Chapter 14: Q14-17E (page 447)
Show the product of the Diels–Alder reaction of the following dienewith 3-buten-2-one, H2C=CHCOCH3. Make sure you show the fullstereochemistry of the reaction product.

Short Answer

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Chapter 14: Q14-17E (page 447)
Show the product of the Diels–Alder reaction of the following dienewith 3-buten-2-one, H2C=CHCOCH3. Make sure you show the fullstereochemistry of the reaction product.


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If pure vitamin A has =5 325 (= 50,100), what is the vitamin A concentration in a sample whose absorbance at 325 nm is A = 0.735 in a cell with a path length of 1.00 cm?
Draw and name the six possible diene isomers of formula. Which of the six are conjugated dienes?
Luminol, which is used by forensic scientists to find blood, fluoresces as a result of Diels-Alder like process. The dianion of luminal reacts with to form an unstable peroxide intermediate that then loses nitrogen to form a dicarboxylate and emit light. The process is similar to that in 14-21 and 14-22. Propose a mechanism for this process.

Which of the following compounds would you expect to show ultraviolet absorptions in the 200 to 400 nm range?

An extremely useful diene in the synthesis of many natural products is
known as Danishefsky’s diene. This compound is useful because after
the Diels–Alder reaction it can be converted into a product that could
not be accessed by a typical Diels–Alder reaction. Show the Diels–Alder
adduct and propose a mechanism that accounts for the final products.

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