Chapter 17: Q30P (page 885)
Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.
Chapter 17: Q30P (page 885)
Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.
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Get started for freeThe bombardier beetle defends itself by spraying a hot quinone solution from its abdomen (see photo). This solution is formed by the enzyme-catalyzed oxidation of hydroquinone by hydrogen peroxide. Write a balanced equation for this oxidation.
When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 °C, an interesting Diels–Alder adduct of the formula C20H14results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and a broad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings of anthracene reacted as a diene.
What substituted alkene would you use in the Heck reaction to make the following products?
Phenolphthalein, a common nonprescription laxative, is also an acid-base indicator that is colorless in acid and red in base. Phenolphthalein is synthesized by the acid-catalyzed reaction of phthalic anhydride with 2 equivalents of phenol.
(a) Propose a mechanism for the synthesis of phenolphthalein.
(b) Propose a mechanism for the conversion of phenolphthalein to its red dianion in the base.
(c) Use resonance structures to show that the two phenolic oxygen atoms are equivalent (each with half a negative charge) in the red phenolphthalein dianion.
Phthalic anhydride Phenolphthalein red dianion
1,4-Benzoquinone is a good Diels–Alder dienophile. Predict the products of its reaction with
(a) buta-1,3-diene
(b) cyclopenta-1,3-diene
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