4. Use the NMR chemical shifts table provided in the lecture slides to answer the following questions. a. Briefly rationalize, based on chemical fundamentals and the physics of NMR chemical shift, why the aldehyde proton is at 9.5 ppm, the chloromethyl proton at-3.5 ppm, and a standard methyl proton at 1 ppm. A good answer should be -4-6 sentences. b. A compound "A" of chemical formula C3H6CI2 has the NMR spectrum below. What is its structure? Briefly explain your reasoning.

EBK A SMALL SCALE APPROACH TO ORGANIC L
4th Edition
ISBN:9781305446021
Author:Lampman
Publisher:Lampman
Chapter96: Carbon-13 Nuclear Magnetic Resonance Spectroscopy
Section: Chapter Questions
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Use the NMR chemical shifts table provided in the lecture slides to answer the following
questions.
4.
Briefly rationalize, based on chemical fundamentals and the physics of NMR chemical
shift, why the aldehyde proton is at 9.5 ppm, the chloromethyl proton at 3.5 ppm, and
a standard methyl proton at - 1 ppm. A good answer should be ~ 4 – 6 sentences.
a.
b.
A compound "A" of chemical formula C3H&Cl2 has the NMR spectrum below. What is its
structure? Briefly explain your reasoning.
B - 3.75
A = 2.20
TMS
1.90 Hz
6.
5
4.
3
1
O s ppm
c. Compound A can form polymers by reacting with H2N-CH2-CH2-CH2-NH2. What is the
mechanism of the polymerization reaction?
d. Draw the mechanism for the formation of a monomer unit using the arrow formalism.
Will this reaction yield only linear polymers (like Nylon) or will it also yield branching?
Briefly explain your answer. Draw arrows for reaction if necessary.
e.
Transcribed Image Text:Use the NMR chemical shifts table provided in the lecture slides to answer the following questions. 4. Briefly rationalize, based on chemical fundamentals and the physics of NMR chemical shift, why the aldehyde proton is at 9.5 ppm, the chloromethyl proton at 3.5 ppm, and a standard methyl proton at - 1 ppm. A good answer should be ~ 4 – 6 sentences. a. b. A compound "A" of chemical formula C3H&Cl2 has the NMR spectrum below. What is its structure? Briefly explain your reasoning. B - 3.75 A = 2.20 TMS 1.90 Hz 6. 5 4. 3 1 O s ppm c. Compound A can form polymers by reacting with H2N-CH2-CH2-CH2-NH2. What is the mechanism of the polymerization reaction? d. Draw the mechanism for the formation of a monomer unit using the arrow formalism. Will this reaction yield only linear polymers (like Nylon) or will it also yield branching? Briefly explain your answer. Draw arrows for reaction if necessary. e.
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