CHEM 212 ShowCase 1: Unit 1 Elacqua/Masters 1 Please upload this completed ShowCase 1 on Wednesday, February 24 by 11:59 pm to Canvas. To do so, go to “Assignments” on Canvas and click on the ShowCase 1 assignment. Here, you will be able to upload one pdf file. This ShowCase is worth 94 points. You are allowed to use your class materials and your CHEM 212 textbook. You will need to reference your class notes, ex: Unit 1A Worksheet – topic name, page #. You may work with another student. If so: o Please fill out both students’ info in the table above. o Each team member must upload one file; remember to include both names above. Remember, you can work together via Zoom since each of you have your own Zoom meeting room. Use a Google Jamboard or the Zoom Whiteboard to work out the problems during your virtual meetings. o If you work with a partner on this first ShowCase, you are not obligated to work with that partner again in the future. It’s your choice! o You can work with one other student from either Dr. Elacqua’s section (sec 001) or Dr. Masters’ section (003); do NOT forgot to put both names in the table above! Only use the space provided for your answers! Do not add pages, use the back of the page, etc. Write concisely and neatly! Here are ways to complete and submit this assignment: 1. Print out this case study, hand-draw your answers, scan it*, and upload as a pdf to Canvas. 2. If you do not have a printer, write your answers on blank sheets of paper. Scan and upload as one pdf file to Canvas. 3. Use your tablet to complete it electronically using a stylus. Upload the electronic pdf file to Canvas. *You can use the apps Camscanner or Scannable for scanning documents using your phone. If you have an iPhone, you can use the “Notes” app to generate a pdf file. You must generate one pdf file for submission. It is your responsibility to make sure your submissions are complete and legible. Missing/illegible parts to the assignment will receive no credit and will not be accepted late. Academic Integrity & Honor Code. Please agree to the Honor Code within this Canvas assignment prior to working on this assignment. If you do not agree to the Honor Code, you will earn a zero for this assignment. Student Name(s) & Section 001 or 003 Access ID (e.g. kmm14) CHEM 212 ShowCase 1: Unit 1 Elacqua/Masters 2 FOCUS OF SHOWCASE 1: The Enamorment of Natural Products & Organic Syntheses! Your task is to apply your knowledge to a couple of natural product syntheses….and perhaps daydream about some other potential outcomes as you ponder structures. In this Enamorment ShowCase, you will investigate syntheses as applied to natural products: • To rationalize reaction outcomes • To predict specified reaction outcomes • To validate product formation • To evaluate structures, plus more! As you begin this ShowCase, admire the beauty of these two natural products – cool structures! • Cloven: isolated from clove oil • Longifolene: isolated from pine resins Be prepared to become (even more!) enamored with organic synthesis and our natural world that supplies such lovely compounds! CHEM 212 ShowCase 1: Unit 1 Elacqua/Masters 3 Question 1! GOAL of Question 1: To compare specific aspects of Funk and Johnson’s synthetic routes! 1a. List two similar features shared between compound A (Funk) and compound 1 (Johnson): (2 pts each; 4 pts total) • _____________________________________________________________ • _____________________________________________________________ 1b. List two similar features shared between cloven and longifolene: (2 pts each; 4 pts total) • _____________________________________________________________ • _____________________________________________________________ CHEM 212 ShowCase 1: Unit 1 Elacqua/Masters 4 Question 2: Focus on Funk’s Synthesis! GOAL of Question 2: To dig somewhat deep into Dr. Funk’s synthetic route by investigating two steps (out of the 9 steps) of this route. Be ready to fill in details about this route, discuss naming of compounds, and ponder other potential reactions using the given structures in the route. 2a. Let’s start with compound A and IUPAC naming, fun! • The highest priority family in compound A is the _________________________________. (2 pts) • The parent chain is the (circle one): (2 pts) 6-membered ring / Et • Based on IUPAC rules and the priority naming chart, the correct IUPAC name for compound A is (circle one): (3 pts) 2b. Circle the 2 most electrophilic sites in o 5-ethoxycyclohex-5-enone compound A (on the right here). (2 pts) o 3-ethyoxycyclohex-2-enone 2c. Briefly describe how compound A is o 1-cyclohex-1-enylethane changing into compound B in STEP A: (3 pts) o 1-ethoxycyclohexen-3-one clovene OEt O compound A STEP A reagent A H3O + work-up OEt compound B HO turns out compound B converts to compound B’ under hydronium conditions O we can revisit this reaction when we go over polar acidic reactions! compound B’ Me2CuLi STEP B compound C 7 more steps CHEM 212 ShowCase 1: Unit 1 Elacqua/Masters 5 2d. For STEP A to occur, reagent A is (draw out the specific reagent in the box below): (3 pts) 2e. Show the connection! Reference the reaction in the Unit 1C worksheet that supports your answer. To do so, draw out that example here and give the page number of the worksheet. (4 pts) Now onto STEP B of Funk’s route! 2f. The reagent, Me2CuLi, is a ______________________ (name) reagent. It is considered to be a ( hard / soft ) (electrophile / nucleophile ). For this reason, it will add to the ( carbonyl carbon / alpha carbon / beta carbon ) of compound B’. (4 pts) O compound B’ Me2CuLi STEP B compound C CHEM 212 ShowCase 1: Unit 1 Elacqua/Masters 6 2g. Draw the complete electron-pushing mechanism of STEP B; start with the structure of compound B’ and finish with the structure of compound C. Be sure to include all electron-pushing arrows, intermediates, and formal charges where appropriate. You can assume a hydronium work-up. (6 pts) Please draw compound C in the empty box above (page 5) as well. (3 pts) CHEM 212 ShowCase 1: Unit 1 Elacqua/Masters 7 2h. Hmmm…..compound A is an interesting structure. Let us ponder this question: What if a soft nucleophile reacted with compound A? Consider the given reaction scheme shown here: Your job is to rationalize the formation of compound Z from compound A with the use of a soft nucleophile. • Describe what is o Changing from compound A to compound Z: (2 pts) o Not changing from compound A to compound Z: (2 pts) CHEM 212 ShowCase 1: Unit 1 Elacqua/Masters 8 • 2h (continued) Now, use your CHEM 212 knowledge to: (a) propose a reasonable mechanism that accounts for this transformation. Start with the structure of compound A and finish with the structure of compound Z. Be sure to include all electron-pushing arrows, intermediate structures, and formal charges where applicable. (6 pts) (b) Support your proposed mechanism by giving a reaction and its mechanism from our Unit 1C worksheet that best aligns/has similar features to your proposed mechanism. Please give the page # of Unit 1C worksheet that you are referencing. (6 pts) For your answers to parts (a) and (b), write them out side-by-side to show best this comparison. Proposed mechanism: Compound A to Compound Z Unit 1C Reaction and its mechanism; page # _________ CHEM 212 ShowCase 1: Unit 1 Elacqua/Masters 9 Question 3: Focus on Johnson’s Synthesis! GOAL of Question 3: To dig somewhat deep into Dr. Johnson’s synthetic route by investigating Steps 1-4 of this route. Be ready to fill in details about this route and consider spectral data to distinguish structures. 3a. Draw in the structure of intermediate 1 of STEP 1 in the empty box below. (3 pts) 3b. Draw the complete mechanism of intermediate 1 with the given acid chloride to show how compound 2 is formed. Label the nucleophile and the electrophile as you start your mechanism. Be sure to include all details in your mechanism! (6 pts) O compound 1 7 more steps longifolene STEP 1 CuLi intermediate 1 of this nucleophilic addition step Cl O instead of a hydronium work-up, this intermediate reacts with this given acid chloride to give compound 2! O compound 2 O 2 CH3Li STEP 2 intermediate 2 of this nucleophilic addition step (after 2 CH3Li react) instead of a hydronium work-up, this intermediate reacts with bromine to yield compound 3! Br-Br O compound 3 Br O compound 4 STEP 3 compound 5 LiAlH4 followed by hydronium work-up STEP 4 CHEM 212 ShowCase 1: Unit 1 Elacqua/Masters 10 STEP 2! 3b. Given that CH3Li is a ( neutral / anionic ) nucleophile, this reaction is a polar ( acidic / basic / neutral ) reaction. So, intermediate 2 is ( neutral / anionic / cationic ) and can therefore act as a(n) ( electrophile / nucleophile ). Intermediate 2 reacts with Br2, which must serve as a(n) ( electrophile / nucleophile ). (5 pts) 3c. Draw the structure of intermediate 2 of STEP 2 in the empty box below. (3 pts) 3d. Draw the complete mechanism of the reaction between intermediate 2 and bromine to yield compound 3. Include all details – you know the deal ☺ ! (6 pts) O compound 2 O 2 CH3Li STEP 2 intermediate 2 of this nucleophilic addition step (after 2 CH3Li react) instead of a hydronium work-up, this intermediate reacts with bromine to yield compound 3! Br-Br O compound 3 Br CHEM 210 shout out! CHEM 212 ShowCase 1: Unit 1 Elacqua/Masters 11 3e. STEP 3 is a(n) ( addition / substitution / elimination ) reaction because ______________________________________________________. (3 pts) 3f. STEP 4 uses LiAlH4 to ______________________ the ____________________________ and convert it into a(n) ____________________________ . (3 pts) 3g. Draw the structure of compound 5 in the empty box below. (3 pts) 3h. Fill in the table below to showcase the anticipated diagnostic spectral data differences between compound 4 and compound 5! Spectral Data Type Compound 4 Compound 5 IR spectrum: Give the one signal (~wavenumber value) for each compound that distinguishes them from each other; e.g. N-H, ~3200 cm-1 (2 pts) Proton NMR spectrum: Give one signal (with ppm range) for each compound that distinguishes them from each other; e.g. CHO, 9-10 ppm (2 pts) Carbon-13 NMR spectrum: Give the one carbon signal (with ppm range) in each compound that distinguishes them from each other; e.g. C=C, 100-140 ppm (2 pts) 7 more steps longifolene O compound 3 Br O compound 4 STEP 3 compound 5 LiAlH4 followed by hydronium work-up STEP 4
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