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Old Dominion University *

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Chemistry

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Feb 20, 2024

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Epoxidation of Citral Chem 30BL Name: ___________________________________________ Section: ___________________ Pre-Lab Assignment (17 points) 1. (1 point) Describe a key role that chemists can play in the fragrance industry. 2. (1 points) Citral is a naturally occurring molecule, also known as a ‘natural product’. Other natural products or structural derivatives have been used as fragrances. Using online search engines, identify one other molecule. Provide the name, structure, and where the plant was isolated from. Chemists can take naturally occurring compounds and perform chemical reactions to create new scents . Linalool Ho Err Linalool is extracted from the lauendar Plant
Epoxidation of Citral Chem 30BL Name: ___________________________________________ Section: ___________________ 3. (1 point) Describe a safety concerns you have about performing this particular experiment specifically in regards to hydrogen peroxide. 4. (4 points) Draw the arrow-pushing mechanism for the epoxidation of citral being performed in this laboratory experiment and state the role of NaOH. Mechanism: role of NaOH: Hydrogen peroxide can be corrosive to the eyes , skin , and lungs . Thus , I want to be careful not to innate hydrogen peroxide , get it on my skin or in my eye . If I have the proper PPE on [ gloves , safety goggles , mask ) it should not be a problem . H - o - F- H OOH H - o - o_0 innit " t im ¥ i aÉÉ : H deprotonate Hzoz
Epoxidation of Citral Chem 30BL Name: ___________________________________________ Section: ___________________ 5. (2 points) Explain why ‘Alkene A’ does not react with H 2 O 2 and NaOH but ‘Alkene B’ does. Use resonance structures to support your answer if applicable. 6. (2 points) Do you think the Rf value for the starting alkene will be higher or lower compared to the epoxide product? Explain your rationale. O Alkene A Alkene B Alkene A is electron rich while Alkene B is election deficient due to the carbonyl group - ° c- o_0 - electron deficient since the epoxide makes the molecule slightly more polar due to the c- 0 bond , the Rf value for the starting alkene will be higher compared to the epoxide product .
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Epoxidation of Citral Chem 30BL Name: ___________________________________________ Section: ___________________ 7. (2 points) You will be doing an aqueous workup with diethyl ether as the organic solvent. Identify each layer of the extraction (‘organic’ or ‘aqueous’). Which layer do you expect will be on the bottom? Use the densities of water and diethyl ether to figure this out. 8. (4 points) How many alkene C-H peaks would you expect to see in the 1 H NMR spectrum of the citral starting material? What about when it is converted into the epoxide product? Please list the number of alkene C-H peaks, the integration, and the splitting pattern. # of C-H alkene peaks, integration, splitting pattern Alkene starting material: # of C-H alkene peaks, integration, splitting pattern Epoxide product: O Me Me Me O Me Me Me O ( organic ) diethyl ether 0713 51mL diethyl ether water o - 998 91mL water C aqueous > Ha 1 I 1 His Hc 3 c- H alkene peaks Ha int - =\ splitting = doublet pattern 1-19 Hb int =/ splitting = doublet 1 pattern 1 He in -1=1 splitting = triplet pattern Hb 2 C - H alkene peaks Ha int =/ splitting = doublet pattern Hb int =/ splitting pattern = triplet