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Problem Set #6 Answers

1. This document provides NMR data for the assignment of protons on a substituted naphthalene compound. It includes the chemical shift, multiplicity, and coupling constants for each proton. 2. For proton H3, a stick diagram of the multiplet is drawn showing the correct intensities of the peaks. 3. The conformation is determined to be equatorial based on the large geminal coupling for proton H4 and its axial couplings to protons H3 and H7, indicating the CH2CO2H substituent is equatorial. 4. The proton at 9.3 ppm is assigned and circled on the structure.

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87 views3 pages

Problem Set #6 Answers

1. This document provides NMR data for the assignment of protons on a substituted naphthalene compound. It includes the chemical shift, multiplicity, and coupling constants for each proton. 2. For proton H3, a stick diagram of the multiplet is drawn showing the correct intensities of the peaks. 3. The conformation is determined to be equatorial based on the large geminal coupling for proton H4 and its axial couplings to protons H3 and H7, indicating the CH2CO2H substituent is equatorial. 4. The proton at 9.3 ppm is assigned and circled on the structure.

Uploaded by

Stefan Bam
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Chemistry 4953/6973 NMR Spectroscopy Name ___________________________

Problem set 6

1)
sol 1 sol 2
Jab 11.7 11.4
Jax 8.12 -4.29
Jbx 2.98 15.39
A 1150.85 3.84
 1141.00 3.80

2)

sol 1 sol 2
Jab 12.5 12.5
Jax 0.04 8.44
Jbx 8.44 0.04
A 1146.32 3.82 1142.08 3.81
 1142.08 3.81 1144.32 3.82
Problem R-05F (C16H14O3) This problem requires you to assign some of the protons of a
substituted naphthalene, and determine the conformation. You may use first order analysis.
H
H H
O O
H4
O
O H4
H H6
6 H2 H1 H3
H
OH H5
H 5
H H7 H2
7 CO 2H CO2H
H H3 H1
H
(a) For each proton give the chemical shift (), the multiplicity (e.g. dtq) and the coupling constants.
H2 H4

H5

2.55 2.50 2.45 2.40 2.35 2.30 2.25 2.20 2.15 2.10 2.05 2.00

 mult. Coupling constants 30 20 10 0 H1


1 H 1 2.49 dd 16.5, 6.5

1 H2 3.01 dd 16.5, 6.0


H7 Hz
2 6
H3 3.18 dtd 13.5, 6.5, 4.5 H3 H

1 H4 2.06 tdd 13.5, 12.5, 4.5 (almost qd)

1 H5 2.30 dtd 13.5, 4.5, 3.0

2 H6 3.12 ddd 17.5, 4.5, 3.0 3.35 3.30 3.25 3.20 3.15 3.10 3.05 3.00 2.95

2 H7 3.27 ddd 17.6, 12, 5.0

3 (b) A key signal is the one for H3. Draw a stick diagram (with correct intensities) of the multiplet
for H3 above or below the appropriate peaks.

(c) Circle the correct conformation, and briefly explain how you made the assignment. Be specific.

5 The proton H4 has three large couplings - one is the gem (12.5) and the other two (13.5 and 12.5) are to the
axial prons H 7 and H3. Thus the CH2CO2H substituent is equatorial.

(d) Assign the proton at  9.3 (circle it on the structure).

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