Other groups besides H+ can act as leaving groups in electrophilic aromatic substitution. One of the best is the trimethylsilyl group, Me3Si-. For example, treatment of Me3SiC6H5 with CF3COOD rapidly forms C6H5D. What properties of a silicon-carbon bond allow you to predict this kind of reactivity?

Other groups besides H+ can act as leaving groups in electrophilic aromatic substitution. One of the best is the trimethylsilyl group, Me3Si-. For example, treatment of Me3SiC6H5 with CF3COOD rapidly forms C6H5D. What properties of a silicon-carbon bond allow you to predict this kind of reactivity?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution

Section16.4: Substituent Effects In Electrophilic Substitutions

Problem 11P

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Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

Other groups besides H⁺ can act as leaving groups in electrophilic aromatic substitution. One of the best is the trimethylsilyl group, Me₃Si-. For example, treatment of
Me₃SiC₆H₅ with CF₃COOD rapidly forms C₆H₅D. What properties of a silicon-carbon bond allow you to predict this kind of reactivity?

Definition Definition Organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Aromatic organic compounds, also called arenes, are an important class of hydrocarbons under the branch of organic chemistry.

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