SCH4U Lee 2.1

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OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05) Ottawa-Carleton Virtual Secondary School 2020-2021 Mr. Daniel Cho-En Lee ( daniel.cho-en.lee@ocdsb.ca ) Unit 2: Organic Chemistry “Common knowledge” Kahoot! In the food industry, “organic” means the product involves no synthetic fertilizers or pesticides. “Organic” means “related to life .” Whether an organic food actually contains more nutrition or less harmful substances depends on each product. In the beginning, organic compounds were believed to be produced only by naturally occurring living organisms. Starting with urea, more and more organic compounds can be synthesized. Now, organic compounds means carbon-based compounds (which very likely also contain H ), which are characteristic to life on Earth. Earth’s crust is not particularly carbon-rich (0.2%), but about half of living organism’s dry mass is carbon. There are two reasons why carbon is so life-friendly. (1) Carbon makes up to 4 bonds. It is capable of making tetrahedral, trigonal planar, and linear shapes. (2) Adequate bond (dissociation) energy. Carbon is small enough so that its bonds do not break easily. It also has a medium electronegativity , so that it does not form hard-to-break ionic bonds with elements on the other end of the electronegativity spectrum. Carbon bonds with a variety of elements. These two properties make carbon a versatile building block. Many carbon-based organic compounds are therefore large and complex. Exercise 0 : Oxygen is the most abundant element in Earth’s crust. Why is oxygen not the best building block for life? Only 2 bonds; forms ionic compounds that are too hard to break Extended topic: Are there silicon-based life? 1
OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05) Ottawa-Carleton Virtual Secondary School 2020-2021 Mr. Daniel Cho-En Lee ( daniel.cho-en.lee@ocdsb.ca ) https://www.youtube.com/watch?v=fQCrrPohyts Hydrocarbons - Alkane (suffix: -ane ) Hydrocarbons (H & C, nothing else) are the simplest type of organic compounds. And the simplest type of hydrocarbons are alkanes (all names of alkane ends with -ane), which is solely made of sp 3 carbon saturated with hydrogen. Alkanes have the chemical formula of C n H 2n+2 (the “+2” H are attached to the C and both ends). Prefix (# of carbon in the main chain) 1 2 3 4 5 6 7 8 9 10 meth- eth- prop- but- pent- hex- hept- oct- non- dec- Please use 2 minutes to memorize this list. We will play a Kahoot game! Exercise 1 . What should we call C 6 H 14 ? hexane Exercise 2. There may be one or more carbon side chains on a hydrocarbon. Draw one C 6 H 14 that includes a carbon branch - a side chain . If you have a molecular model building kit, build one. How to draw: There are four frequently-seen ways to draw an organic compound: (a) molecular/chemical formula (C 6 H 14 ), (b) condensed structural diagram, (c) line diagram, and (d) full structural diagram. Please draw all of them for your side-chained C 6 H 14 . It turns out there are five possible C 6 H 14 . The straight chain hexane is n- hexane ( n = normal). The other four are: 2- meth yl pentane , 3- meth yl pentane , 2,3- di meth yl butane , and 2,2- di meth yl butane . Can you see the naming pattern here? If the side chain grows on the second carbon of the main chain, add “ 2- ” before the side chain. 2
OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05) Ottawa-Carleton Virtual Secondary School 2020-2021 Mr. Daniel Cho-En Lee ( daniel.cho-en.lee@ocdsb.ca ) # of the same functional group on a side chain: 2 = di -, 3 = tri -, 4 = tetra - Length of carbon chain in the functional group: 1 = meth yl , 2 = eth yl , 3 = prop yl , 4 = but yl IUPAC (International Union of Pure and Applied Chemistry) is the agency that makes the rules of nomenclature. In this course we will learn several key naming principles. Besides the three rules above, please know that: (1) The longest continuous carbon chain is the main chain. (2) Minimize numbers. 2,2-dimethylbutane is better than 3,3-dimethylbutane. See Google slide for more explanation: https://docs.google.com/presentation/d/1HoLRrlCGU5k-OcGFjVr5cMPsshc5ag6j48uNzueUujU/edit?usp=sharing Exercise 3 . Name as many different C 5 H 12 as you can. (Try to rotate them to see if two apparently different compounds are actually the same.) n-pentane, 2-methylbutane, 2,2-dimethylpropane Finally, name the alkane on the right: 2,2,3,3-tetramethylbutane Isomers You have learned isotopes - same element (same number of protons) but with different numbers of neutrons. Many complex organic compounds have isomers , which share the same chemical formula (e.g. C 6 H 14 ) but are structurally different. We just found out that C 6 H 14 has 5 isomers and C 5 H 12 has 3. Let’s appreciate the number of isomers for different alkanes. https://i.stack.imgur.com/kAbs7.jpg Exercise 4 . Name two isomers of the 8-carbon compound in exercise 3. How many isomers does it have? 3,4-dimethylhexane, 2,2-dimethylhexane Properties of Alkanes Under room temperature (25°C) and 1 atm, methane, ethane, propane, and butane exist as gas. These make up natural gas (the C comes from anaerobically decomposed organisms and 100+ million-year-old organic compounds), in which 3
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OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05) Ottawa-Carleton Virtual Secondary School 2020-2021 Mr. Daniel Cho-En Lee ( daniel.cho-en.lee@ocdsb.ca ) methane is roughly 80% of the mixture. Natural gas is responsible for winter heating in cities. Propane is commonly compressed and sold as a liquid. Alkanes are highly non-polar because all carbons are saturated by weakly δ + hydrogen. Larger alkanes have more intermolecular attractions (induced transient dipole-dipole) among molecules, so that they are normally liquids or solids. (Gravity is far weaker than electrostatic attractions at the atomic scale, so we can safely ignore the fact that large alkanes are also “heavier.”) Exercise 6: Which of the following alkanes are liquid at room temperature, 1 atm? (a) C 4 H 10 (b) C 8 H 18 (c) C 12 H 26 (d) C 100 H 202 Methane is a potent greenhouse gas due to its four C-H bonds to absorb infrared rays in the atmosphere. (The bonds will vibrate more as a result.) The global emission of methane is rising rapidly, contributing increasingly more significantly to global warming. The livestock industry and the fossil fuel industry are the largest methane emitters. Extended topics Kurzgesagt - In a Nutshell: Fracking explained https://www.youtube.com/watch?v=Uti2niW2BRA Seeker: Onions Could Stop Cows From Farting The Planet To Death https://www.youtube.com/watch?v=oH79CGm4u7s Alkenes (suffix: -ene ) Alkenes are alkanes with one or more double bonded carbon. Their IUPAC names end with -ene. The simplest alkene is ethene (old name: ethylene), C 2 H 4 . Compared to alkanes, each double bond in an alkene takes the place of two bonded H. If there is only one double bond, the alkene has an easy chemical formula of C n H 2n . If there are two double bonds, the chemical formula becomes C n H 2n-2 , and so on. 4
OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05) Ottawa-Carleton Virtual Secondary School 2020-2021 Mr. Daniel Cho-En Lee ( daniel.cho-en.lee@ocdsb.ca ) The name “butene” above is confusing. Please include the location of the double bond within the name, just before the -ene, such as but -1- ene and but -2- ene (old: 1-butene, 2-butene). Use the first carbon on the main chain where the double bond begins. but a -1,3- di ene prop a di ene If there are two double bonds, both carbons should be named. The suffix becomes di ene. Exercise 7. Draw the line diagrams of a hex-1-ene, a hex-2-ene, and finally a 2,3- di methylbut-2-ene. Recall that sp 2 bond hybridization produces flat molecules as atoms are coplanar (on the same plane). A double bond cannot rotate because the π bond repels the sp 2 bonds. (On the other hand, a single bond can be rotated freely.) It turns out that there are two isomers of but-2-ene. There are two systems to distinguish these two isomers. (1) cis -but-2-ene, cis = the larger functional groups are on the same side of the double bond trans -but-2-ene, trans = on opposite sides (2) (Z) but-2-ene, Z - same side (E) but-2-ene, E - opposite sides This system is preferred when there are multiple double bonds (2E, 4Z, etc.) Exercise 8 . Return to the hex-1-ene you drew. Does hex-1-ene have cis/trans (E/Z) isomers? Why (not)? No. Both groups from the #1 carbon are hydrogen. More practice for cis(Z) / trans(E): 5
OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05) Ottawa-Carleton Virtual Secondary School 2020-2021 Mr. Daniel Cho-En Lee ( daniel.cho-en.lee@ocdsb.ca ) https://docs.google.com/presentation/d/1HoLRrlCGU5k-OcGFjVr5cMPsshc5ag6j48uNzueUujU/edit?usp=sharing Exercise 9. Name two different cis(Z) / trans(E) isomers of oct-2-ene. Supply the line diagram of each. Supply its chemical formula. cis -oct-2-ene, trans -oct-2-ene, (Z) oct-2-ene or (2Z) oct-2-ene, (E) oct-2-ene or (2E) oct-2-ene C 8 H 16 Exercise 10. Does 2,3- di methylbut-2-ene have cis/trans (E/Z) isomers? Why (not)? No, all groups coming out from the double bond are identical (-CH 3 ). Exercise 11 . Name these two compounds. 1. Longest continuous carbon chain - 5 carbons, so it is a pentane 2. Has a double bond. Minimize number, so it is a pent-2-ene (old: 2-pentene) 3. Has a methyl (1 C) side chain at #4 carbon on the mainchain, so it is 4-methylpent-2-ene 4. Left is (Z) 4-methylpent-2-ene; right is (E) 4-methylpent-2-ene Cis-fat vs. trans-fat A fat molecule contains one relatively polar “head” and three highly non-polar hydrocarbon “tails.” The hydrocarbon tail is either an alkane, a carbon chain saturated with hydrogen , or an alkene, a carbon chain with one or more double bonds. Fats that contain an alkene tail are unsaturated (with hydrogen). Since each single bond can be rotated to fit in an empty space, saturated fats pack quite tightly and generate a significant amount of intermolecular attractions. The melting point of saturated fat is higher than room temperature. 6
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OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05) Ottawa-Carleton Virtual Secondary School 2020-2021 Mr. Daniel Cho-En Lee ( daniel.cho-en.lee@ocdsb.ca ) Land animal fats are rich in saturated fat. For the past several decades, people have been speculating that ingested saturated fat, during transportation in the blood vessel, could deposit within the blood vessel wall and narrow it. Eventually the blood flow is blocked. If the coronary artery is blocked, the person suffers from heart attack. If an important artery to the head is blocked (or ruptures), the person suffers from stroke. Heart attack and stroke are among the most common causes of deaths in an industrialized society. (Cancer is the other top-3.) As for unsaturated fat, there are cis- and trans- isomers. A cis- isomer introduces a rigid “bent” within the tail. The extra space reduces intermolecular attraction so that cis-unsaturated fat is liquid at a lower temperature. Most vegetable oil and fish oil contain a high amount of cis-fat. Trans-fats are byproducts of the food processing industry, which passes H 2 to unsaturated fat to saturate it (so that the product does not drip liquid oil). The trans-isomer has the main chain on opposite ends of the double bond, which again enables tight packing and increases intermolecular attraction. However, the human body has not evolved an enzyme to process trans-unsaturated fat. Trans-fats therefore remain in our blood vessel for a longer period. Ingested trans-fat stays in the blood vessel and the person has increased risk of heart attack and stroke. Watch : AsapScience: Butter vs. Margarine https://youtu.be/KG_ybdk1VaE Exercise 12. During the break, examine a couple of nutrition labels on your household food products. Look for “trans 7
OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05) Ottawa-Carleton Virtual Secondary School 2020-2021 Mr. Daniel Cho-En Lee ( daniel.cho-en.lee@ocdsb.ca ) fat content” and “hydrogenated oil” in the ingredients. Hydrogenation reaction: alkene → alkane In grade-school science labs we have been working on relatively fast reactions. Slow reactions, such as the hydrogenation reaction of alkene to make alkane, require a catalyst. Let’s watch: https://youtu.be/R27PkAWqSTc Extended topic : Fruit ripening experiment with ethene https://www.youtube.com/watch?v=jzjBAAv9nxc Kahoot! 8