Chapter 12: Q16E (page 354)
How would you prepare the following substances, starting from any
compounds having four carbons or fewer?

Short Answer

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Chapter 12: Q16E (page 354)
How would you prepare the following substances, starting from any
compounds having four carbons or fewer?


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The following carboxylic acid can't be prepared from an alkyl halide by either the nitrile hydrolysis route or the Grignard carboxylation route.Explain.

Although the Diels–Alder reaction generally occurs between an electron rich diene and an electron-deficient dienophile, it is also possible to
have inverse-demand Diels–Alder reactions between suitable electrondeficient
conjugated double bonds and electron-rich alkenes. These reactions are particularly useful because they allow for the incorporation of heteroatoms into the new six-membered ring. Predict the products of each inverse-demand Diels–Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one region isomer is possible, draw both.
(a)

(b)

(c)

Identify the functional groups in each of the following molecules:
(a) Methionine, an amino acid:

(b)Ibuprofen, a pain reliever:

(c) Capsaicin, the pungent substance in chili peppers:

Amino acids can be prepared by reaction of alkyl halides with diethyl acetamidomalonate, followed by heating the initial alkylation product with aqueous HCl. Show how you would prepare alanine, , one of the twenty amino acids found in proteins, and propose a mechanism for acid-catalyzed conversion of the initial alkylation product to the amino acid.

As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich Wohler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone.
(a) What is a likely structure for the keto acid?
(b) What is a likely structure for ecgonine, neglecting stereochemistry?
(c) What is a likely structure for cocaine, neglecting stereochemistry?
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