CHEM220 SI Mini Revision Test

23 May 2023
NMR and Stereochemistry

Section A – Multiple Choice Questions

For questions 1-3 refer to the structure below:

1. How many resonances would you expect to see in the 1H NMR spectrum of this
molecule?
a. 4
b. 3
c. 7
d. 5
2. The multiplicity and proton integration of the most upfield signal would be.
a. 1H,singlet
b. 2h, triplet
c. 3H, doublet
d. 1H, pentet
3. The multiplicity and proton integration of the most downfield signal would.
a. 2H, triplet
b. 1H, pentet
c. 3H, doublet
d. 1H, quartet
4. The use of tetramethylsilane ((CH3)4Si, TMS) as a reference in 1H NMR relies on the
fact that
a. silicon can form 4 bonds
b. the four methyl groups in TMS are equivalent
c. silicon is more electronegative than carbon, resulting in the TMS methyl signals
appearing downfield of (most) carbon-bonded H’s
d. silicon is less electronegative than carbon, resulting in the TMS methyl signals
appearing upfield of (most) carbon-bonded H’s
5. A compound of molecular formula C9H12 gives a 1H NMR spectrum with only one
upfield (δ 2.25) and one downfield (δ 7.25) singlet signals, with a proton integration
ratio of 3:1. The most likely structure for this compound is:

6. The effect which causes the signals of aromatic protons to appear much further
downfield than expected, given the electron-rich nature of an aromatic ring, is known
as:
a. diamagnetic resonance
b. diamagnetic anisotropy
c. diamagnetic shielding
d. diamagnetic excitation
7. Identify a statement that best describes the proton NMR spectrum of the following
molecule.
CH3CH2C(O)CH2CH3
a. A triplet at 2.8 ppm and a quartet at 1.3 ppm
b. A triplet at 1.3 ppm and a quartet at 2.8 ppm
c. Two triplets at 2.8 ppm and two quartets at 1.3 ppm and a singlet at 3.0 ppm
d. A triplet at 2.8 ppm and a quartet at 1.3 ppm and a singlet at 3.0 ppm
8. The intensities of a quartet are in the ratio:
a. 1:3:3:1
b. 2:3:3:2
c. 1:3:1:3
d. 1:4:4:1
9. The spectrum below belongs to a molecule with the molecular formula C5H9ClO2. The
following structure can be deduced from this spectrum:
 a. CH3O-CH2CH2-C(O)CH2Cl
b. CH3CH2O-C(O)CH2CH2Cl
c. CH3CH2O-CH2-C(O)CH2Cl
d. CH3CH2CH2O-CH2C(O)Cl
10. Identify the statement below that is not true of enantiomers
a. They have the same physical properties
b. They are bonded to four different groups
c. They have the same chemical properties
d. They interact with plane polarised light the same
11. The following method is employed to separate enantiomers.
a. Recrystallization
b. normal adhesion chromatography with silica as a packing material
c. adhesion chromatography packed with a chiral packing material
d. fractional distillation
12. A mixture of S-(+)-2-bromobutane and R-(-)-2-bromobutane has an optical rotation of
+ 8.2ᵒ. The specific rotation of S-(+)-bromobutane is +32.8ᵒ. Choose the correct
statement from those given below:
a. A racemic mixture exists
b. The enantiomeric excess of the R-(-) isomer is 25%
c. There is more of the R-(-) isomer than the S-(+) isomer
d. There is more of the S-(+) isomer than the R-(-) isomer
13. A molecule with 3 chiral centres can have up to
a. 2 diastereomers
b. 8 diastereomers
c. 4 diastereomers
d. 16 diastereomers
14. A sample of enantiomerically pure (S)-(+)-2-bromobutane has a specific rotation of
+30.0ᵒ. A sample containing the two isomers has an observed specific rotation of 23.1ᵒ,
this implies that:
a. The R-(-)-isomer is in excess
b. The R-(+)-isomer is in excess
c. The S-(+)-isomer is in excess
d. The S-(-)-isomer is in excess
15. Pure R-2-iodobutane has a specific rotation of - 46.0ᵒ. A 30 g sample of 2-iodobutane
has an observed optical rotation of -11.0ᵒ. The following is true about the sample.
a. It contains 11.413 g of the R-2-iodobutane isomer
b. It contains 18.587 g of the R-2-iodobutane isomer
c. It contains 7.431 g of the R-2-iodobutane isomer
d. It contains R-2-iodobutane in 39.5% enantiomeric excess
Section B-Long Questions
1. You have been provided with an NMR spectrum for an unknown compound with a
molecular formula of C5H9O2Br. Using the NMR spectrum assign a plausible
structure to account for the observed signals. (NOTE: marks will be awarded for
your workings and you may annotate on the NMR spectrum provided.)
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Sigma-Aldrich Co.

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2. Name the following molecule as R or S, showing all working for your answer:

3. i. Draw all possible diastereomers for the following molecule using the Fischer
projection with the carbon backbone on the vertical axis.
ii. Identify the pairs of enantiomers.