draw the structure of a compound with the molecular formula c9h10o2 that produces the following 1h nmr spectrum and 13c nmr spectrum.
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Exam 2 Answer Key
Organic Chemistry IIChem 335 - Winter 2008
Exam 2 Answer Key1. (15 points) Write clear structures for each of the following:a) (Z),(R)-4-hexen-2-olb) a chromate esterc) an isobutyl Gilman reagentd) the periodic acid cleavage products from 1,2-propanediole) sodium 4-nitrobenzenethiolate2a. (5 points) Draw a typical quartet from a proton NMR spectrum and show where the chemical shift (d) and the coupling constant (J) would be measured.
Illustrate what this means in terms of the stereochemistry of the product expected from cyclopentene. Draw the product(s) expected and designate stereochemistry with R and S.
2d. (5 points) The formation of a vicinal diol using tBuOOH and OsO4 is a syn addition.Illustrate what this means in terms of the stereochemistry of the product expected from
cis-2-butene. Draw the product(s) expected and designate stereochemistry with R and S.
3. (15 points) Complete each of the following reactions by writing the structure of the expected product:a) b) c) d)
a 9.9 ppm , 1 H , singlet
b 7.8 ppm , 2 H , doublet
c 6.9 ppm , 2 H , doublet
d 4.1 ppm , 2 H , quartet
e 1.4 ppm , 3 H , triplet
Identify by letter on your final structure each of the H absorptions above.
additional peaks at 107 & 109 (equal intensity)
largest peak at 59
13C NMR: peaks at 70, 66, 30, and 15 ppm1H NMR :a 3.7 ppm , 2 H , triplet
b 3.5 ppm , 2 H , quartet
c 3.4 ppm , 2 H , triplet
d 1.2 ppm , 3 H , triplet
Identify by letter on your final structure each of the H absorptions above.Identify each of the 13C peaks by reference to your structure.Identify each of the peaks in the mass spectrum.
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Solution for Draw the structure of a compound with the molecular formula CşH;0Oz that produces the following 'H NMR spectrum and 13C NMR spectrum. Proton NMR 12…
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Draw the structure of a compound with the molecular formula CşH;0Oz that produces the following 'H NMR spectrum and 13C NMR spectrum. Proton NMR 12 11 10 7 6 5 3 Chemical Shift (ppm) Carbon NMR 128.8- -128.4 126.8 35.8 30.7 179.9 140.4 180 160 140 120 100 80 40 20 Chemical Shift (ppm) -2.
Draw the structure of a compound with the molecular formula CşH;0Oz that produces the following 'H NMR spectrum and 13C NMR spectrum. Proton NMR 12 11 10 7 6 5 3 Chemical Shift (ppm) Carbon NMR 128.8- -128.4 126.8 35.8 30.7 179.9 140.4 180 160 140 120 100 80 40 20 Chemical Shift (ppm) -2.
Question
Draw the structure of a compound with the molecular formula C9H10O2 that produces the following 1H NMR spectrum and 13C NMR spectrum.
Transcribed Image Text:Draw the structure of a compound with the molecular formula CóH1002 that produces the following 'H NMR spectrum and 13C NMR spectrum. Proton NMR 12 11 10 7 6 5 3 Chemical Shift (ppm) Carbon NMR 128.8- -128.4 126.8 35.8- -30.7 -179.9 140.4 180 160 140 120 100 80 60 40 20 Chemical Shift (ppm) 2.
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