EFT-NMR in the Undergraduate Laboratory

Spectra of Organic Lab Products

Grignard Reaction Worksheet
Grignard reaction
experiment references.
triphenylmethanol spectra
60 MHz I H spectrum
15 MHz 13C DEPT135 spectrum
15 MHz 13Cspectrum
~MgBr
0 +
cfo
-P'
I I
~ ~
.
Kenneth L. Williamson Macroscale and Microscale Organic Experiments. 2nd edition, 1994,
Houghton Mimin Co.
Dana W. Mayo, Ronald M. Pi!te, and Samuel S. Butcher. Microscale Organic Laboratory. 2nd
edition, 1989, John Wiley &Sons
Oscar R Rodig, Charles E. Bell. Jr., and Allen K. Clark. Organic Chemical Laboratory:
Standard and Microscale Experiments, 1990, Saunders College Publishing
.
15.00
--.J1.o 1
I I I I I I I I I I I I I I I I 1 I I I I I I I I I I I I I I I I I I I I I I I
8 7 6 5 4 3 2 ppt.,
~""""""'I!\L~?~~11if/I
~
E
!1
~
~
~
!Ii:
~
2)
i::
I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I
150 140 130 120 110 100 90 80 70 ppt.,
sample preparation 110 mg (0.43 millimole) of triphenylmethanol (Eastman) was dissolved inCDC13
I.ether
y
-----.
0-6OH
+
MgBr(OH:
2. H30+
triphenylmethanol
Grignard reaction
~MgBr
0
+
c~
experiment references.
.
Kenneth L. Williamson Macroscale and Microscale Organic Experiments. 2nd
edition, 1994, Houghton Mifflin Co.
Dana W. Mayo. Ronald M. Pike. and Samuel S. Butcher, Microscale Organic
Laboratory, 2nd edition. 1989. John Wiley &Sons
Oscar R. Rodig. Charles E. Bell. Jr.. and Allen K. Clark. Organic Chemical
Laboratory: Standard and Microscale Experiments, 1990, Saunders College
Publishing
benzoic acid spectra
~07
.00
60 MHz 1H spectrum
I I . I I I I I , I . , , , I I . . . I I I I I I . I , . I' . . , I ' , , I I' . . . I' , , .
13 12 11 10 9 8 7 6 5 PPr-,
15 MHz 13C DEPT135 spectrum
, L ,4~'''''_- ..
11
~
Ii;
~
~
15 MHz 13Cspectrum
-1 r . ., .....
- ~
T
200
T
120
T
100
1
PPr-,
sample preparation 200 mg, (1.3 millimole) of benzoic acid (Aldrich) was dissolved in DMSO-d..
data acquisition parameters 'H spectra:
I3C DEPT 135:
RG=3
NS=16
data processing 'H spectra:
I3C spectra:
Integral regions were chosen in the ID sub-routine
Spectra were phased using the PE routine
total spectrometer time 'H spectrum:
I3C spectrum:
I3C DEPT 135:
< 5 minutes
< 10 minutes
< 6 minutes
I.ether
aCOOH
.
I +
2. H30+
MgBr(OH)
benzoicacid
i!!
L
I
. , ,
I
' , I
I
180 160 140
About the Worksheet Series...
Goals
The purpose of Anasazi Instruments, Inc. Worksheet Series is to provide information about how the Aii EFT-NMRmight be used
by undergraduates in teaching labs to characterize their products, followreaction kinetics and investigate molecular structure.
If there are specific applications in your field of chemistry which you'd like to see discussed in the Worksheet Series, please
contact Aii with the detailsl
Worksheet Conventions
SlJectra:
The spectra shown in this Worksheet were acquired for compounds in 5mm NMRtubes using the Aii EFT-60 spectromete"r
equipped with an Anasazi Instruments, Inc. 'HI"C NMRprobe. The sequence of data acquisition was 'H data followed
immediately by 13Cdata acquisition. EFT-60 spectrometer operation is automatically switched from 'H to I3Cor vice versa by
typing NU Hl or NU Cl3 at the software data acquisition prompt.
Samnle Concentration:
All I3CNMRspectra were acquired with signal averaging. Where solubility allowed, the amount of compound was selected such
that a useable I3Csurvey spectrum could be obtained by averaging a total of 64 acquisitions (6 minutes.)
Data ACQuisitionParameters
Spectra were acquired and processed using the EFT-60 library of automated NMRdata acquisition sequences and NMRdata
processing MACROS. The standard parameters for the NMRexperiments are listed below. Any changes to these parameters are
indicated in the body of the Worksheet.
SI
NS
DS
RG
PW
RD
SW
SF
DF
Total Acquisition Time
'H survey I3C survey
13CDEPT
8192 16384 16384
1 64 32
004
20 100 100
select values in J.lSecthat correspond
to your spectrometer's pulse angle of
90 degrees 60 degrees
1.000 3.362
1000 5000
60.010 15.091
NA 60.010
4.096 1.638
NA
3.362
5000
15.091
60.010
1.638
Data Processing
The NMRdata processing program WinNUTSincludes a number of data processing MACROSdeveloped by Aii specifically for
the EFT series spectrometers. The number of operations included within a MACROand the sequence in which they're executed
is a function of the NMRdata acquisition sequence, i.e. 'H survey spectrum, DEPT, COSy, T" etc. A license for WinNUTS (Acorn
NMR, Inc., Freemont, California) is provided as a standard component of the EFT series NMRsoftware operating system
Anasazi Instruments, Inc. 4101 CashardAvenue Indianapolis, Indiana 46203 (317) 783 - 4126
providing pradical & affordable FT-NMRsolutions for the undergraduate laboratory
.