CHEM220 REVISION

19 May 2022

1. A compound that rotates the plane of polarised light to the left is

a) said to be levorotatory
b) denoted by the symbol (+)
c) preceded by the symbol S
d) said to be dextrorotatory

2. A mesomer is

a) a molecule with two chiral centres where one chiral centre is R and the other is S.
b) a molecule with two or more chiral centres that does not have a plane of symmetry.
c) a molecule with two chiral centres where each of the chiral carbons are bonded to the
same four groups.
d) a compound with two or more chiral centres whose mirror image is superimposable on
itself.

3. Which of the following statements best describe the 1H NMR spectrum of the following
molecule: C(O) represents carbonyl
CH3CH2C(O)CH2CH3
a) A triplet at 2.5 ppm, a quartet at 1.0 ppm and a singlet at 2.8 ppm
b) A triplet at 1.0 ppm and a quartet at 2.5 ppm
c) A triplet at 2.5 ppm and a quartet at 1.0 ppm
d) Two quartets at 2.5 ppm and 2.8 ppm, and two triplets at 1.0 ppm and 1.2 ppm

4. A chiral molecule is a molecule that

a) has a hydrogen atom as its lowest priority group

b) has no plane of symmetry
c) has four different groups around the central carbon
d) is superimposable on its mirror image
5. The specific rotation of a pure (+) substance has an optical rotation of + 0.55º. What
is the observed specific rotation of a mixture containing 60% of (+) isomer and 40%
of the (-) isomer?

a) + 0.33º
b) + 0.22º
c) + 0.44º
d) + 0.11º

6. Enantiomers are

a) mirror images of a molecule without symmetry

b) mirror images of a molecule with symmetry
c) mirror images of a molecule with an achiral centre
d) mirror images of a molecule with a chiral centre

7. The intensities of a triplet are in the ratio:

a) 1:3:1
b) 1:4:1
c) 1:2:1
d) 2:3:2

8. 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.
a) It contains 11.413 g of the R-2-iodobutane isomer
b) It contains 7.431 g of the R-2-iodobutane isomer
c) It contains 18.587 g of the R-2-iodobutane isomer
d) It contains R-2-iodobutane in 39.5% enantiomeric excess

9. A mixture of S-(+)-2-bromobutane and R-(-)-2-bromobutane has an optical

rotation of + 30.8º. The specific rotation of pure R-(-)-2-bromobutane is -44.0º.
Choose the correct statement from those given below:

a) The mixture contains 30% S-(+)-2-bromobutane

b) The mixture contains 70% S-(+)-2-bromobutane
c) The mixture contains 70% S-(+)-2-bromobutane
d) The mixture contains 15% S-(+)-2-bromobutane
10. How many resonances would you expect to see in the proton NMR of the
following molecule?

a) 3
b) 6
c) 4
d) 2

11. 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-CH2-C(O)CH2Cl
c) CH3CH2O-C(O)CH2CH2Cl
d) CH3CH2CH2O-CH2C(O)Cl

12. The intensities of a quartet are in the ratio:

a) 1:3:3:1
b) 2:3:3:2
c) 1:4:4:1
d) 1:3:1:3