Chemistry

Final Project SP20 CHEM 40B – Schmidt

DO NOT SUBMIT QUESTION PAGES The Final Project assignment is designed to provide students with a cumulative assignment to demonstrate mastery of CHEM 40B course content. You will be asked to articulate many of the concepts you have learned throughout the course and have the opportunity to explain your thinking. You are encouraged to tailor your responses to highlight your best work. Deadline: June 9, 2020 by 2:30pm PT to Gradescope via Canvas. No late submission will be accepted. All individuals need to submit their own answer sheet, completed and written themselves. Important things to know:

– “Final Project Answer Sheet” should be used to compile all responses to be graded. Please confine answers to be graded to the defined regions. You may download this pdf, mark it with responses using a tablet, save/export as a pdf to submit via Gradescope. If this isn’t available, you may print this pdf, fill it out with responses, scan/photograph and save as a pdf to submit via Gradescope. If this isn’t available, you may create your own answer sheet by writing on a blank sheet of paper and approximating the formatting of the Answer Sheet, fill it out with responses, scan/photograph and save a pdf to submit via Gradescope.

– All generated questions on Answer Sheets should be derived from material covered in CHEM 40B from this SP20 quarter only. Reactions that were covered in previous quarters of CHEM 40B or in other sections offered this quarter, are not permitted. Responses that only make use of CHEM 40A content will receive little credit.

– All chemical structures of organic compounds must be drawn in correct skeletal structure formatting. Point deductions will be applied based on the deviation from this formatting.

To complete this assignment, you MAY:

– Work individually. – Borrow inspiration from online, print, or other resources to produce questions, but your

submitted work should not be plagiarized verbatim. – Consult any lecture notes, course videos, DSW, or course quiz materials. – Consult any textbook, reference textbook, or reference websites. A reference website

would be the online equivalent of books found in the “Reference Section” of a physical library.

To complete this assignment, you MAY NOT:

– Prepare responses through consultation with any person, either in real life or virtually. – Generate questions derived from content not specifically covered in this CHEM 40B class.

Do not incorporate content covered in other CHEM 40B sections offered either concurrently or in the past.

– Use any generic groups in any structure or in the construction of a question (e.g. LG, X, R, etc.).

– Participate in any way, including but not limited to soliciting answers or accessing answers with contract cheating websites, tutors for hire or free, or internet answer banks. Penalty for violation: “F” course grade and subject to further AI sanctions.

– Post Final Project prompts or answers to any publicly accessible website. Penalty of violation: “F” course grade and subject to further AI sanctions.

SP20 CHEM40B DO NOT SUBMIT QUESTION PAGES KDP2 – Schmidt

This is not an exhaustive list. Please do not violate the spirit of these directions or the expectations of academic integrity set forth by this course or UCSD. Failure to adhere to these guidelines is a potentially serious Academic Integrity violation, and those found responsible will be given very severe penalties in accordance with the administrative sanctions provided here: https://academicintegrity.ucsd.edu/process/consequences/sanctioning-guidelines.html. Final Project Prompts [100 points total] 1. Formulate a Ranking-Style Question. [20 points]

a) Please formulate an exam-style question that requires the ranking of the relative reactivities or stabilities of a series of FIVE compounds, intermediates, or structures in a specified reaction, energy levels, etc.

b) Please provide the correct solution to your exam-style question. Your answer should include 5 specific structures without generic groups.

c) Identify the major concept(s) underlying the exam-style question you’ve formulated (1-2 sentences). Explain the reasoning behind the correct answer provided in part b (2 sentences).

2. Design a Mechanism Question. [20 points] a) Design a question (with chemical structures) that requires an arrow-pushing mechanism

that explains the formation of a product from a starting material. The mechanism must progress through at least two distinct intermediates.

b) Please provide the correct, full arrow-pushing mechanism answer to your designed question. Be sure to include all formal charges where appropriate.

c) Identify the major concept(s) underlying the mechanism question you’ve formulated (1-2 sentences). Explain the reasoning behind the correct answer provided in part b (2 sentences).

3. Compose a Missing Starting Material Question. [20 points]

a) Please compose an exam-style question that asks to provide a missing starting material. This may not duplicate material from Question 4 below or draw from the same Chapter (note that Chapters 15 and 16 are considered as one).

b) Please provide the correct missing starting material and label which chapter the question is derived from.

c) Identify the major concept(s) underlying the question you’ve formulated (1-2 sentences). Explain the reasoning behind the correct answer provided in part b (2 sentences).

4. Compose a Missing Product Question. [20 points]

a) Please compose an exam-style question that ask to provide a missing product. This may not duplicate material from Question 3 above or draw from the same Chapter (note that Chapters 15 and 16 are considered as one).

b) Please provide the correct answer missing product and label which chapter the question is derived from.

c) Identify the major concept(s) underlying the question you’ve formulated (1-2 sentences). Explain the reasoning behind the correct answer provided in part b (2 sentences).

SP20 CHEM40B DO NOT SUBMIT QUESTION PAGES KDP2 – Schmidt

5. Propose a Synthesis. [20 points] a) Stepwise synthetic sequences provide a design plan for converting a given starting

material into a specific product that cannot be accomplished in a single chemical reaction. Three separate options are provided below with starting materials and targeted products. Please select ONE option and propose a synthetic sequence requiring no more than 4 total synthetic steps. Be sure to provide all starting materials, reagents, reaction conditions (as needed), and products from each synthetic step (mechanisms should not be provided).

b) Explain the reasoning behind the given answer (2 sentences).

Synthesis Option A

O4 synthetic steps or less

Synthesis Option B

4 synthetic steps or less OH

O

Synthesis Option C

4 synthetic steps or less O

H

H

H

H O

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