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Sensable Smells: The Chemistry of Fragrances

Procedure and Analysis
Use the PowerPoint presentation as a guide to explore the organic structures that represent a variety of fragrances and respond to the tasks as you proceed.

Part A: Aldehydes Odor 1 Molecule Odor 2 Odor 3

Smell Prediction
(Try to identify the smell)

Actual Smell 1. Each of the molecules in Part A has a different odor. Explain why. 2. Aldehydes are a family of organic molecules, because they all share common bonding patterns. Study the 3 molecules in Part A. What is the unifying pattern that makes each of these molecules an aldehyde. Draw it at the right.

Part B: EstersUnderstanding what the structures represent

Odor 4 Odor 5 Odor 6

Molecule

Smell Prediction
(Try to identify the smell)

Actual Smell 1. Odors 4, 5, and 6 belong to the family of molecules called esters. Find the common pattern within the family of esters and draw it at the right.

Modified from Sensable Smells authored by Andro Rios, UCSD Organic Chemistry Department, and Teacher Partner Gerald Finch, Montgomery High School, Chula Vista. Developed during NSF-funded GK-12 UCSD Socrates Fellowship and published July 2011 ACS. Permission to distribute granted.

Name 2. Most organic molecules are largely made of carbon (C) and hydrogen (H) atoms. Because of this, it is often distracting to draw every carbon and hydrogen atom in a molecular structure. Therefore, scientists often draw the organic molecules in a shorthand version where the carbon atoms are inferred where 2 lines meet. Example: Shown below is the molecule for Odor 4 in its short-hand version and in its full atom version. Study the 2 representations and answer the following questions. a. How many carbon atoms and hydrogen atoms do you see in the short-hand version of Odor 4? b. How many carbon atoms and hydrogen atoms do you see in the full atom version of Odor 4? c. Compare the 2 versions of Odor 4. What does the number 3 on the H3 mean in the shorthand version? d. Oxygen atoms are shown in both versions. How many oxygen atoms are in Odor 4? a. Using the full atom version, circle the parts that are also visible in the short-hand version. C=

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H=

3. Compare the 2 versions of Odor 5 shown below and answer the related questions on the right.

4. Refer to the Odor 6 molecule. Write the element symbol for carbon for the ones that are not shown.

b. Using the short-hand version, fill in the missing atoms that are shown on the full atom version. c. Describe and illustrate how are carbon atoms represented in the short-hand version? a.

b. How many carbon atoms comprise Odor 6?

Modified from Sensable Smells authored by Andro Rios, UCSD Organic Chemistry Department, and Teacher Partner Gerald Finch, Montgomery High School, Chula Vista. Developed during NSF-funded GK-12 UCSD Socrates Fellowship and published July 2011 ACS. Permission to distribute granted.

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Part C: TerpenesDiscovering similar smells and finding atoms

Odor 7 Odor 8 Odor 9

Molecule

Smell Prediction
(Try to identify the smell)

Actual Smell 1. Odors 7, 8, and 9 comprise the family of molecules called terpenes. Identify the common pattern within the family of terpenes and draw it to the right.

2. Compare Odor 7 and Odor 8. Explain why they might have similar smells. Two compounds with the same molecular formula (same atoms) but with different structures are called isomers. Odor 7 and Odor 8 are sterioisomers meaning they are arranged as mirror images of each other. For example, your right hand and left hand both have 4 fingers and a thumb but are mirror images. These sterioisomers react with your olfactory receptors differently. 3. Find and circle all 10 carbon atoms in Odor 7 and Odor 9.

Part D: Alcohols
Odor 10 Molecule Odor 11 Odor 12

Smell Prediction
(Try to identify the smell)

Modified from Sensable Smells authored by Andro Rios, UCSD Organic Chemistry Department, and Teacher Partner Gerald Finch, Montgomery High School, Chula Vista. Developed during NSF-funded GK-12 UCSD Socrates Fellowship and published July 2011 ACS. Permission to distribute granted.

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1. Odors 10, 11, and 12 comprise the family of molecules called alcohols. Identify the common pattern within the family of alcohols and draw it at the right. 2. The short-hand and full atom version of Odor 10 is shown. Answer the questions related to the structures at the right.

a. Refer to the full atom version for Odor 10. How many lines are connected to every carbon (C) atom? b. How many lines are connected to each oxygen atom (O)? c. How many lines are connected to each hydrogen atom (H)?

3. Molecular structures would not exist without the valence electrons that are available for bonding. Draw the Lewis dot structures carbon, hydrogen, and oxygen. 4. How are unpaired electrons in a Lewis dot structure similar to the lines that are shown to connect 2 atoms in a molecular structure? 5. The atoms that comprise the molecular structures in this lab are carbon, hydrogen, and oxygen atoms. Therefore, what type of chemical bonds hold the atoms together? Ionic? Covalent? 6. Shown below are two short-hand versions of Odor 10. The one on the right includes all 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?

Modified from Sensable Smells authored by Andro Rios, UCSD Organic Chemistry Department, and Teacher Partner Gerald Finch, Montgomery High School, Chula Vista. Developed during NSF-funded GK-12 UCSD Socrates Fellowship and published July 2011 ACS. Permission to distribute granted.

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Part E: KetonesAssessing what you have learned

Odor 13 Odor 14 Odor 15

Molecule

Smell Prediction
(Try to identify the smell)

Actual Smell 1. Odors 13, 14, and 15 comprise the family of molecules called ketones. Identify the common pattern within the family of ketones and draw it at the right. 2. Circle all the carbon atoms in Odor 13 below.

a. How many carbon atoms does it have? b. How many oxygen atoms does it have? c. How many hydrogen atoms does it have?

3. Draw the full-atom version of Odor 13 in the space at the right. Refer back to your previous work to help you.

4. Circle all of the carbon atoms in odor 14. Then, determine which carbon atoms need hydrogen atoms and draw them in on the structure at the right.

Modified from Sensable Smells authored by Andro Rios, UCSD Organic Chemistry Department, and Teacher Partner Gerald Finch, Montgomery High School, Chula Vista. Developed during NSF-funded GK-12 UCSD Socrates Fellowship and published July 2011 ACS. Permission to distribute granted.