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NMR Worksheet 2

This document contains questions pertaining to analyzing 1H NMR spectra. It asks the student to: 1) Label different types of hydrogen atoms in a sample compound. 2) Explain why one hydrogen atom is most downfield based on chemical environment. 3) Analyze a 1H NMR spectrum and explain the observed multiplicities of resonances using spin-spin coupling concepts.

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Shyam Bhakta
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149 views5 pages

NMR Worksheet 2

This document contains questions pertaining to analyzing 1H NMR spectra. It asks the student to: 1) Label different types of hydrogen atoms in a sample compound. 2) Explain why one hydrogen atom is most downfield based on chemical environment. 3) Analyze a 1H NMR spectrum and explain the observed multiplicities of resonances using spin-spin coupling concepts.

Uploaded by

Shyam Bhakta
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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!"#$ &&'() *+,, '-&') .

/0 12345"##6 7' Name:___________________uSI___________________


!"# %&'( )* +, -#./"0# 1, 2"#34)56 718#*9#0 :; <1" *)5 =10> +, 3*)?? @01"A3 B10 /C+3
)33+@,*#,/;

89#56:2; &
The following questions peitain to compounu (:

(a) Reuiaw ( below anu label the uiffeient types of hyuiogen atoms. 0se BA foi the most
uownfielu etc.





(b) Why is BA the most uownfielu hyuiogen atom.





(c) A iepiesentation of the
1
B NNR spectium foi ( is shown below. 0sing the B! anu B"
notations that we uiscusseu in lectuie, explain why the multiplicities (i.e., tiiplet anu
quaitet) that aie shown aie obseiveu foi each of the iesonances at 2.u9 ppm anu S.68 ppm .







Cl
Cl Cl
A
0 1 2 3 4 5 6
PPM















































89#56:2; '
Spin-spin coupling is not obseiveu foi hyuiogen atoms on caibon atoms that aie sepaiateu
by a heteioatom (e.g., 0 oi N). These hyuiogen atoms aie saiu to exist in uiffeient spin
systems. Foi example, foi methylethyl ethei, the following assignments can be maue:

.26#: The integiateu +3#+ of each of the multiplets (shown in ieu) ieflects the numbei of
hyuiogen atoms at the iesonance.
Pieuict the
1
B NNR spectium that you woulu expect foi methyl piopanoate shown below.
(0se Table 8.S to estimate chemical shifts). Show integiations in squaie biackets below each
iesonance.














H
C
O H
B
H
C
H
C
H
A
H
A
H
B
H
B
Methylethyl ether
0 1 2 3 4
PPM
H
C
H
A
H
B
[2] [3] [3]
O
O
Methyl propanoate
89#56:2; <=
The iatios of the signals that compiise the multiplicities foi uiffeient iesonances can be
pieuicteu using Pascal's tiiangle (Figuie 8.12, page 1S4)

List the iatios that you woulu expect foi the following multiplicities
Boublet:
Tiiplet:
Quaitet:
Quintet:

These iatios as well as the multiplicities can also be ueteimineu using splitting tiees. To use
a splitting tiee, it is impoitant to know the coupling constants (D), which was intiouuceu at
the enu of lectuie. Foi example, lets consiuei compounu > below:

uiven that the coupling constant between BA anu BB is 6 Bz (i.e., DAB = 6 Bz), let us use a
splitting tiee to pieuict the multiplicity of BA.


0se a splitting tiee, pieuict the multiplicity of BB anu uiaw this iesonance (each box
iepiesents 1 Bz)

Br Br
H
B
H
B
H
A
H
A
H
A
B
1 2 1
6 Hz
6 Hz 6 Hz
H
A
is a Triplet

89#56:2; ?
Foi compounu !

Pieuict its
1
B NNR spectium by iuentifying the uiffeient types of hyuiogen atoms, theii
expecteu chemical shifts, anu use a splitting tiee to pieuict the multiplicities foi each
iesonance (each box iepiesents 1 Bz). Assume coupling constants aie 6 Bz.






O O
C

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