CHEM 136

600 MHz NMR spectrometer in our UCLA facilities (Photo credit: Yves Rubin, All Rights Reserved)

600 MHz NMR spectrometer in our UCLA facilities
(Photo credit: Yves Rubin, All Rights Reserved)

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 5th 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 4th 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)


Personal Protective Equipment

Dangerous chemicals

Safe Handling of Reactive and Explosive Chemicals

List of common carcinogens

Laboratory Techniques:

Thin Layer Chromatography (TLC)

Flash Chromatography


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:



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

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