Synthesis of a Fruity Fragrance and Analysis by Gas Chromatography-Mass Spectrometry

The Question of the Day: How does temperature affect the yield of a chemical reaction? Introduction: After studying organic chemistry for the past semester, you have gained an understanding of the importance of organic compounds in our daily lives. This lab is meant to increase your synthetic lab skills, critical thinking, and problem solving capabilities when utilizing instrumentation techniques. Each group will synthesize banana fragrance at different temperatures and determine the optimum temperature required to get the maximum yield. Another fruity fragrance of your choice will also be synthesized. The purity of all the final products will be examined utilizing the GC-MS. Pre-lab Questions: Collaborative work (type the answers.) 1. 2. Do you expect the smell of the fruit and the skin to be the same? How can you prove this experimentally (without smelling)? In general, what class of compounds is responsible for the smell of the fruits? Give examples for the structures of these compounds in two fruits (banana and one other fruit). How many peaks do you expect to see in the GC-MS after your synthesis? (Hypothesis #1) How would you synthesize the compounds you selected for question 2 in an organic lab? Give the list of reagents needed for each one. Give the chemical data table for the reagents (identified in question 4) needed, as you have done for other experiments. Write the general mechanism for the reaction you are planning to perform in the lab. Do you expect variable yields for the banana-scented compound if the temperatures maintained are different? (Hypothesis #2) Give a brief description of Gas Chromatography-Mass Spectrometry (GC-MS). What are some applications for GC-MS?

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Safety: Remember, never directly smell a chemical; instead, waft the vapors. chemical. ever taste a

1st Day of the lab: Gas Chromatography/Mass Spectrometry Lab You will need to design an experimental procedure (macro-scale) to synthesize your favorite fruity fragrance. Submit a detailed procedure to your lab instructor before your scheduled lab. You may use the following reference for GC-MS: http://www.scientific.org/tutorials/articles/gcms.html Each group of two students will synthesize banana fragrance at different temperatures (to be assigned the day of the lab) and one other fruit fragrance of their choice. Copy and fill in the following table in your notebook.
Name of Ester Molecular formula Structural formula Molar mass density BP (C) Fragrance

Apple Banana Cherry Grape Orange Pear Peach Pineapple Raspberry

Discuss the following questions with your partner and submit the answers next lab period. In Lab Questions: Collaborative work (type the answers.) 1. 2. 3. 4. 5. Write the structure of your fragrant compounds from both syntheses. How could you determine the purity of the product? Give all the methods you know. Which may be the best method among the ones you have chosen and why? Suggest a procedure for purifying the products of your synthesis. Suggest a procedure for extracting the fruity flavor compound from your selected fruit.

Homework: Collaborative work Find and print the mass spectrum of each of your reactants and expected product by searching http://webbook.nist.gov/chemistry/name-ser.html

2nd Day of the lab: Gas Chromatography-Mass Spectrometry Lab You should review the GC-MS simulation software available in the Learning Resource Center (see handout on the last page for instructions). Use GC-MS to analyze the products you have synthesized. Identify peak(s) using the NIST library search, and compare mass spectra of your products to the mass spectra you obtained from the NIST website. Discuss the following questions with your partner and submit the answers with your final report. Post-Lab Questions: Collaborative work (type the answers.) 1. 2. 3. 4. Is your banana scented compound pure? If not, why? Was your hypothesis #1 for the number of peaks seen in the GC-MS (number of products synthesized) correct? If not, what was the cause of the different number of peaks? Is your hypothesis #2 about temperature dependence of the esterification correct? If not, why? (You will need to review the results from the other teams.) Propose a method USDA can use to identify the adulteration in artificial flavors marketed in United States.

Post Lab Report: Collaborative work Prepare your report in a format suitable for submittal to an ACS journal (such as the Journal of Organic Chemistry). You may find it helpful to look at some examples on the following website: http://pubs.acs.org/

Acknowledgements The development of this laboratory experiment was supported by a grant from the National Science Foundation, through the Course, Curriculum, and Laboratory Improvement Grant #0633646 to Pennsylvania State University - Altoona College.

Instructions for using the GC-MS Software in Learning Resource Center 1. Log onto the computer that has the GC-MS Software (Savant) label on it (of the three in the main lobby of the Learning Resource Center, it is the one on the left). 2. Click on the Fundamental of GC-MS icon on the desktop 3. Click on Click Here on the top right corner 4. Click on No Tracking 5. Click on the Table of Contents icon:

6. Click on 1. GC/MS Fundamentals

7. Click on Overview

8. Click on and review the Block Diagram tab, including the Animation. 9. Click on and review the Chromatography tab 10. Click on and review the Mass Spectrometry tab 11. Click on and review the Advantages tab 12. Return to the Table of Contents, 1. GC.MS Fundamentals, and click on Chromatography 13. Click on and review the Equilibria tab 14. Click on and review the GC process tab 15. Click on and review the Retention tab 16. Click on and review the Simulator tab