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Christopher M.

Hadad Chemistry 253 Spring 2001

Quiz - May 3, 2001

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There is 1 page and 15 pts on this quiz. Please read each question carefully before answering.

1. (6 pts) Determine the number of different kinds of protons in each compound that would be observed by 1H NMR.

(a) 1-chloropropane
H H
the CH3 group is unique
H 3C 3 unique H's in the proton NMR
Cl the CH2 group between CH3 and CH 2 is unique
the CH2 group attached to Cl is unique
H H
(b) 2-chloropropane
Cl
each CH3 group is identical to the other CH 3 group
H 3C CH3 the CH group is unique 2 unique H's in the proton NMR
H

(c) 1-bromo-2-methylbenzene
Br
H CH3
each H is unique as each is in a different
chemical environment 5 unique H's in the proton NMR

H H

H
2. (9 pts) Tell precisely how you would use the proton NMR spectra to unambiguously distinguish between the following
pairs of compounds.
O O
H 3C
(a) H and H 3C CH3
A B
A would have 3 distinct peaks in the 1H NMR: a C(=O)ÐH peak at δ 9-10 ppm, a CH2 peak at δ 2.1 ppm (as a quartet),
and a CH3 peak at δ 1.0 ppm (triplet). B would have only one peak in the 1H NMR: a singlet at δ 2.1 ppm for the CH3.

O O
(b) and H 3C CH3
H 3C O CH3 O
C D
C would have 3 peaks in the 1H NMR, and so would D. The number of peaks is not a distinguishing feature. The
chemical shift of the peaks and their multiplicity is very different, however. In C, there will be a singlet for the CH3
group next to the C=O group at δ 2.1 ppm as a singlet, and the CH2 group will appear at δ 3.5 ppm as a quartet. In D, the
CH3 group adjacent to the O comes at δ 3.5 ppm as a singlet. And the CH2 group appears at δ 2.1 ppm as a quartet.

(c) CH3CH2 C C H and CH3 C C CH3


E F
In E, there is an alkynyl C-H peak at δ 2.5 ppm, and 2 distinct signals for a typical ethyl group (peaks for CH2 and CH3
groups). In F, there will only be one peak in the 1H NMR at about δ 2.4 ppm (due to the symmetry in the molecule).

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