Assignment #23

Chemistry 3231, Fall 2014

Complete by Thursday, October 9
1. Determine whether the following sets of groups are chemically equivalent (homotopic) or not.
H

OH

CH3

CH3
H 3C

CH3

The two Me
groups of acetone

CH3
F

The three hydrogens

of the toluene methyl group

The two Me groups

of o-ethyltoluene

The two
fluorines above

H
H

The two hydrogens

highlighted above

2. In the following molecules, label the sets of homotopic (i.e., chemically equivalent) hydrogens
(the first structure shows an example).
Cl

a
H3C

a
CH3

c
Example
Three different sets
of hydrogens

CH3
CH3

H 3C

CH3

H3C

CH3

H 3C
H3C

H
H

3. For each of the following molecules, determine whether the two methyl groups are homotopic,
enantiotopic, or diastereotopic.
Cl

Cl
Cl

H3C
H3C

H3C
H3C

H3C
H3C

4. One indicator of aromaticity is observation of ring current NMR effects. For example, as you
saw at the end of Mondays lecture, with benzene the downfield chemical shift of the aromatic
protons is attributable to a current induced in the -system of the aromatic ring. In the region
occupied by the phenyl Hs, this small induced magnetic field reinforces the external field,
leading to pronounced downfield shift of the signal for the 1H nuclei (see Klein 2nd Ed., Figure
16.9). The 1H NMR spectrum of [18]-annulene (1, below) shows signals at 9 (integral = 2) and
3 (integral = 1). How does this NMR data support the notion that [18]-annulene is aromatic?
Does this make sense in view of the Hckel rule? Making a picture analogous to the one from
the end of Mondays lecture or that of Kleins Figure 16.9 will be helpful.
H
18

H
H

H
14

H
1

H
H

H
H

H
H

H
8

Textbook resources: Klein (2nd Ed.) 16.1 Introduction to NMR Spectroscopy;16.2 Acquiring a 1H
NMR Spectrum; 16.3 Characteristics of a 1H NMR Spectrum; 16.5 Chemical Shift
Thursday office hour: 10:00-11:00, Alt 806