Connect Access Card Two Year for Organic Chemistry
Connect Access Card Two Year for Organic Chemistry
10th Edition
ISBN: 9781259636868
Author: Francis Carey
Publisher: McGraw-Hill Education
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Chapter 23, Problem 23P
Interpretation Introduction

Interpretation:

A reasonable synthesis of 3-pentadecyclcatechol from 2,3-dimethoxybenzaldehyde and any necessary organic or inorganic reagentsis to be shown.

Concept introduction:

Ethers react with hydrogen halides to form alcohols and alkyl halide.

Wilkinson catalyst is a coordination complex of rhodium. It is used to reduce double bonds.

In the Wittig reaction, an aldehyde or a ketone reacts with triphenyl phophonium ylide to generate an alkene and triphenylphosphine oxide.

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Doxaprost, an orally active bronchodilator patterned after the natural prostaglandins , is synthesized in the following series of reactions starting with ethyl 2-oxocyclopentanecarboxylate. Except for the Nef reaction in Step 8, we have seen examples of all other types of reactions involved in this synthesis. Q. Write equations to show that Step 6 can be brought about using either methanol or diazomethane (CH2N2) as a source of the -CH3 in the methyl ester.
Doxaprost, an orally active bronchodilator patterned after the natural prostaglandins , is synthesized in the following series of reactions starting with ethyl 2-oxocyclopentanecarboxylate. Except for the Nef reaction in Step 8, we have seen examples of all other types of reactions involved in this synthesis. Q. Step 9 is done by a Wittig reaction. Suggest a structural formula for a Wittig reagent that gives the product shown
Doxaprost, an orally active bronchodilator patterned after the natural prostaglandins , is synthesized in the following series of reactions starting with ethyl 2-oxocyclopentanecarboxylate. Except for the Nef reaction in Step 8, we have seen examples of all other types of reactions involved in this synthesis. Q. Propose a set of experimental conditions to bring about the alkylation in Step 1. Account for the regioselectivity of the alkylation (i.e., that it takes place on the carbon between the two carbonyl groups rather than on the other side of the ketone carbonyl).
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