Understanding Business
Understanding Business
12th Edition
ISBN: 9781259929434
Author: William Nickels
Publisher: McGraw-Hill Education
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3. (10 pt, graduate) The following reaction between a phosphorus ylid and an aldehyde gives a
hydrocarbon, C10H13, with the following ¹H and 13C NMR spectral data. Give the structures of
both starting aldehyde and product alkene. Use spectral data to support your answer and
comment on the stereochemistry of the product based on the coupling constant values.
+
-PPh3
+
Aldehyde
Product +
Ph3P=0
1H NMR (CDCl3, 500 MHz): 8 7.22 (2H, d, J = 8.0 Hz), 7.09 (2H, d, J = 8.0 Hz), 6.36 (1H, d, J = 16.0 Hz), 6.18
(1H, dq, J = 16.0, 6.3 Hz), 2.32 (3H, s), 1.86 (3H, d, J = 6.9 Hz)
13C{1H} NMR (125 MHz, CDC13): 8 136.4, 135.2, 130.9, 129.2, 125.8, 124.7, 21.2, 18.5.
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Transcribed Image Text:3. (10 pt, graduate) The following reaction between a phosphorus ylid and an aldehyde gives a hydrocarbon, C10H13, with the following ¹H and 13C NMR spectral data. Give the structures of both starting aldehyde and product alkene. Use spectral data to support your answer and comment on the stereochemistry of the product based on the coupling constant values. + -PPh3 + Aldehyde Product + Ph3P=0 1H NMR (CDCl3, 500 MHz): 8 7.22 (2H, d, J = 8.0 Hz), 7.09 (2H, d, J = 8.0 Hz), 6.36 (1H, d, J = 16.0 Hz), 6.18 (1H, dq, J = 16.0, 6.3 Hz), 2.32 (3H, s), 1.86 (3H, d, J = 6.9 Hz) 13C{1H} NMR (125 MHz, CDC13): 8 136.4, 135.2, 130.9, 129.2, 125.8, 124.7, 21.2, 18.5.
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