A mechanism for the reaction of benzene with 2,2,5,5-teteamethyltetrahydrofuran shown below is to be proposed. Concept introduction: The reaction involves the electrophilc substitution of cyclic ether into a benzene ring. The electrophile can be produced by the protonation of the ethereal oxygen followed by a cleavage of a C-O bond. The eletrophilic attack will lead to the formation of an alcohol. Protonation of the alcohol and subsequent elimination of water generates another carbocation which can internally attack the ring. The loss of a proton from the intermediate will lead to product expected. To propose: A mechanism for the reaction of benzene with 2,2,5,5-teteamethyltetrahydrofuran shown.

Question

Synthesis of Ibuprofen-Part 2: 1. Some pain relievers including ibuprofen (MotrinⓇ) and naproxen (Aleve®) are "α-arylpropanoic acids." Look up the structure of naproxen (AleveⓇ), another a-arylpropionic acid. Using the same reactions that we used for making ibuprofen, show how to make naproxen from the compound below. Show all intermediates and reagents in your synthesis. Show how you would prepare ibuprofen starting from p-isobutylbenzene rather than p-isobutylacetophenenone. What reaction steps would need to change/add? 3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?

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Question

Chapter 16.SE, Problem 70AP

Interpretation Introduction

Interpretation:

A mechanism for the reaction of benzene with 2,2,5,5-teteamethyltetrahydrofuran shown below is to be proposed.

Concept introduction:

The reaction involves the electrophilc substitution of cyclic ether into a benzene ring. The electrophile can be produced by the protonation of the ethereal oxygen followed by a cleavage of a C-O bond. The eletrophilic attack will lead to the formation of an alcohol. Protonation of the alcohol and subsequent elimination of water generates another carbocation which can internally attack the ring. The loss of a proton from the intermediate will lead to product expected.

To propose:

A mechanism for the reaction of benzene with 2,2,5,5-teteamethyltetrahydrofuran shown.

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Synthesis of Ibuprofen-Part 2: 1. Some pain relievers including ibuprofen (MotrinⓇ) and naproxen (Aleve®) are "α-arylpropanoic acids." Look up the structure of naproxen (AleveⓇ), another a-arylpropionic acid. Using the same reactions that we used for making ibuprofen, show how to make naproxen from the compound below. Show all intermediates and reagents in your synthesis. Show how you would prepare ibuprofen starting from p-isobutylbenzene rather than p-isobutylacetophenenone. What reaction steps would need to change/add? 3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?

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