Furan undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient.For example, furan reacts with bromine to give 2-bromofuran.(a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms ofeach sigma complex, and compare their stabilities.(b) Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.O Br O123furan 2-bromofuran
Organomagnesium compounds
The interaction of alkyl halide with Mg metal in a suitable ether solvent is the common method for the synthesis of the Grignard reagent.
Hydrolysis Grignard Reactions and Reduction
Organomagnesium halides are Grignard reagents. Francois Auguste Victor Grignard, a French chemist who received the Nobel Prize in Chemistry in 1912, created these highly useful reagents.
Furan undergoes electrophilic
For example, furan reacts with bromine to give 2-bromofuran.
(a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms of
each sigma complex, and compare their stabilities.
(b) Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.
O Br O
1
2
3
furan 2-bromofuran
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