Chapter 14: Q 14-14-63 E (page 447)
Dimethyl butynedioate also undergoes a Diel-Alder reaction with (2E, 4Z)-2,4-hexadiene, but the stereochemistry of the product is different from that of the (2E,4E) isomer (Problem 14-62). Explain.
Short Answer

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Chapter 14: Q 14-14-63 E (page 447)
Dimethyl butynedioate also undergoes a Diel-Alder reaction with (2E, 4Z)-2,4-hexadiene, but the stereochemistry of the product is different from that of the (2E,4E) isomer (Problem 14-62). Explain.

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Hydrocarbon A, C10H14 , has a UV absorption at and gives hydrocarbon B, C10H18, on catalytic hydrogenation. Ozonolysis of A, followed by zinc/acetic acid treatment, yields the following diketo dialdehyde:

b)Hydrocarbon A reacts with maleic anhydride to yield a Diels-Alder adduct. Which of your structures for A is correct?
Dimethyl butynedioate undergoes a Diels-Alder reaction with (2E,4E)-2,4-hexadiene. Show the structure and stereochemistry of the product.

Draw the resonance forms that result when the dienes below are protonated. If the resonance forms differ in energy, identify the most stableone.
a)
b)
c)
Show the structure, including stereochemistry, of the product from the following Diels-Alder reaction:
Which of the following compounds would you expect to have a
UV absorption in the 200 to 400 nm range?
a)

b)

c)

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