BRYN MAWR COLLEGE
Organic Chemistry Laboratory
Chemistry 211
Schedule for Semester I, Fall 2018
Bryn Mawr College

 

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Lab Manual

Dates Link to Lab Procedure Description YouTube links Write-up
9/03-9/06

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

Nothing due. Set up lab book, table of contents, obtain goggles, notebook. Work on reading.

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

09/10 - 09/13 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

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)
9/17 - 9/20 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

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)
9/24-9/27 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

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)
10/01-10/04 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

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)
10/08 - 10/11

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
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)
10/15-10/28

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

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)
10/29 - 11/01

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

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)
11/05-11/08

Synthesis of the Terpene Limonene

Limonene Lab Safety

Practice GCMS

Lab Lecture: SN2/Chromatography

Theory of SN2 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)
11/12 to 11/15 SN2 rxn Week 1

Safety Notes for SN2 rxn
Carry out SN2

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

11/26 - 11/29 SN2 rxn   Week II

Safety Notes for SN2 rxn

SN2 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)
12/03 - 12/06

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.