Lesson two

The 1H NMR activity was presented in the second week of a second-semester, introductory,
undergraduate organic chemistry course. Students were familiar with functional groups, IR( aɪ-ɑr)
spectroscopy, and simple organic reactions and had no exposure( ikˈspōZHər) to NMR
spectroscopy prior(praior) to the activity. The laboratory and lecture course was taught( tɔt) by the
same instructor(instrocchor). The learning activity was completed during two consecutive(kən
ˈsekyətiv) 3-h laboratory periods.

In Week 1, students were introduced(ˌɪntrəˈdust) to 1H NMR spectroscopy terminology including

chemical shift, multiplicity, and integration. Students were not shown specific chemical shift values
but told that electron density impacts signal position. Multiplicity was introduced through proton
equivalency(ɪˈkwɪvələnsi) and the N + 1 rule. Integration was described(dɪˈskraɪbd) as the relative
number of protons that produce a particular signal. A representative NMR spectrum was shown to
illustrate(ˈiləˌstrāt) the three concepts, but peak assignments(əˈsīnmənt) were not done. A
demonstration of sample preparation was performed.

Students were provided(provided) five organic liquids: 2-bromopropane, ethyl acetate, isopropyl
alcohol, MTBE, and p-tolualdehyde. These compounds were selected for their availability(əˌveɪlə
ˈbɪləti), cost, and physical state. Alternative compounds(compaund) can be substituted based on
the discretion of the instructor. Students, self-selected into groups of 2 or 3, were provided two
liquids from the list to prepare NMR samples. Each (ich) group acquired 1H NMR spectra for the
two assigned (əˈsaɪnd) organic liquids and obtained previously acquired data for the other three
liquids. Using guided-inquiry worksheets and the 1H NMR spectra, students prepared chemical
shift graphs (see the Supporting Information).

During Week 2, the groups prepared (priˈpɛrd) an NMR sample of an unknown organic solid, 3,5-
dimethylbenzoic acid. Each group obtained the 1HNMR spectra and interpreted (ɪnˈtɜrprətəd) the
data(daita) to find its plausible structure (strocchor). The instructor provided(provide) a worksheet
that required the students to determine (dəˈtɜrmən) the chemical shifts, integrations, and
multiplicities(multiplicitis) of the signals on the acquired 1H NMR spectra. Guided questions
(kwɛsʧənz) focused (foʊkəst) students on specific areas in the 1H NMR spectra. The students then
were provided five chemical structures and determined the most plausible structure.

In addition, the groups prepared a 3−5 min video using a cell phone or computer describing (dɪ
ˈskraɪbɪŋ) one of the following (fɑloʊɪŋ) topics: chemical shift, integration, and multiplicity. No
more than three groups selected the same topic per laboratory section. Students were instructed
(ɪnˈstrʌktəd) to teach the topic as if they were the instructor.

HAZARDS

Chloroform-d can cause skin and eye irritation and is a suspected (səˈspɛktəd) carcinogen (kɑr
ˈsɪnəʤən). The liquid 2-bromopropane is highly flammable and may cause respiratory irritation.
Ethyl acetate is flammable and can cause eye irritation. Isopropyl alcohol and methyl tert-butyl
ether (MTBE) are highly flammable and can cause eye and respiratory irritation. p-Tolualdehyde is
a combustible liquid and causes eye, skin, and respiratory irritation while 3,5-dimethylbenzoic acid
causes skin, eye, and respiratory irritation. The NMR spectrometer is a magnetic field hazard to
individuals with medical implants. Students should wear appropriate lab attire including gloves,
safety googles, and laboratory coats. Chemicals should be dispensed in a well-ventilated fume
hood. Waste should be disposed of properly.