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CH203 Fall 2014 NMR Practice Quiz



1. Consider the
1
H NMR spectrum below


a. How many types of hydrogen are present, assuming no serious overlap between different
types? _____

b. What is the chemical shift of the hydrogen type that is most shielded? ______

c. Consider the multiplicity, which derives from spin-spin coupling. What best describes the
most shielded hydrogen type?
____Singlet
____Doublet
____Triplet
____Quartet
____Doublet of doublets

d. What does this multiplicity indicate about the most shielded hydrogens?
_____There is one hydrogen present at this position
_____There are two hydrogens present at this position
_____There are three hydrogens present at this position
_____There are two hydrogens on the neighboring carbon
_____There are three hydrogens on the neighboring carbon

e. If the molecular formula of the compound is C
3
H
7
Br, what does the integration show about the
most shielded hydrogens?
_____There is one hydrogen present at this position
_____There are two hydrogens present at this position
2
_____There are three hydrogens present at this position
_____There are two hydrogens on the neighboring carbon
_____There are three hydrogens on the neighboring carbon

f. What can you conclude about the most shielded hydrogens, using the above evidence?
_____They represent a CH2 group, attached to another CH2.
_____They represent a CH2 group, attached to a CH3.
_____They represent a CH3 group, attached to a CH2.
_____They represent a CH3 group, attached to another CH3.
_____They represent a CH2 group, attached to CH.

g. What is the chemical shift of the hydrogen type that is most deshielded?
_____

h. Knowing that the formula for this compound is C
3
H
7
Br, what does the chemical shift of these
deshielded hydrogens suggest?
_____There is an aromatic ring attached at this position
_____There is a bromine attached at this position
_____The aromatic ring is at the other end of the molecule
_____The bromine is at the other end of the molecule

i. How many hydrogens are present at this deshielded position?
_____1
_____2
_____3
_____4
_____5

j. How many hydrogens are present on the carbon adjacent to the deshielded position?
_____1
_____2
_____3
_____4
_____5

2. When an external magnetic field is applied, what happens to the protons in a sample?
_____All protons align with the field.
_____All protons align opposite to the field.
_____Some protons align with the field and some align opposite to it.
_____All protons assume a random orientation.


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3. Which of the following compounds gives a
1
H NMR spectrum consisting of only a singlet,
triplet and quintet?
_____CH
3
OCH
2
CH
2
CH
2
CH
2
OH
_____CH
3
OCH
2
CH
2
OCH
2
CH
3

_____CH
3
OCH
2
CH
2
CH
2
OCH
3

_____CH
3
OCH
2
CH(CH
3
)OCH
3


4. What is the splitting pattern of the methylene protons in propane?
_____triplet
_____quartet
_____doublet
_____septet

5. A compound of formula C5H12 gives 1 signal in the 1H NMR and 2 signals in the 13C NMR.
The compound is
_____pentane.
_____2-methylbutane.
_____2,2-dimethylpropane.
_____Cannot tell without more information.

6. There are several compounds with the
molecular formula C5H10Br2. Which isomer
ad with this formula has the following 1H NMR
spectrum?
! (ppm) 1.0 (9H, singlet), 5.3 (1H, singlet)

_____a
_____b
_____c
_____d

7. Which of the following combinations of peaks appears in the 1H NMR spectrum of 1,4-
dimethyoxyethane, CH3OCH2CH2CH2CH2OCH3?
_____three singlets
_____a singlet, a triplet, and a quintet
_____a singlet and two triplets
_____a doublet and a triplet



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8. Propose a structure for the compound C
7
H
9
N with the spectra below



3. (25 points total) Answer the questions below about the structure that has MW = 107
and the following NMR spectra:
5
0 1 2 3 4 5 6 7 8 9 10
2 H, J=7.9 HZ
1 H, J=7.9 HZ
PPM
6 H,s
200 180 160 140 120 100 80 60 40 20 0
PPM
Figure by MIT OCW.
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9. Propose a structure for the compound C
8
H
8
O
2
with the spectra below
1H NMR 3.75 ppm (s, 6H), 6.83 ppm (s, 4H)
13C NMR 153, 114, and 56 ppm



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10. Which C
9
H
10
O compound gives the following
1
H NMR spectrum?


11. Identify the compound (C
4
H
8
O) that gives the following
1
H NMR spectrum.




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12. Predict the features expected in the
1
H NMR for the compound shown by completing the
table below. (Label equivalent sets of protons H
a
, H
b
, etc. for clarity.)




protons type approximate
ppm
multiplicity J
nm
(Hz) reason for J integral
H
a

H
b

H
c

H
d

H
e



Assign each
13
C signal seen in the NMRs of the compounds below to the carbon giving rise to
the signal.

13.

1. 165 ppm
2. 147 ppm
3. 87 ppm
4. 42 ppm








14.

1. 81 ppm
2. 30 ppm





O
O
H
2
C
O
Cl
Cl
8

15.

1. 176 ppm
2. 170 ppm
3. 134 ppm
4. 131 ppm
5. 38 ppm
HO
O
CH
2
OH
O

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