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Suggest two other compounds that might be used in place of tert.-butyl alcohol to form l,4-di-tert.-butyl-2,5-dimethoxybenzene

Suggest two other compounds that might be used in place of tert.-butyl alcohol to form l,4-di-tert.-butyl-2,5-dimethoxybenzene

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Experiment: Friedel-Crafts Alkylation

Question: Suggest two other compounds that might be used in place of tert.-butyl alcohol to form l,4-di-tert.-butyl-2,5-dimethoxybenzene

materials used:

  • 1.15 g of 1,4-dimethoxybenzene

  • 2.2 mL of tert.-butyl alcohol

  • 3.4 mL glacial acetic acid

  • 4.50 mL of concentrated sulfuric acid

Product characterization:

    • 0.77 g of the final product
In the current experiment, we will use a different electrophile (the tert-butyl cation) to alkylate 1,4-dimethoxybenzene. This is a Friedel-Crafts Alkylation reaction. **Diagram Explanation:** The diagram illustrates a chemical reaction where 1,4-dimethoxybenzene undergoes a Friedel-Crafts Alkylation. - **Reactant Side (Left):** - A benzene ring with two methoxy groups (OCH₃) attached. - The benzene ring is labeled with "H₃CO" and "OCH₃." - **Reaction Conditions:** - The presence of (CH₃)₃COH (tert-butyl alcohol) is indicated. - Acid catalysts are shown: CH₃COOH (acetic acid) and H₂SO₄ (sulfuric acid). - **Product Side (Right):** - The resulting compound is a benzene ring with the original methoxy groups and two tert-butyl groups ((H₃C)₃C) attached. - The attachment of the tert-butyl groups results in the substitution pattern shown as C(CH₃)₃ on the ring. This reaction demonstrates the electrophilic aromatic substitution mechanism typical of Friedel-Crafts Alkylation, where the aromatic ring is alkylated by the introduction of a tert-butyl group.
Transcribed Image Text:In the current experiment, we will use a different electrophile (the tert-butyl cation) to alkylate 1,4-dimethoxybenzene. This is a Friedel-Crafts Alkylation reaction. **Diagram Explanation:** The diagram illustrates a chemical reaction where 1,4-dimethoxybenzene undergoes a Friedel-Crafts Alkylation. - **Reactant Side (Left):** - A benzene ring with two methoxy groups (OCH₃) attached. - The benzene ring is labeled with "H₃CO" and "OCH₃." - **Reaction Conditions:** - The presence of (CH₃)₃COH (tert-butyl alcohol) is indicated. - Acid catalysts are shown: CH₃COOH (acetic acid) and H₂SO₄ (sulfuric acid). - **Product Side (Right):** - The resulting compound is a benzene ring with the original methoxy groups and two tert-butyl groups ((H₃C)₃C) attached. - The attachment of the tert-butyl groups results in the substitution pattern shown as C(CH₃)₃ on the ring. This reaction demonstrates the electrophilic aromatic substitution mechanism typical of Friedel-Crafts Alkylation, where the aromatic ring is alkylated by the introduction of a tert-butyl group.
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