Chapter 14: 33E (page 447)
Show the structure, including stereochemistry, of the product from the following Diels-Alder reaction:
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Chapter 14: 33E (page 447)
Show the structure, including stereochemistry, of the product from the following Diels-Alder reaction:
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Answer the questions below for 1,3,5-cycloheptatriene.
(a)How many patomic orbitals are in the conjugated system?
(b)How many molecular orbitals describe the conjugated system?
(c)How many molecular orbitals are bonding molecular orbitals?
(d)How many molecular orbitals are anti-bonding molecular orbitals?
(e)Which molecular orbitals are filled with electrons?
(f)If this molecule were to absorb a photon of UV light an electron would move between which two molecular orbitals (be specific)?
How could you use Diels-Alder reactions to prepare the following products ? Show the starting diene and dienophile in each case.
a)

Hydrocarbon A, , has a UV absorption at =236nm and gives hydrocarbon B, C10H18, on catalytic hydrogenation. Ozonolysis of A, followed by zinc/acetic acid treatment, yields the following diketo dialdehyde:

a)Propose two possible structures for A.
How could you use Diels-Alder reactions to prepare the following products ? Show the starting diene and dienophile in each case.
c)

Di-tert-butyl-1,3-butadiene does not undergo Diels-Alder reactions. Explain.
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