Chemistry 211, Schedule for Semester I, Fall 2015

Organic Chemistry Laboratory
Chemistry 211
Schedule for Semester I, Fall 2019

Bryn Mawr College

Chem 212 General

Useful Web Sites

Lab Manual
Dates	Link to Lab Procedure	Description	YouTube links	Write-up
9/02-9/05	No lab meeting this week, start reading these documents General Lab Information (pdf) Forces and Factors (pdf) Laboratory Equipment (pdf)	Readings on Organic Lab in General and some basic theory. Lab Lecture: Orientation SAFETY Distillaiton Basics	General safety: Chemical exposure: Fire safety: Thermal Cuts and Burns: How to Build a Proper Still: part I How to Build a Proper Still: part II How to Run a Basic GC	Nothing due. Set up lab book, table of contents, obtain goggles, notebook. Work on reading. Acronym/pneumonic: IMMPDD ( I make molecules productively during daytime)
09/09 - 09/12	Print and read these documents General Lab Information Fractional Distillation, Steam Distillation, Simple Distillation and Gas Chromatography (pdf) Week One: Gas Chromatography/Steam Distillation Check-in	General Readings on Organic Lab. Distillation and Gas Chromatography, Procedure for Lab. Lab Lecture: Distillation/Gas Chromatography	General safety: Chemical exposure: Fire safety: Thermal Cuts and Burns: How to Build a Proper Still: part I How to Build a Proper Still: part II How to Run a Basic GC	Prepare your lab book for Steam Distillation and Gas Chromatography. Prepare your lab book for lab by doing the following: Intro (statement of purpose, big picture) 10 points Main reaction (10 points) for synthetic labs only Mechanism (20 points) for synthetic labs only 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)
9/16 - 9/19	Print and read these documents. Fractional Distillation, Steam Distillation, Simple Distillation and Gas Chromatography (pdf)	Readings on Organic Lab in general. Distillation and Gas Chromatography, Procedure for Lab. Lab Lecture: Recrystallation/Melting Point	General safety: Chemical exposure: Fire safety: Thermal Cuts and Burns: How to Build a Proper Still: part I How to Build a Proper Still: part II How to Run a Basic GC	Prelab for Distillation of lab due. Set up lab manual. Prepare your lab book for lab by doing the following: Intro (statement of purpose, big picture) 10 points Main reaction (10 points) for synthetic labs only Mechanism (20 points) for synthetic labs only 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)
9/23-9/26	Print and read these documents. Recrystallization and Melting Point Determination: Yield vs. Purity (pdf)	Readings on Recrystallation and Melting Point Lab procedure. Lab Lecture: Extraction	Recrystallization Melting point depression and broadening How to pack a melting point capillary and measure a melting point	Write up for Distillation lab due. Prelab for Recrystallization. Prepare your lab book for lab by doing the following: Intro (statement of purpose, big picture) 10 points Main reaction (10 points) for synthetic labs only Mechanism (20 points) for synthetic labs only 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)
09/30-10/03	Print and read these documents. Extraction of Caffeine from Tea (PDF)	Extraction of caffine from tea. Rotary evaporation Sublimation Lab Lecture: IR Spectroscopy NMR Workshop in Lab	YouTube on separation of acids and bases How to Flute Filter Paper Rotary Evaporation: part I Rotary Evaporation: part II Sublimation Some Instruction on how to do the arrow formalism Soxhlet extraction	Prelab extraction due. Postlab for recrystalization due. Prepare your lab book for lab by doing the following: Intro (statement of purpose, big picture) 10 points Main reaction (10 points) for synthetic labs only Mechanism (20 points) for synthetic labs only 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)
10/07 - 10/10	Week 1 of Spectroscopy Workshop Print and read these documents. Introduction to Spectroscopy	Determination of the Identity of an Unknown Organic Liquid using IR, NMR, Physical and Chemical properties. Obtain IR of unknown during workshop break Lab Lecture: NMR Theory Work on NMR spectra during lab workshop	Making up samples for IR and running new FTIRS IR landscapes How to prepare sample for NMR How to Inject a Sample into the NMR at Bryn Mawr College How to Run NMR Sample at Bryn Mawr College part I How to Run NMR Sample at Bryn Mawr College part II How to Run NMR Sample at Bryn Mawr College part III How to solve a basic NMR Problem A practice NMR problem A practice NMR problem Solution to basic NMR problem no. 3 Solution to NMR Problem no. 4 NMR Theory NMR Theory of Chemical Shift Spectroscopy as Imagery How to make a GCMS sample General Orientation to Gas Chromatograph Mass Spectrometer Mass Spectrometer	Postlab to Caffine Extraction Lab due. Prepare your lab book for lab by doing the following: Intro (statement of purpose, big picture) 10 points Main reaction (10 points) for synthetic labs only Mechanism (20 points) for synthetic labs only 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)
10/14-10/18	Fall Break
10/22 - 10/25	General: Week 2 of Spectroscopy Workshop (continued ...) Introduction to Spectroscopy	Determination of the Identity of an Unknown Organic Liquid using IR, NMR, Physical and Chemical properties. Obtain IR of unknown during workshop break Obtain GCMS for unknown Run NMR of unknown Carry out boiling point, solubility tests etc. Lab Lecture: Introductory GCMS Molecular Weight, Some Simple Fragmentation	Making up samples for IR and running new FTIRS IR landscapes How to prepare sample for NMR How to solve a basic NMR Problem A practice NMR problem A practice NMR problem Solution to basic NMR problem no. 3 Solution to NMR Problem no. 4 NMR Theory NMR Theory of Chemical Shift Spectroscopy as Imagery How to make a GCMS sample General Orientation to Gas Chromatograph Mass Spectrometer Mass Spectrometer	Postlab to Caffine Extraction Lab due. Prepare your lab book for lab by doing the following: Intro (statement of purpose, big picture) 10 points Main reaction (10 points) for synthetic labs only Mechanism (20 points) for synthetic labs only 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)
10/28 - 10/31	General: Week 3 of Spectroscopy Workshop Introduction to Spectroscopy	Work on assigned NMR problems. Work on lab report for this lab. Lab Lecture: Carbocaton Rearrangement as related to synthesis of the Terpene Limonine Intro to GCMS Identification	Making up samples for IR and running new FTIRS IR landscapes How to prepare sample for NMR How to solve a basic NMR Problem A practice NMR problem A practice NMR problem Solution to basic NMR problem no. 3 Solution to NMR Problem no. 4 NMR Theory NMR Theory of Chemical Shift Spectroscopy as Imagery How to make a GCMS sample General Orientation to Gas Chromatograph Mass Spectrometer Mass Spectrometer	Prepare your lab book for lab by doing the following: Intro (statement of purpose, big picture) 10 points Main reaction (10 points) for synthetic labs only Mechanism (20 points) for synthetic labs only 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)
11/04-11/07	Synthesis of the Terpene Limonene Limonene Lab Safety Practice GCMS	Lab Lecture: S_N2/Chromatography Theory of S_N2 Reaction Intro to Thin Layer Chromatography (TLC) Lab Quiz 1: at discrection of instructor.	CGMS Intro CGMS - Prep of Sample	NMR Lab Report Due, one per group. Lab Quiz 1 - Spectroscopy (IR and NMR) closed book - obtain in library. Must be completed by 11/02. Prepare your lab book for lab by doing the following: Intro (statement of purpose, big picture) 10 points Main reaction (10 points) for synthetic labs only Mechanism (20 points) for synthetic labs only 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)
11/11 to 11/14	S_N2 rxn Week 1 Safety Notes for S_N2 rxn	Carry out S_N2 Preparation of Alkyl Umbifellifrones Lab Lecture:More on TLC Review Spectroscopy	Basics of TLC (PDF)	Terpenc lab report due, one per person. Prepare your lab book for lab by doing the following: Intro (statement of purpose, big picture) 10 points Main reaction (10 points) for synthetic labs only Mechanism (20 points) for synthetic labs only 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)
11/26-11/29	No Lab - Thanksgiving
11/25 - 11/28	S_N2 rxn Week II Safety Notes for S_N2 rxn	S_N2 Reaction/Thin Layer Chromatography Purification Characterization Lab Lecture: Redox		Prepare your lab book for lab by doing the following: Intro (statement of purpose, big picture) 10 points Main reaction (10 points) for synthetic labs only Mechanism (20 points) for synthetic labs only 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)
12/02 - 12/05	Oxidation of Isoborneol with bleach Oxidation of Isoborneol to Camphor	Carry out Redox Reaction Purify Lab Lecture Review for Quiz		SN₂ Lab report due - one per person Prepare your lab book for lab by doing the following: Intro (statement of purpose, big picture) 10 points Main reaction (10 points) for synthetic labs only Mechanism (20 points) for synthetic labs only 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)
	Check out. No lab due. Lab Quiz 2 second half of course. (At instructor's discretion)	Check out Lab Quiz 2 - Spectroscopy Including Mass Spec.		Worksheet for Oxidation Due - one per person Lab Quiz available must be completed by end of week.