Transcript: OCT 2015 Fact Eight By Collin O'Toole fact three The incident led to a more in-tune regional response to hazardous material spills and cooperation among agencies. period 1 On June 20,1992 at 2:50 A.M., 14 train cars fell 71 feet into the Nemadj River. A few of the train cars contained hazardous materials. According to the report from the National Transportation Safety Board (NTSB), the curve at 12A had a very small crack, but met Federal Railroads Administration (FRA) requirements so it was not repaired. Fact Six fact four Fact Seven Thousands of fish died, rose to the surface and were grabbed my all kinds of birds. Fact Ten They looked all over the rails for days and weeks to find other evidence and nothing was ever found that caused the accident. fact Two Fact Five Fact Nine Fact one From what I have read is that the rails were damaged. It was damaged inside the steel and out of sight so you would half to use a magnifying glass to find it. Benzene Spill in Superior 21,800 gallons of benzene spilled out through a foot wide gash in the tanker car. 30,000 people were evacuated from Duluth, Superior, and some from Washburn. Law enforcement was investigating the big cloud and there were many of reports of illness. Benzene: is a colorless, flammable liquid with sweet odor. It evaporates quickly when exposed to air. Benzene is also a natural part of crude oil and gasoline. Thank you! Benzene spilled into a river and created a big cloud 20 miles long and 5 miles wide.
Transcript: BACKING KEKULÉ'S THEORY BENZENE STRUCTURE BEFORE KEKULÉ KEKULÉ Benzene ring theory Kekulé said that he was day-dreaming and a vision of a snake biting his own tail came up and therefore this inspired him to create the theory of the benzene ring. He claims that this vision came to him after years of studying the nature of carbon-carbon bonds. HOW KEKULÉ CAME UP WITH THE BENZENE RING THEORY Michael Faraday first identified Benzene in 1825 from the oily residue from the production of illuminating gas. Eilhard Mitscherlich first produced it in 1833 by distilling benzoic acid. HISTORY THE PROBLEM In 1865 Kekulé came up with a theory about benzene's structure where the carbon atoms were arranged in a ring with alternating single and double bonds. Benzene has a C6H6 formula, so there was a doubt about benzene's structure. Kekulé suggested that the carbon atoms were arranged in a ring with alternate single and double bonds. For every monoderivative of benzene C6H5X, where X = Cl, OH, CH3, NH2, etc.)only one isomer was ever found, implying that all six carbons are equivalent, so that substitution on any carbon gives only a single possible product. For diderivatives such as the toluidines, C6H4(NH2)(CH3), three isomers were observed, for which Kekulé proposed structures with the two substituted carbon atoms separated by one, two and three carbon-carbon bonds. Archibald Scott Couper in 1858 and Joseph Loschmidt in 1861suggested possible structures that contained multiple double bonds or multiple rings, but too little evidence was then available for chemists decide on any particular structure. Claus (1867), Dewar (1867), Ladenburg (1869), Armstrong (1887), Thiele (1899) and Kekulé (1865).
Transcript: Benzene What is it? Organic Compound Colorless/Light yellow liquid Aromatic Compound Highly Flamable Volatile Heavier than air Slightly soluble in water C6H6 Human Carcinogen - Derived from the word "gum benzoin" - Benzoin is derived from a tree - Sublimation of benzoin to produce benzoic acid - The hydrocarbon derived from benzoic acid is called benzene Research and Production Past Aftershave Decaffeinate Coffee Used in gasoline Current Most commonly used as an intermediate - Unfixed Bonds -> Resonating Structure Making Connections with SCH4U (cc) photo by Metro Centric on Flickr Uses Oily residue of an illuminating gas Chemical Composition Cancer 1825 Budapest Chemical Structure Named the compound benzin San Francisco Distillation of benzoic acid and lime. Developmental Effects First to isolate and indentify Benzene Gurteg is awesome! Health Effects Stockholm Eilhard Mitscherlic Reproductive Effects (cc) photo by jimmyharris on Flickr 1833 Michael Faraday Human Carcinogen (cc) photo by Franco Folini on Flickr Leukemia C6H6 Death 6 Carbons 6 Hydrogens (cc) photo by Metro Centric on Flickr (Characteristics) Naming Benzene
Transcript: Characteristics What is Benzene? When you buy CDs, throw-away cutlery or anything wrapped in plastic (f.ex: peanuts or crisps) you are buying benzene. Colorless, highly flammable liquid Is an aromatic hydrocarbon (a hydrocarbon with alternating double and single bonds between carbon atoms forming rings Is also an organic compound (meaning it consists of carbon and at least one other element.) It is a hydrocarbon (only consisting of hydrogen and carbon atoms). Benzene Is mainly used to add to other elements, such as: ~in gasoline ~in plastics ~nylon tights
Transcript: ASTDR & HSEES • Air VS Food Levels Government • 5ppb Maximum in Water vomiting • Develop Recommendations for Toxic Substances Medical Test • In the Ground confusion • "Not-to-Exceed" Levels dizziness sleepiness Human Exposure • Numerous Tests • In the Air Description Uses Cancer • Regulations & Recommendations • Able to Call for More Info Environment rapid heart rate • Everyone is Exposed • Industrial Uses • Natural Sources unconsciousness • Leukemia Case Study • Many Issues: • Liquid w/Sweet Odor (frozen Benzene) • Industrial Areas tremors drowsiness headaches • Exposure in Australia ... and death. • Enter Lungs --> Bloodsteam • Industrial Sources • One per 10,000 at Excess Lifetime Risk Benzene (bottle of benzene) irritation • Blood Analysis Human Health coma
Transcript: Benzene Benzene is found in... - workplace - crude oil - printers - plastics - wood and cigarette smoke - in the ground through leaks in storage tanks Effects - BP oil spill released benzene - Benzene can cause many cancers and disorders - Normal urban areas have benzene measurements from >1 to a little over 100 PPB(Parts Per Billion) - Gulf measurements at hundreds PPM(Parts Per Million) - Ways to remove benzene include activated charcoal, baking soda, bentonite clay, and using products that support your liver Benzene is... By Eann Diller Regulations Chemical Name: Benzene Molecular Formula: C6H6 Structural Formula: Common Name: Benzene Common Phase: Liquid Benzene In small doses, benzene can cause... - eye, skin, nose, and throat irritation - headache - vomiting - convulsions - Benzene use as a solvent was banned 20 years ago - Maximum amount of benzene in water is 0.005 milligrams per liter - FDA bans use of benzene in food Works Cited Benzene is used in... - adhesive produuction - painting - pesticide manufacturing - refinery workers - truck drivers Article "42 Common Toxic Chemicals and Their Effects ." www.mcsbeaconofhope.com. N.p.. Web. 6 Mar 2013. Isaacs, Tony. "Natural Help Removes Benzene and Other Harmful Gulf Oil Spill Toxins." www.naturalnews.com. N.p., 17 Sep 2010. Web. 6 Mar 2013. www.benzene.org. N.p., 21 Jul 2009. Web. 6 Mar 2013. <http://www.benzene.org/benzene-information.html>. - colorless hydrocarbon that has a sweet odor - evaporates quickly and slightly dissolves in water - occurs naturally in crude oil, volcanoes, and forest fires - can be found in some plants and animal species Chronic benzene exposure can cause... - leukemia - damage to blood cells - birth defects - damage to DNA
Transcript: Questions? Nitration of a benzene ring This mechanism DOES NOT show the H-D Isotope effect because the Hydrogen-Carbon bond is being broken in the fast step. HNO3 to make NO2+ (which acts as an electrophile) the mechanism: H2SO4 Conditions: by Cara McKinney
Transcript: Benzene Ring It has a six-carbon ring. Each of the carbons has sp2 hybridization. That gives it 120 degree bond angles all around the molecule. That makes it a perfect hexagon with a hydrogen atom sticking out from each point. Note that all these atoms are in the same plane. But that in itself is not what makes it special. Orbital diagram of benzene from top. If we turn the molecule on its side you can see that the sp2 hybridization leaves each carbon atom with one half-filled p orbital. Each of these forms pi bonds to neighbors on both sides, and the pi bonding goes all the way around the molecule. Orbital diagram of benzene from the side showing p-orbitals. For Kekule, benzene was a great challenge. He spent many years trying to work out the structure. Once, while thinking about the problem, he nodded off and had a day-dream. In it he saw a snake coil up, and suddenly grab its own tail. It then struck him that benzene might be a 'ring'. In a dream, Kekule saw a snake coil up, and grab its own tail. It struck him that benzene might be a 'ring'. Structures, pi bonds, singe bond, double bond, bond angle, hybrid structure, resonance energy, hexagonal ring, benzene. Biting one's own tail: the history of benzene What is benzene? Match the words with translation: Benzen Электронные облака orbitals Возбуждения электрона Aromatic compound Неспаренные электроны cyclic ring Двойная связь hexagonal form Температура плавления bond angle Температура кипения Double bond Гибридизированные орбитали Flammable liquid Угол связи Electron clouds Ненасыщенные соединения Valence bond Орбитали Unsaturated compounds Гексагональная форма Boiling temperature Исходное вещество для синтеза derivative Легковоспламеняющиеся жидкость Open chain Валентная связь Cyclic hydro carbon Производные Derivative Ароматический углеводород Excitation of electron Циклическое кольцо Hybridized orbitals Циклический гидракарбон Melting temperature Открытая цепь Umpaired electrons Исходное вещество для синтеза EXPERIENCE Teacher: Assilbekova H. N. Benzene Home work Work in pairs. Describe the structure of benzene. Exercises 3 1. A benzene molecule is a regular hexagonal structure with three ......... arranged in conjugated manner. 2. All the carbon-carbon bonds in benzene molecule are of equal bond length around 1.39 pm which is an intermediate value of carbon-carbon ............ (1.46 pm) and carbon -carbon ............... (1.34 pm) in hydrocarbons. 3. The molecule is a planer hexagonal geometry with the ........... of 120Â°. Sometime one structure of molecule cannot explain all the chemical properties of molecule, in such case more than one structure can be drawn for same molecule. 4. The difference between drawn structure and the resonance hybrid structure is known as ............. 5. For ............, there are two possible resonance structures given by Kekul and also called as Kekul structures. 6. Both resonating structure contains alternate double and single bonds and resonance hybrid shows with a ring in ............................... There are no individual localized pi bonds, just a big super pi bond. It is actually called a delocalized pi bond to distinguish it from the pi bonds that are localized alongside two carbon atoms to form the double and triple bonds that we dealt with earlier in this lesson. This super or delocalized pi bond is unusually stable. It will not react with bromine like the localized pi bond that is found in alkenes. Another way of saying this is that because the pi bond is not localized between, or associated with, just two carbon atoms, we have not really formed a double bond as such. Because of this, the electrons are not concentrated enough or available enough to react with the bromine. Orbital diagram of benzene showing pi bonding rings. [62orb14.JPG] This picture shows a close-up view of how the p orbitals overlap one another to form pi bonding all the way around the benzene molecule. The sigma bonds between adjacent carbon atoms are not shown in this picture. §7.8 Read the text Exercises 1 Exercises 2 Fill in the gaps with these words TERMS Kostanay State Pedagogical Institute Nature-mathematical faculty Benzene - organic compounds which are composed of carbon and hydrogen are called as hydrocarbons.The molecular formula of benzene is C6H6. Rubric 1. Benzene – Бензол 2. Open chain – открытая цепь 3. Сyclic hydrocarbon – циклическйий гидракарбон 4. cyclic ring – циклическое кольцо 5. aromatic compound – ароматический углеводород 6. double bond – двойная связь 7. derivative – производные 8. flammable liquid – легковоспламеняющиеся жидкость 9. precursor for a synthesis – исходное вещество для синтеза 10. hexagonal form – гексагональная форма 11. unsaturated compounds – ненасыщенные соединения 12. bond angle – угол связи 13. hybridized orbitals - гибридизированные орбитали 14. boiling temperature – температура кипения 15. melting temperature – температура плавления 16. valence bond – двойная связь 17. unpaired
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