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.
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.
Chapter1: Taking Risks And Making Profits Within The Dynamic Business Environment
Section: Chapter Questions
Problem 1CE
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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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