1. one difference between friedel-crafts alkylation and acylation is that a stoi

Question

1. one difference between friedel-crafts alkylation and acylation is that a stoichiometric mount of AlCl3 is required for the acylation reaction. Explain

5. predict the reaction product for the Clemmensen reduction of 4-acetylbiphenyl. this product can also be made through direct Friedel-Crafts alkylation of biphenyl with ethyl bromide and AlCl3. Discuss disadvantages of the alkylation method.

6. predict the expected product of acetylation of 4-bromobiphenyl.

7. predict the structure of the major diacetylated product expected from biphenyl.

8. why does benzoylation not occur twice on the same ring of ferrocene?

9. account for the fact that ferrocene is eluted by the nonpolar solvent, petroleum ether, during column chromatography

10. what feature of the benzoylation of ferrocene makes it particularly attractive for a column chromatography experiment?

Explanation / Answer

1) Eectrophilic aromatic substitution is the responsible for the synthesis of monoacylated products. These monoacylated products are formed from arenes and acyl chlorides or anhydrides.

These products are deactivated, and does not undergo a second substitution reaction, Since the substrate and the products forms complexes, a stoichiometric amount of Lewis acid catalyst is required.

The Friedel-Crafts Alkylation may give polyalkylated products, so the Friedel-Crafts Acylation is a valuable alternative. The acylated products may easily be converted to the corresponding alkanes via Clemmensen Reduction or Wolff-Kishner Reduction

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