Organic Spectroscopic Methods

Material covered along the timeline of this course:

• Introduction, Purification, Lab Techniques
• Infrared Spectroscopy, Example Problems
• Introduction to 1D NMR
• NMR Coupling Constants and Advanced Techniques
• Carbon-13 NMR
• 2-Dimensional NMR
• Mass Spectrometry
• X-ray Crystal Structure Analysis

Course Structure:

Syllabus Chem 136 Spring 2016

Teaching Assistants:

• TA list (see syllabus)

For questions please e-mail me at my Gmail teaching account: Prof. Yves Rubin

Problems Sets (Pavia-Lampman-Kriz-Vyvyan 5^th Ed):

Problem Set 1:	2.1, 2.3, 2.4, 2.5, 2.8, 2.9, 2.10 (IR)	Due April 7
Problem Set 2:	5.17, 5.19, 5.20, 5.21, 5.22, 5.23 (simple 1H NMR)	Due April 14
Problem Set 3:	7.3, 7.4, 7.9, 7.10, 7.13, 7.14 (1H NMR)	Due April 21
Problem Set 4:	7.16, 7.17, 7.18, 7.22, 7.22, 7.26 (1H NMR)	Due April 28
Problem Set 5:	6.3, 6.4, 6.5, 6.9, 6.10, 6.11, 6.15 (13C NMR)	Due May 12
Problem Set 6:	8.2, 8.3, 8.8, 8.9, 8.10, 8.11, 8.15, 8.19 (1H NMR)	Due May 19
Problem Set 7:	11.2, 11.9, 11.10, 11.14, 11.31 (combined problems)	Due May 26
Problem Set 8:	9.2, 9.3, 9.4, 9.7, 9.8   (2D NMR)	Due June 3 (TA)

Note: the problems from Pavia-Lampman-Kriz-Vyvyan 4^th Ed have been reorganized to some extent, so please do not use this edition unless you can compare the order with a classmate’s 5th edition.

Practice Exams:

Midterm_Exam (2012)

Midterm Exam answer key (2012)

Final Exam (2011)

Final Exam answer key (2011)

Handouts

Safety:

Personal Protective Equipment

Dangerous chemicals

Safe Handling of Reactive and Explosive Chemicals

List of common carcinogens

Laboratory Techniques:

Thin Layer Chromatography (TLC)

Flash Chromatography

Recrystallization

Vacuum Distillation

IR spectra:

IR Spectra Handout for class presentation

IR-ATR Instrument Instructions

1D NMR Spectra:

Great YouTube videos explaining the principles of NMR spectroscopy (watch especially videos 1-4)

Coupling constants for 1H and 13C NMR

2D NMR Spectra:

Geraniol 2D INADEQUATE spectrum

2D NMR Technical Instructions for Running Experiments:

2D COSY

2D NOESY

HMQC (1-bond H-C correlations)

HMBC (2 or 3-bonds HC correlations)

other Molecular Instrumentation Center (MIC) handouts

Lab Handouts and Report Forms

Experiment 1:

Guided procedure for UNKNOWN 1
 (this handout is also your report form for this experiment)

Tables of melting points for derivatives of ketones or amines

Experiments 2-5 (Report form for Unknowns):

Unknown_Report_Sheet_2014 (PDF)

Unknown_Report_Sheet_2014 (Word)

Example of Chem 136 Lab Report (for 2nd to 5th unknowns, but done using older format)

Experiment 4:

Piperine extraction from black pepper

Isolation of Curcumin from Turmeric

Experiment 5:

Rheosmin “Raspberry Ketone”

Strawberry Flavoring Agent

Other useful library sources:

High Resolution NMR Techniques in Organic Chemistry by T.D.W. Claridge; Pergamon, 2nd Edition, 2009

Structure Elucidation by NMR in Organic Chemistry by Breitmaier; Wiley, 3rd Edition, 2002

Spectroscopic Methods in Organic Chemistry by Hesse, Meier, Zeeh; Thieme, 2nd Edition, 2008

Vogel’s Textbook of Practical Organic Chemistry by Vogel; Prentice Hall, 5th Edition, 1996