CHEM 343 - Spring 2020

Advanced Topics in Modern Chemistry
Green Chemistry: Theory and Practice

Instructor:
Professor (adjunct) Irv Levy
Director, Green Chemistry Commitment
Associate Editor, Green Chemistry Letters and Reviews
email: irv.levy@simmons.edu
office: S-421
phone: 617-521-3876

Description:

Chemistry is unique among the sciences because of its focus on transformation of matter from one material into another. To be sure, there are more discoveries in chemistry than in any other scientific discipline because each day of the week a productive chemist could synthesize molecules that have never been known to previously exist. This fundamental manipulation of matter at the molecular level gives rise to enormous power. As with any powerful set of tools, there are also significant hazards that one might encounter if working carelessly. To that end, the toolbox of chemical transformations that have been used throughout the past century is slowly becoming populated with alternatives that are designed to be inherently safer for human health and the environment.

In addition to learning about green chemistry you will move from Theory to Practice as you experience a number of curated laboratory experiences and then you will move to the next step, developing novel green chemistry laboratory experiences for others to use as part of a team project near the end of the semester.

It is hoped that students in this course will become advocates for green chemistry, helping to advance the field into this century in pathways designed to be safer for human health and the environment.

Required text and materials:

Safety goggles

Lab coat

Bound composition book for lab notebook

Green Chemistry: Theory & Practice, Anastas & Warner, 1999

Evaluation:

Students are expected to attend and be actively involved in each class session and the discussions that are held. Passive attendance is not an acceptable substitute. Come with opinions and questions and be ready and willing to share them.

On several occasions you will be asked to lead the discussion of the topic for the day. On these days you need to come prepared with discussion prompts and you need to elicit conversation from the others in the class. You are not expected (or even encouraged) to turn this into a formal PowerPoint presentation. This is simply informal discussion-based leadership. After the session, you will receive feedback on your leadership for the day with recommendations for improvements, as needed.

A take home examination will be assigned about halfway through the course. This will cover the technical concepts discussed in the course and will be open book, note and web. Students are encouraged to take good notes throughout the course when reading (especially important) and participating in discussion.

A major component of this course is the lab work that we will perform. Students must come prepared for every lab, as described below, and will be expected to document their work in a laboratory notebook. The quality of the notebook will be assessed by an oral exam administered to each student during the final week of the course. One week after any preparation is completed, a lab précis is to be submitted. This will typically be not more than one page, word processed, and will provide key results (yield and other metrics) and a brief description of the green principle(s) embodied in the activity, as well as a critique. The report is evaluated in terms of timeliness, completeness and language usage; however, the success of the lab activity is not considered in the evaluation. Reports must be submitted on the date for which they are assigned or they will receive a significant late penalty. Under no circumstance will any report be accepted more than one week late.

Near the end of the course, students will work in teams to develop a new green chemistry lab experience for use in high school or undergraduate college general chemistry, organic chemistry or analytical chemistry. This project will require a lot of independent work and good communication among partners and the professor. The successful project will be ready to be deployed in the curriculum at the end of the course and students will be encouraged to “market” the method to an instructor who might wish to use this in her or his teaching.

Each team will prepare a 30-minute PowerPoint presentation for their project to be shared during the final exam period as scheduled by the Registrar. Ideally, the audience of this presentation will include the instructor(s) to whom these methods are being marketed. The project will be both self-evaluated and evaluated by the professor.

Weighted Scores:

5- Active attendance (15 sessions)

20- Class leadership and occasional writing assignments (equally weighted)

25- Midterm

5- Lab preparation

10-Lab précis

10-notebook and oral exam

25- Project presentation (during finals week; self and professor evaluation)

Grades will be assigned according to

A [93-100] A- [89-93)

B+[87-89) B [83-87) B- [79-83)

C+[77-79) C [73-77) C- [69-73)

D [59-69)

No pass: 59 or lower

Disabilities:

Reasonable accommodations will be provided for students with documented physical, sensory, systemic, cognitive, learning, and psychiatric disabilities.  If you have a disability and anticipate that you will need a reasonable accommodation in this class, it is important that you contact the Director of Disability Services early in the semester. Students with disabilities receiving accommodations are also encouraged to contact their instructors within the first 2 weeks of the semester to discuss their individual needs for accommodations.

Religious Observance and Athletics:

Accommodations for religious observance and athletic competitions will be given, provided at least a one-week advance notice is given to the instructor. If a one-week advance notice is not given, the student is responsible for all graded materials, including exams, quizzes, homework assignments and laboratories.

Lab Preparation:

It is absolutely essential that all pre-lab work be completed as assigned below. At each lab session you must be equipped with:

_ safety goggles & lab notebook (bound composition book)

_ list of all substances to be used in the lab with details:

_ name

_ structure

_ formula weight

_ if solid: melting point

_ if liquid: boiling point and density

_ GHS icons, signal word, and hazard phrases

_ balanced reactions for all transformations

_ computations: limiting reagent, theoretical yield, atom economy, estimate of e-factor

_ special preparation as directed

_ step-by-step procedure
After the lab is complete you will need to:

_ measure melting point (in triplicate)

_ record IR spectrum

_ Record NMR spectrum on products as directed

_ compute percent yield

_ compute process mass intensity (PMI)

_ For all calculations, you must show your work in the notebook (this applies to atom economy, e-factor estimate, % yield and PMI). Numbers without expressions will not be acceptable. In all numeric work, you must observe proper use of significant digits.

For the step-by-step procedure requirement, you will take the sentences in the lab method and convert them into individual operations that you can actually perform in one step. For example, consider this sentence from some procedure:

"Dissolve 5.0 millimoles of benzophenone in 10 mL acetone in a standard test tube and slowly add 4.0 millimoles benzaldehyde while continuously stirring in an ice bath".

For your step-by-step procedure, you have to make everything "do-able". For example, you need to change millimoles to mass (for a solid) or volume (for a liquid) and also consider all of the other requirements. So the step-by-step procedure for this one sentence might become

1. [ ] Set up ice bath

2. [ ] Get stirring plate

3. [ ] Obtain 0.91 g benzophenone

4. [ ] Add benzophenone to a standard test tube

5. [ ] Obtain 10 mL acetone

6. [ ] Add the acetone to the test tube

7. [ ] Put a small stir bar in the test tube

8. [ ] Clamp the test tube into ice bath over stir plate

9. [ ] Turn the stirrer on

10. [ ] Stir tube until solid dissolves, then keep stirring

11. [ ] Use a micropipette to transfer 408 µL benzaldehyde to small test tube

12. [ ] Add a drop of benzaldehyde every 15-30 seconds (ASK)

Note the use of little checkboxes that you can use to keep track of exactly where you are in your procedure. Note that I changed the millimoles to grams for the solid and to microliters for the liquid. I also had to decide what the procedure meant by "add slowly". Because it was a vague instruction, that's probably something you would need to ask about in the pre-lab discussion.

Arrival at class without these materials will result in a delay in your ability to begin working since no one will be allowed to work in the lab without all of the above. After a one-time grace period, any student arriving at lab without one or more of the requirements above will be counted as absent from the lab even though they may be allowed to work after completing the necessary preparations.

TENTATIVE SCHEDULE

1/17

Introduction and Syllabus

What is green chemistry?

Background – why am I teaching this?

What is green chemistry not?

Why is this needed?

Accidents happen!

USCG National Response Center

HOMEWORK

Reading – GC:T&P- Chapters 1-3

View Video:

The Green Chemistry Genesis Story - JOHN WARNER VIDEO

- 2014 Bioneers ( if your birthdate is January - June)

- 2018 Bioneers (if your birthdate is July- December)

Writing assignment and discussion prompt (choose one)

A. Using the video you watch as a prompt write a letter to one of your former chemistry teachers (K-16) encouraging her / him to consider green chemistry as a topic for her / his course in the future. Maximum 1 page, word-processed.

B. Compare and contrast green chemistry and environmental chemistry. Maximum 1 page, word-processed.

Prepare to lead SDG discussion

Lab prep for next week

1/24

Chapter 1- Introduction

Chapter 2 – What is green chemistry?

Chapter 3 – Tools of green chemistry

Discussion led by student

UN SDGs 1-17; how can GC help to address each of these, if at all?

Discussion led by all students

E-factor, PMI, atom economy, etc.

Preparation of benzaldehyde (Assor & Levy)

_ Search the organic chemistry textbook to see the method typically presented for oxidation of 1° alcohols to aldehydes; Why is the presented method greener?

1/31

Chapter 4 – Principles of green chemistry 4.1-4.6

Discussion led by student

Greener aromatic nitration (Nauman & Levy)

2/7

Chapter 4 – Principles of green chemistry 4.7-4.12

Discussion led by student

Thiamine-catalyzed synthesis of a quinoxaline (Levy)

Mechanochemical solvent-free synthesis of nitrofurantoin (WHO Essential Medicines list) (TBA)

View DOZN webinar (to be posted)

Register to use the DOZN tool

2/14

Chapter 5 – Evaluating the effects of chemistry

Discussion led by student

Green Screen Lite presentation

Ecotoxicity experiment (Levy)

Enzyme-catalyzed synthesis of divanillin (J Chem Educ modified)

2/21

Chapter 6 – Evaluating feedstocks and starting materials

Discussion led by student

Aqueous Diels-Alder reaction (Tischler, to be emailed to class)

DOZN - Greener Alternatives Evaluation Matrix

2/28

Chapter 7- Evaluating reaction types

Discussion led by student

Benzylic bromincation – week 1 (J. Chem. Educ.) - TBA

Read J. Chem. Educ. 2019, 96, 7, 1389-1394 for background only.

3/6

Chapter 8 – Evaluation of methods to design safer chemicals

Discussion led by student

benzylic bromination – week 2

Prep for Green Chemistry: Letters & Reviews papers

3/13 SPRING BREAK

3/20

ACS meeting is happening…

1. Midterm distributed by email
2. 6:00 PM ZOOM MEETING FOR GC:L&R PAPERS

Irv Levy is inviting you to a scheduled Zoom meeting.

Topic: CHEM343 class meetup

Time: Mar 20, 2020 06:30 PM Eastern Time (US and Canada)

Join Zoom Meeting

https://zoom.us/j/887460495?pwd=TzBZNmVtMjd5aitRSHBYb3IyalcyZz09

Meeting ID: 887 460 495

Password: 999265

One tap mobile

+19292056099,,887460495# US (New York)

+16699006833,,887460495# US (San Jose)

Dial by your location

+1 929 205 6099 US (New York)

+1 669 900 6833 US (San Jose)

Meeting ID: 887 460 495

Find your local number: https://zoom.us/u/aeGjqHGo4l

3/27

Midterm collected.

Chapter 9 – Examples of green chemistry

Discussion led by student

TBA

4/3

Chapter 10 – Future trends in green chemistry

Discussion led by student

4/10,17,24,5/1

Begin PROJECTS

Examples of topics, others suggested by students are also welcome:

Other nitrations; acetanilide

Alternate Diels-Alder

Greener Bromination

Olefin Metathesis

Green Direct Amidation

Iron-mediated reduction of nitro to amine

Multicomponent reactions

Iron-catalyzed aromatic coupling

----------------

When scheduled by the Registrar

Final exam – Project presentations