2. Sense-able Smells Making Organic Structures Accessible for High School Andro Rios and Gerald French Bio-Bridge Pilot Training Session Copyrighted All Rights Reserved

3. 2004 Nobel Prize in Physiology or Medicine “ for their discoveries in odorant receptors and the organization of the olfactory system” Linda Buck Fred Hutchinson Cancer Research Center Seattle, WA, USA Richard Axel Columbia University New York, NY, USA Our Sense of Smell http://nobelprize.org/nobel_prizes/medicine/laureates/2004/illpres/ Nobel Prize 2004 Website

4. How do we Smell? http://nobelprize.org/nobel_prizes/medicine/laureates/2004/illpres/ Odorant molecules can serve as sources of engagement!!

5. Physics BiologyEarth Sciences Astronomy Chemistry A significant barrier to overcome

6. Why introduce bond line organic structures? They highlight only the important parts of a molecule They are easier to use for discovering patterns To directly address the “intimidation factor” Scientists use this language, why not students of science? Compare and Contrast

7. What is the unifying pattern in amino acids? Consider two structural versions

8. Activity Objectives 1. To demonstrate the everyday role of organic molecules. 2. To make molecular structures less intimidating. 3. To provide students with the opportunity to make their own observations and conclusions. 4. To empower students with the skills to engage in other activities relating to bio-molecules.

9. Are you hypersensitive to common odors or fragrances? While these odors are considered pleasant and safe, there are many people who suffer severe irritation even from the most common and mild odors/aromas. If you are one of these individuals, you should not participate in this activity.

10. Before you begin….…….. For each sample, first try wafting, because some odors are stronger than others. If you still can’t smell anything, bring the sample closer to your nose.

11. Part A. Aldehydes Molecular StructureDescription and association of odor Odor identification Part A. Fill out this table as you go about wafting the odors from the three samples Odor 1 Odor 2 Odor 3

12. Aldehydes Part A. Compare and Contrast: All aldehydes seem to have this in common: Odor 1Odor 2Odor 3 Molecule 4

13. The Aldehyde Odors Odor 1 Vanilla Odor 2 Cinnamon Odor 3 Almonds or Cherries

14. Part B. Esters Molecular StructureDescription and association of odor Odor identification Part A. Fill out this table as you go about wafting the odors from the three samples Odor 4 Odor 5 Odor 6

15. Esters Part B. Compare and Contrast again All esters seem to have this in common: Odor 4Odor 5Odor 6

16. Esters Part B. 1.How many carbon and hydrogen atoms do you see in the short-hand version of Odor 4? one C atom and two H atoms 2. How many carbon and hydrogen atoms do you see in the full atom version? eight C atoms and eight H atoms 3.In comparing the short hand and full atom version, what does the number 3 on the H 3 refer to in the short-hand version? Indicates there are three hydrogen atoms 4. Oxygen atoms are easy to spot since they are always shown in both the short-hand and full atom versions. How many oxygen atoms are in Odor 4? __3__

17. Esters Part B. Slide 2 5.Using the Full atom version circle the parts on it that are visible in the short hand version. 6.Using the short-hand version, fill in the missing atoms on it that are shown in the full atom version. 4. Oxygen atoms are easy to spot since they are always shown in both the short-hand and full atom versions. How many oxygen atoms are in Odor 4? three O atoms Compare the two versions of Odor 5 then answer these related questions:

18. Esters Part B. slide 3 8.How many carbon atoms are in odor 6 total? Now look at the Odor 6 molecule (shown below). Draw in the symbol for carbon for the missing carbons atoms on the molecule. seven C atoms 7. Describe and illustrate how you think the missing carbon atoms are represented in the short-hand version: At the points where lines meet(a vertex), or other joining of multiple lines, is where the missing carbon atoms are found.

19. The Ester Odors Odor 4 Wintergreen Odor 5 Pineapple Odor 6 Banana

20. Part C. Terpenes Molecular StructureDescription and association of odor Odor identification Part A. Fill out this table as you go about wafting the odors from the three samples Odor 7 Odor 8 Odor 9

21. Terpenes Part C. Compare and Contrast All terpenes seem to have this in common: Odor 7Odor 8Odor 9

22. 1.Did you observe that two of the terpene odors smelled similar? 2.Can you provide a reason based on the molecular structures shown below as to why two of them smelled similar? Odor 7Odor 8 Terpenes Part C. slide 2 Odor 9

23. Odor 7 Odor 9 Can you find all 10 of the carbon atoms in Odor 7 and Odor 9 (shown below)? Three of them are easy to find, but can you find the other seven which are the not drawn in on the short-hand version. Circle all 10 carbon atoms for each molecule. Terpenes Part C. slide 3

24. The Terpene Odors Odor 7 Orange Odor 8 Lemon Odor 9 Pine / Pine needles

25. Part D. Alcohols Molecular StructureDescription and association of odor Odor identification Part A. Fill out this table as you go about wafting the odors from the three samples Odor 10 Odor 11 Odor 12

26. Alcohols Part D. Compare and Contrast All alcohols seem to have this in common: Odor 10Odor 11Odor 12

27. Alcohols Part D. slide 2 1.No matter which carbon atom you look at in the Full atom version, how many lines are connected to it? 2.If the letters (C, H and O) in Odor 10, or any molecule you have smelled today, represent atoms in a molecule, what might the lines connecting the letters represent? The short-hand and full atom version of Odor 10 is shown below. Answer the following questions relating to the structures. Always four lines. They represent the chemical bonds between atoms in a molecule.

28. Alcohols Part D. slide 3 Hypothesis: Shown below are two short-hand versions of Odor 10, the one on the right includes all of the hydrogen atoms. Look at the arrows pointing at two different carbon atoms in the representation on the left. Observe in the representation on the right that each of those carbon atoms has a different amount of hydrogen atoms bonded to it. Look for a pattern and provide a reason why you think this happens? Each vertex needs four lines. If there are less than four lines at a vertex, then lines with an ‘H’ are added until the vertex has a total of four lines. Hint: Question 1 provides a strong clue…… Each carbon atom needs four bonds. If there are less than four bonds at a carbon atom, then hydrogens are added until the carbon atoms has four bonds.

29. Alcohols Odor 10 Rose Odor 11 Thyme Odor 12 Peppermint

30. Part E. Ketones Molecular StructureDescription and association of odor Odor identification Part A. Fill out this table as you go about wafting the odors from the three samples Odor 13 Odor 14 Odor 15

31. Ketones Part E. Compare and Contrast Odor 13Odor 14 Odor 15 All ketones seem to have this in common:

32. Ketones Part E. 2. How many carbon atoms does it have? 3. How many oxygen atoms does it have? 4. How many hydrogen atoms does it have? Odor 13 1.Circle all of the carbon atoms in Odor 13 Eleven C atoms three O atoms fourteen H atoms

33. Ketones Part E. slide 3 5. Draw the full-atom version of odor 13 in the box below Full atom version of Odor 13

34. Ketones Part E. slide 4 6. Circle in all of the carbon atoms in odor 14 shown below on the left. Then determine which carbon atoms need hydrogen atoms and draw them in on the structure on the right.

35. Ketones Odor 13 Ginger Odor 14 Spearmint Odor 15 Caraway

36. Ketone Station Odor 13Odor 14 Spearmint Odor 15 Caraway Cedar