54. A chemist wanted to make the ethyl ester of 2-formylbenzoic acid using the reagents listed below. The IR of the final product showed an ester, but no aldehyde absorption and no absorption in the OH region. Use the spectra below to determine what the chemist made. HO. C H + HNMR chemical shifts 8.0-8.4 ppm 4H, complex 10.4 ppm1H sharp singlet 13.3ppm 1H broad singlet 1.1 ppm 3H triplet OH H* catalyst X C10H 100 3 + H₂O HNMR chemical shifts 7.5-7.8 ppm 4H complex 6.6 ppm 1H sharp singlet 3.9 ppm 2H quartet

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
Section24.SE: Something Extra
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54. A chemist wanted to make the ethyl ester of 2-formylbenzoic acid using the reagents
listed below. The IR of the final product showed an ester, but no aldehyde absorption and
no absorption in the OH region. Use the spectra below to determine what the chemist
made.
НО.
ze
+
HNMR chemical shifts
8.0-8.4 ppm 4H, complex
10.4 ppm1H sharp singlet
13.3ppm 1H broad singlet
1.1 ppm 3H triplet
OH
H*
catalyst
X
C10H1003
+
H₂O
HNMR chemical shifts
7.5-7.8 ppm 4H complex
6.6 ppm 1H sharp singlet
3.9 ppm 2H quartet
Transcribed Image Text:54. A chemist wanted to make the ethyl ester of 2-formylbenzoic acid using the reagents listed below. The IR of the final product showed an ester, but no aldehyde absorption and no absorption in the OH region. Use the spectra below to determine what the chemist made. НО. ze + HNMR chemical shifts 8.0-8.4 ppm 4H, complex 10.4 ppm1H sharp singlet 13.3ppm 1H broad singlet 1.1 ppm 3H triplet OH H* catalyst X C10H1003 + H₂O HNMR chemical shifts 7.5-7.8 ppm 4H complex 6.6 ppm 1H sharp singlet 3.9 ppm 2H quartet
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