EXPERIMENT 6: IR / NMR UNKNOWN ANALYSIS

Approach / Guidelines for your Unknown ID

Some General Rules:
a. Internet use is not allowed for looking up structures / NMR spectra. NO
LAPTOPS or iPHONES!!!
b. You may not ask Instructor for help in writing structures or interpreting spectra.
c. You may not collaborate with your peers regarding structures and spectra.
d. You MUST submit all paperwork by the end of the lab period, regardless if you
have finished identification of your known or not. NO EXTRA TIME ALLOWED!
All work must be performed in the lab!
Week 1: IR / NMR Analysis of Solid Unknown
1. Write your unknown # in your lab notebook. This MUST be included in your final
report sheets. Note: you will be given two unknowns a solid and a liquid. You will
perform IR / NMR analysis on the solid this weeks session. The choice will be
determined by the instructor. You will submit the IR Report sheet along with the
corresponding labeled IR spectra. Upon successful identification of the functional
group and listing of the possible compounds that include your unknown, you will
analyze the H-1 and C-13 NMR spectra of your unknown and make the final ID of
it.
2. Take the m.p. Since this is not known, set Mel-Temp to setting for 50 0C. Increase
setting in appropriate (2-3 V) increments every 10 0C rise. Note: The b.p. range for
liquid unknown is provided on the unknown vial label.
3. Take IR of your unknown. For the solid, a specific amount of finely-divided solid is
placed on the diamond window of the solid IR. The sample preparation and
instrument operating procedures have already been demonstrated for the solid IR.
For the liquid , use 1-2 drops between salt plates on the liquid IR (use a capillary
m.p. tube or Pasteur pipette to obtain sample from vial and apply to face of one of
the salt plates). Alternately, you can use the solid IR for the liquid sample.
Results from Steps 4 7 will be entered in the appropriate Preliminary IR Report
Sheet found in your lab manual.

4.. Perform a careful analysis of your IR spectra using Helpful IR Frequencies on

pp. 61-63 in the lab manual. Focus on selecting frequencies for alcohols,
aldehydes, ketones, acids, and phenols. Note the significant absorptions
(wavenumbers) on each of your spectra. IT IS CRITICAL THAT YOUR IR AND
YOUR ANALYSIS OF IT BE GOOD!
5. Along with your IR analysis, note the following specific physical properties: (1)
color (phenols tend to be pinkish or fleshtone, nitro groups or other chromophores
tend to be yellow) ; (2) odor (antiseptic phenols; sour liquid acids ; sweet /
fragrant aldehydes, ketones, esters); and, (3) texture (a sticky / clumpy solid may
be indicative of a low-melting point ).
6. Once you have tentatively identified the functional group present in your
unknown, submit your IR Report Sheet to the instructor. If your ID is correct,
proceed to Step 7. If incorrect, a 10-point deduction will be made and you will need
to re-examine your IR. Return to your instructor with your new functional group
prediction (HOPEFULLY, YOU WILL BE ON THE MONEY!)
7. List names of all compounds with the tentative functional group that are listed in
the tables and are within a specific range (+/- 6 degrees C) of the mid-point of your
solids m.p. range and within the provided boiling point range of your liquid. Also, list
these names in your lab notebook. Note: your unknown may contain more than one
functional group (i.e., phenol and ester / acid).
8. Submit the full Preliminary IR Report sheet AND the properly-labeled IR
spectrum to your instructor. At this point, provided your unknown is on the list of
possible compounds on the Preliminary IR Sheet, the instructor will allow you to
predict the H-1 NMR spectra of all of the possible compounds. You will do all
predictions in your lab notebook. For each compound, include the following:
molecular structure (2D) (look this up in the resources available in the lab);
chemical shift, multiplicity, and integration for each H-1 NMR peak. There will be
special handouts provided that conatin the line structures of all of the possible
unknowns listed in the tables. Use of Internet (ie., laptops / iPhones) is
prohibited, as is networking with your peers!
9. Show the NMR predictions to your instructor. If approved, you will be given the H1 and C-13 NMR spectra of your unknown. Complete the NMR Report Sheet and
submit it along with the properly-labeled H-1 and C-13 spectra- to the instructor.

Week 2: IR / NMR Analysis of Liquid Unknown .

1. Your instructor will return your graded IR and NMR Report Sheets for your solid
unknown to you at the start of lab.
2. Follow the same procedural steps as you did for the solid unknown (except for
the m.p. determination).
3. At the completion of your ID of your liquid unknown, you will perform the checkout procedure as outlined in the course information sheet and additional instructions
from the Stockroom.