BRYN MAWR COLLEGE
Organic Chemistry Laboratory
Chemistry 212
Schedule for Semester II, Spring 2017
Bryn Mawr College

 

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Lab Manual
Dates Link to Lab Procedure Description YouTube links Write-up/Due Dates
01/23-01/26

General Lab Information

Laboratory Equipment

The Stereochemistry of Fumarase Mediated D2O addition to Fumarate PDF

See Moodle for Karplus Paper

Set up Fumarase rxn and Yeast Mediated Reduction
Lecture: Fumarase Reaction/Coupling Constant/Stereochemistry

Review of Safety

Worksheet in class and Lab

Prepare your lab book for Fumarase rxn (see link for procedure)by doing the following:
  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)

Realize each lab is a little different. This lab will have a lower emphasis on mechanisms.

Acronym/pneumonic: IMMPDD ( I make molecules productively during daytime)
01/23 to 01/26
(con't)

The Stereoselective Reduction of Ethyl Acetoacetate using Enzymes found in Bakers Yeast pdf

Set up Yeast Mediated Dehyragese Reduction of Ethyl Aceto-Acetoatate

Come back and reincubate during week

 

Prepare your lab book for Yeast Alcohol Dehydrogenes Reduction(see link for procedure)by doing the following:

  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)

Mechanism here does not need to have to include details of enzyme.

 

 

 

 

 

 

 

01/30 to 02/02
(continued)

The Stereochemistry of Fumarase Mediated D2O addition to Fumarate PDF

Run NMR of Fumarase Mediated D2O Addition to Fumarase

Lecture: How Yeast Mediated Reaction Works
NMR of Homofopic enantiotopic and diastereotopic hydrogenes

Prepare your lab book for lab by doing the following (if you are starting new procedure):
  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)
Acronym/pneumonic: IMMPDD ( I make molecules productively during daytime)

Though these components are standard, some weeks in lab you are just recording data, use judgement.

01/30 to 02/02
(continued)

The Stereoselective Reduction of Ethyl Acetoacetate using Enzymes found in Bakers Yeast pdf

Yeast Alcohol Dehydrogenase Mediated Reduction of Ethyl Aceto-Acetate.

Experimental work up to and excluding NMR

Prepare your lab book for lab by doing the following (if you are starting new procedure):
  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)
Acronym/pneumonic: IMMPDD ( I make molecules productively during daytime)

Due Worksheet for Fumarase rxn.
1 (one) per person, in TA's folder by Friday 5 PM.

Though these components are standard, some weeks in lab you are just recording data, use judgement.

 

02/06 to 02/09

The Stereoselective Reduction of Ethyl Acetoacetate using Enzymes found in Bakers Yeast pdf

NMR of Yeast Alcohol Dehydrogenase Mediated Reduction of Ethyl Aceto-Acetate Product

Lecture: More on NMR, Homotopic, Enantiotopic and Diasteriotopc hydrogens and splitting

Prepare your lab book for lab by doing the following (if you are starting new procedure):

  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)
Acronym/pneumonic: IMMPDD ( I make molecules productively during daytime)

This week you do not have total lab set-up, just record data.

 

02/13 to 02/16

Flutamide reaction pdf

Flutamide  Synthesis
Synthesis and Recrystalization

Lecture: Overview Flutamide Chemistry and NMR of Products

Prepare your lab book for lab by doing the following:

  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)
Acronym/pneumonic: IMMPDD ( I make molecules productively during daytime)

This week you have a total lab notebook set-up.

02/20 to 02/24

Flutamide reaction pdf

Recrystallize Flutamide Product
Run IR of Flutamide Product

Run NMR of Flutamide Products. Use time in lab to work on Yeast Alcohol Dehydrogenase Mediated Reduction of Ethyl Aceto-Acetate Product and Flutamide Report - utilize the resources

 

Prepare your lab book for lab by doing the following:

  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)
Acronym/pneumonic: IMMPDD ( I make molecules productively during daytime)

This week you do not have total lab set-up, just record data.

Due Yeast Alcohol Dehydrogenase Mediated Reduction of Ethyl Aceto-Acetate Report, 1 (one) per group in TA's folder by Friday 5 PM.

02/27 to 03/02

Total Synthesis Project pdf

Week One (See Lab Manual)
Read this each week

Lecture: Introduction to and Outline of Total Synthesis Project
Mechanisms of Project

 

Prepare your lab book for lab by doing the following (if you are starting new procedure):

  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)

Acronym/pneumonic: IMMPDD ( I make molecules productively during daytime)

Due Flutamide Synthesis Report at 5 PM in T/A's file.
1 (one) per group.
See Lab Manual and Nerz notes.

Though these components are standard, some weeks in lab you are just recording data, use judgement.

 

03/06 to 03/09

Spring Break

03/14-03/17

Total Synthesis Project pdf

Week Two (See Lab Procedure)
Read Week 3 in Manual.

Lecture: Mechanisms of Project

How to Write an Abstract/Intro to a Paper

You Tube

Prepare your lab book for lab by doing the following (if you are starting new procedure):

  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)
Acronym/pneumonic: IMMPDD ( I make molecules productively during daytime)

See Lab Manual and Nerz notes.

 

03/20 to 03/23

Total Synthesis Project pdf

Week Three (See Lab Procedure)

Lecture: How to write paper I

Abstract intro
Quiz Review *

Note: Wednesday is Community Day at Bryn Mawr.

LAB is Lighter this week.

It is suggested that groups come in on Monday, Wednesday, Thursday or Friday to start synthesis 4-hydroxy Coumaden derivatives.

(talk to your instructor about logistics)
The majoirty of students should focus on QUIZ and writing INTRO draft during lab hours. Please use resources.

Quiz 1 – On first two labs
will be on Moodle on Monday, March 20, 2017

 

Prepare your lab book for lab by doing the following (if you are starting new procedure):

  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)
Responsible for thoroughly looking up procedures thoroughly and prepping notebook as indicated in Lab Manual
See Lab Manual and Nerz notes.

Due Quiz 1 Due by Monday March 27 at 5 PM to Dr. Nerz/Dr. K.

 

03/28 - 03/31

Total Synthesis Project pdf

Week Four (See Lab Procedure)

Lecture: Mechanisms of Total Synthesis
How to Write Paper II Experimential Section

Creativity 101: How to ask a question and design a question.

 

Prepare your lab book for lab by doing the following (if you are starting new procedure):

  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)
Responsible for thoroughly looking up procedure thoroughly and prepping notebook as indicated in Lab Manual
See Lab Manual and Nerz notes.

During lab come up with question and simple experiment.

 

04/03 to 04/06

Total Synthesis Project pdf

Week Five (See Lab Procedure)

Lecture: How to write paper III
References and Discussion
Creativity 101 How to come up with your own question to explore during last weeks of project

 

Prepare your lab book for lab by doing the following (if you are starting new procedure):

  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)

Due Rough Draft of Intro and Abstract(one per group) due to Dr. Nerz/Dr. K by 5 PM Friday.

Responsible for thoroughly looking up procedure thoroughly and prepping notebook as indicated in Lab Manual.

See Lab Manual and Nerz notes.

 

04/10 to 04/13

Total Synthesis Project pdf

Week Six

Lecture: Tying up loose ends on Project Creativity 101/Writing Paper
Exploring your own questions in the lab.

 

Prepare your lab book for lab by doing the following (if you are starting new procedure):

  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)
Due Rough Draft of Experimental Section (one per group) due to Dr. Nerz/Dr. K. by 5 PM Friday


Responsible for thoroughly looking up procedure thoroughly and prepping notebook as indicated in Lab Manual See Lab Manual and Nerz notes.

 

04/17 to 04/20

Total Synthesis Project pdf

Week Seven
Lecture: Quiz review

Quiz 2 on Chemistry and NMR of Total Synthesis Project

 

Prepare your lab book for lab by doing the following (if you are starting new procedure):

  • Intro (statement of purpose, big picture) 10 points
  • Main reaction (10 points)
  • Mechanism (20 points)
  • Procedure from literature with scaling and literature ref. (20 points)
  • Diagrams of apparatus (optional)
  • Data from days lab (20 points)
  • General Preparedness (notebook ready, on-time for lab and clean up) ( 20 points)
Due Rough Draft of Discussion(one per group) due to Dr. Nerz/Dr. K. by 5 PM Friday.

Responsible for thoroughly looking up procedure thoroughly and prepping notebook as indicated in Lab Manual See Lab Manual and Nerz notes.

Due Quiz 2 Due in Dr. Nerz/Dr. K. by 5 PM Friday.

 

04/24 to 04/26

     

Due Total Synthesis Full Paper Due April 28, 2017 5 PM