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b) (5 pts] Redraw compound C showing the correct stereochemistry for the labelled hydrogens based on the Woodward-Hoffman selection rules. 2. Photolysis of diene A

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b) (5 pts] Redraw compound C showing the correct stereochemistry for the labelled hydrogens based on the Woodward-Hoffman selection rules. 2. Photolysis of diene A below in benzene leads to eventual formation of 1,2,3,4-tetrahydronaphthalene and 1,3-butadiene (A. Gilbert and R. Walsh, J. Am. Chem. Soc., 1976, 98, 1606). The mechanism is believed to follow a cascade of five sequential pericyclic reactions. The structures of all intermediates B to F have been drawn in for you. 1 3 3 2 2 benzene 4 b 4 a 5 e 5 5 b hy step 1 step 2 8 6 8 d 6 8 6 B C step 3 3 a a 4 b 3 b 5 1 4 4 e 6 e step 5 5 1 5 step 4 7 d 8 1 6 7 8 d 6 8 de E D

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