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Lab Week 15-16: Gas Stoichiometry & Aspirin Synthesis Report

Complete your Chem 108 lab report on gas stoichiometry, weigh and calculate yield for aspirin synthesis. Turn in your report with clear calculations.

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Lab Week 15-16: Gas Stoichiometry & Aspirin Synthesis Report

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  1. Chem 108 LabWeek 15 16 • Pick up papers & pink Lab Equipment Inventory Sheet & Tag for Lab combination lock • Sit @ your original Lab Drawer Station

  2. Due Today: Chem 108: Lab Gas Stoichiometry Complete Report form pages pp. 58-60. (Individual) Include clear calculations with units.

  3. Aspirin Synthesis Complete and turn in today with clear calculations. • Experiment uses acetic anhydride (C4H6O3) Weigh aspirin, complete calculations and form. Dispose of aspirin in “crude” aspirin container

  4. Synthesis of Aspirin

  5. Representing Organic MoleculesCommon Formulas & Drawings Empirical Formula: Molecular formula: C7H16O C7H16O Condensed Structure: Bond-Line Structure:

  6. Mass Calculations: C7H6O3 C9H8O4 grams (Salicylic Acid) grams (Aspirin) Moles C9H8O4 MW = 180.15 Molar Mass Stoichiometry grams (A) (Molecular 1 mol (SA) 6.0 grams (SA) 1 mol A Weight A) ? (A) 1 mol SA grams (SA) 1 mol (A) 7.8 g aspirin (Molecular Weight SA) "Gatekeeper" C7H6O3MW = 138.12

  7. Percent Yield • Calculate the % Yield: actual yield (g) versus the theoretical calculated yield (g). • % Yield = actual (g) / theoretical (g) x 100 Weigh crude aspirin & calculate % yield. Turn in individual Report Form with partner’s name(s).

  8. Chem 108Synthesis of Aspirin Due Today Weigh Aspirin Calculate % Yield Report Form Due Today

  9. Report Form due Today Post Lab Questions Due on-line Friday December 14th. http://chemconnections.org/general/chem108/Aspirin%20Guide.html

  10. Anonymous End of Course Survey • Available • End of course anonymous survey: Due. • Full Quiz Credit provided on completion. • Go to https://salgsite.net/student • * Fill in your email address • * Enter the instrument number: * Provide the instrument password: chem108

  11. Check in lab drawer Chem 108: Class/ Lab Week 16 (Return any loaned i-clickers) Check that you have everything on the pink inventory sheet: clean & not broken; dispose of any broken glass in the broken glass container. Replace the paper @ the bottom of the drawer with clean paper towel. Note any missing equipment on the pink sheet., then replace all equipment in the drawer. Take a tag, write the combination number on the tag & fasten to lock. Write your name on the blackboard. Dr. R. will check pink sheet & sign off. This completes your semester in Chem 108. Thank you, and best wishes.

  12. Organic Molecules Tutorial Functional Groups Dr. Ron Rusay

  13. Functional Groups & Amino Acids

  14. Elemental building blocks for all organic molecules

  15. Synthesis of a Non-steroid anti-inflammatory drugAspirin http://chemconnections.org/general/movies/Representations.MOV

  16. QUESTION #1 One of aspirin’s functions, an ester, is circled in blue. What is the highlighted yellow function?: Alcohol Ether Ketone Aldehyde Carboxylic Acid

  17. Answer #1 One of the functions, an ester, is circled in blue. What is the highlighted yellow function?: Alcohol Ether Ketone Aldehyde Carboxylic Acid

  18. Salicylic Acid Common Functional Groups NameGeneral Formula Alcohols R Ethers RR Amines RNH2 Carboxylic Acids

  19. Aspirin Common Functional Groups NameGeneral Formula Aldehydes Ketones Carboxylic Acids Esters Amides

  20. Shapes, Functions & Structural AnalogiesWater, Ammonia, MethanePlus C=O “carbonyls” Organic Molecules

  21. Molecular Models for C, H, N, O Fundamental repeating shapes found in every biological molecule • C =black • H = gray • N = blue • O = oxygen • pink = generic atom

  22. Representing Organic Molecules http://chemconnections.org/general/movies/Representations.MOV

  23. Representing Organic MoleculesCommon Formulas & Drawings Empirical Formula: Molecular formula: C7H16O C7H16O Condensed Structure: Bond-Line Structure:

  24. QUESTION #2 A compound that smells like fresh raspberries, the following structure, C?H?O?, matches its calculated molar mass which is 164 g/mol. A) TRUE B) FALSE

  25. Answer #2 A compound that smells like fresh raspberries, the following structure, C?H?O?, matches its calculated molar mass which is 164 g/mol. A) TRUE B) FALSE C10H12O2, matches its calculated molar mass which is 164 g/mol.

  26. Organic Molecules Common Functional Groups NameGeneral Formula Alcohols R Ethers RR Amines RNH2 Carboxylic Acids R or R represents any generic carbon atom bonded in the functional group

  27. Organic Molecules Common Functional Groups NameGeneral Formula Aldehydes Ketones Carboxylic Acids Esters Amides R or R represents any generic carbon atom bonded in the functional group

  28. QUESTION #3 Select the function(s) in the molecule

  29. Answer #3 Select the function(s) in the molecule X X

  30. Detecting stuff we cannot see: the Sense of Smell Models, Theories & Interactions http://chemconnections.org/organic/chem226/Labs/Smell/smell-links.html Structure-Odor Relationships Karen J. Rossiter, Chem. Rev., 1996, 96, 3201-3240

  31. Historical view of a few smell receptors. 4 October 2004 The Nobel Assembly at Karolinska Institutet has today decided to award The Nobel Prize in Physiology or Medicine for 2004 jointly to Richard Axel and Linda B. Buck for their discoveries of "odorant receptors and the organization of the olfactory system" http://chemconnections.org/organic/chem226/Labs/Smell/ChemComm.html

  32. Organic Functions & Smell Receptors.

  33. One molecule, one function: One Smell Receptor Isoamyl acetate, also known as isopentyl acetate, is formed from isoamyl alcohol and acetic acid. It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is also described as similar to both banana and pear.[3] Banana oil may be either pure isoamyl acetate, or flavorings that are mixtures of isoamyl acetate, amyl acetate, and other flavors. C7H14O2

  34. One molecule among 82 primary chemicals found in bananas: C7H14O2

  35. QUESTION #4 C7H14O2 The function in isoamyl acetate’s structure is a(n): Alcohol Aldehyde Ketone Ester Carboxylic Acid

  36. Answer #4 C7H14O2 The function in isoamyl acetate’s structure is a(n): Alcohol Aldehyde Ketone Ester Carboxylic Acid

  37. One molecule, two functions: One Smell Receptor Methyl salicylate (oil of wintergreen or wintergreen oil) is naturally produced by many species of plants, particularly wintergreens. It is also synthetically produced, used as a fragrance, in foods and beverages, and in liniments. C8H8O3

  38. QUESTION #5 C8H8O3 One of the functions, an ester, is circled. What is the other function?: Alcohol Ether Ketone Aldehyde Carboxylic Acid

  39. Answer #5 C8H8O3 One of the functions, an ester, is circled. What is the other function?: Alcohol Ether Ketone Aldehyde Carboxylic Acid

  40. One molecule, three functions: One Smell Receptor Vanillin An extract of the cured, full-grown, unripe fruit of an orchid produces a popular flavoring. The natural extract sells for ~ $1500/kg versus ~ $20/kg for the synthetic version. The structure of the compound that is responsible for the smell/flavor is shown to the right. The Guinness Book of World Records once listed this compound as having the lowest smell detection limit of all chemicals (2 x 10 –11 g per 1,000 cm3 of air). Bonus: The space (volume) of the Oakland Coliseum Arena, aka Oracle Arena, is approximately 90,000,000 ft3. If 1.00g of the compound were released at center court, and was completely and evenly dispersed throughout the building, would you smell it sitting in sec. 204, row H, seat 121? Show your calculation. (1 ft3 = 0.0283 m3)

  41. QUESTION #6 Vanillin One of the functions, an alcohol, is circled. What are the other two functions?: Aldehyde + Ketone Carboxylic Acid + Ester Ketone + Ether Aldehyde + Ether Carboxylic Acid + Aldehyde

  42. Answer #6 Aldehyde Ether Vanillin Aldehyde Ether One of the functions, an alcohol, is circled in blue. What are the other two functions?: Aldehyde + Ketone Carboxylic Acid + Ester Ketone + Ether Aldehyde + Ether Carboxylic Acid + Aldehyde

  43. What a smell looks like https://www.youtube.com/watch?v=58U52lDTuvk&list=PLgawtcOBBjr9I-NDoUX-HmTQr_VN465G2&index=3

  44. Inside the extraordinary nose of a search-and-rescue dog https://www.youtube.com/watch?v=FLH36ML8IEU

  45. Dogs Can Smell Cancer - Secret Life of Dogs - BBC https://www.youtube.com/watch?v=e0UK6kkS0_M

  46. Mass Calculations: Reactants Products • How many grams of aspirin are theoretically produced from 6.0 g of salicylic acid with an excess of acetyl chloride, C2H3OCl? • Balanced Equation: 1 1 1 1

  47. Mass Calculations: Reactant Product • How many grams of aspirin are theoretically produced from 6.0 g of salicylic acid with an excess of acetyl chloride, C2H3OCl? • Balanced Equation: 1 1 1

  48. Mass Calculations: Reactants Products

  49. Theoretical (Yield) Mass Calculations Reactant Product grams (Reactant) grams (Product) Moles Molar Mass Stoichiometry grams (P) 1 mol (R) grams (R) ? mol (P) ? grams (P) ? mol (R) grams (R) 1 mol (P) (Divide) Mass (R) (Multiply) Mass (P) by Molar "Gatekeepers” from Balanced reaction by Molar

  50. Mass Calculations: A SA grams (Salicylic Acid) grams (Aspirin) Moles C9H8O4 MW = 180.15 Molar Mass Stoichiometry grams (A) (Molecular 1 mol (SA) 6.0 grams (SA) 1 mol A Weight A) ? (A) 1 mol SA grams (SA) 1 mol (A) 7.8 g aspirin (Molecular Weight SA) "Gatekeeper" C7H6O3MW = 138.12

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