moitessier Organic Chemistry Isolation/Identification of compounds Reaction of compounds z Synthesis z Mechanism 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 reef It spilled about 40 M of crude oil Environmental harm Oiled 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 O N H 3C N O N HN S CH3 N N CH3 O CH3 VIAGRA Pfizer: “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: z cetyl alcohol (keeps oil and water from separating), dimethicone silicone (skin condition and anti-foam ingredient), lanolin and lanolin alcohols and oil (skin and hair conditioners), octyl dodecanol (skin conditioner), oleic acid (olive oil), panthenol (vitamin B-complex derivative, hair conditioner), stearic acid and stearyl alcohol PRESERVATIVES and antioxidants (including vitamins) prevent product deterioration: z trisodium and tetrasodium edetate (EDTA), tocopherol (vitamin E) ANTIMICROBIALS fight bacteria: z butyl, propyl, ethyl, and methyl parabens, DMDM hydantoin, methylisothiazolinone, phenoxyethanol, quaternium-15 THICKENERS and waxes used in stick products such as lipsticks and blushers: z candelilla, carnauba, and microcrystalline waxes, carbomer and polyethylene thickeners SOLVENTS used to dilute: z butylene glycol and propylene glycol, cyclomethicone (volatile silicone), ethanol (alcohol), glycerin CHEM 212 Nicolas Moitessier Cosmetics EMULSIFIERS break up and refine: z glyceryl monostearate (also pearlescent agent), lauramide DEA (also foam booster), polysorbates COLOR additives: z 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: CHEM 212 sodium lauryl sulfate - detergent stearic acid - cleansing, emulsifier Nicolas Moitessier And also Food (preservatives, …) Materials z Plastic z Kevlar ® (bulletproof vest, … z Nylon ® (cloth, fishing,…. z PlexiGlass® (discovered at McGill) z And other polymers (tires, …) z Paper z Ink z … CHEM 212 Nicolas Moitessier AND YOU! z YOU: ÎDNA, ÎProteins (enzymes, cell membrane receptors, ÎCarbohydrates (Polysaccharides,… ÎLipids (fatty acids,… z And what you eat ÎProtein ÎCarbohydrate ÎLipids z The plants: from CO2 to complex organic molecules Î… 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? z A product of a chemical process? > NaCl is a chemical z A unnatural product? > NaCl is not a chemical z A toxic product? > NaCl (pure) is not a chemical Wrong definitions from the media z Chemical = danger z Bio = safe z A 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 problems Does eating turkey make you sleepy? z Turkey contains L-tryptophan, (amino acid with known sleep z z z z z z z CHEM 212 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. …. Nicolas Moitessier What for? Why did he leave? z Initially: Î First, there's attraction. Î Part of the nonverbal communication may involve pheromones, a form of chemical communication. Î raw lust is characterized by high levels of testosterone Î The pounding heart is caused by higher levels of norepinepherine Î The love is due to a rush of phenylethylamine and dopamine. z Then… Î Lasting love confers chemical benefits in the form of stabilized production of serotonin and oxytocin. Î 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! z synthetic vs. natural z erroneous belief whereby "chemical" is the opposite of "natural" and hence must be bad. z Molecules are the same - whatever their different origin! Chemistry provides solutions to its own problems! z It can therefore be used to remove polluting substances and clean up the environment There are no toxic substances, only toxic doses! z even water is toxic: water intoxication and the related problem resulting from the dilution of sodium in the body, hyponatremia. http://chemistry.about.com/ CHEM 212 http://www.chemforlife.org/ 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 Theory z Central Premises ÎValency: atoms in organic compounds form a fixed number of bonds C Carbon: tetravalent O H Oxygen: Divalent Hydrogen: monovalent F Halogen: monovalent ÎCarbon can form one or more bonds to other carbons C CHEM 212 C Nicolas Moitessier Structural Formulas Molecular Formula z C3H8O2 Condensed Formula z CH3CH2OCH3 Dash Formula H H H C C H H H O C H H Bond line Formula O CHEM 212 Nicolas Moitessier Structural Formulas Identical molecules or constitutional isomers? z Molecular Formula: C6H14 Identical z CH3(CH2)2CH(CH3)2 CHEM 212 Nicolas Moitessier Structural Formulas Identical molecules or constitutional isomers? z Molecular Formula: C6H14 Constitutional isomers • CHEM 212 Difference of connectivity (sequence of bonds) Nicolas Moitessier Isomers Vitamin A, C20H30O OH Ferruginol, C20H30O CHEM 212 OH 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 linear and cyclic hydrocarbons Alkanes cycloalkanes Alkenes cycloalkenes Aromatic benzene and derivatives Alkynes CHEM 212 Nicolas Moitessier Alkanes Methane CH4 Ethane C2H6 H H C H H H Propane C3H8 H CHEM 212 H H H C C C H H H H H C C H H H Butane C4H10 H H H H H H C C C C H H H H H Nicolas Moitessier Alkanes General Formula CnH2n+2 n = 1: Methane n = 3: Propane n = 5: Pentane n = 7: Heptane` CHEM 212 n = 2: Ethane n = 4: Butane n = 6: Hexane n = 8: Octane Nicolas Moitessier Isomers Pentane: 3 isomers H H H H H C C H C H H H H C C C C C H H H H H H H H C H H H H C H H H H H H H C C C C H H H C H H H H CHEM 212 Nicolas Moitessier Isomers Hexanes, 5 isomers … Eicosane (C20H42), 366,319 isomers CHEM 212 Nicolas Moitessier
