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Orientation Effects of Ring Substituents

Arrange the following compounds in order of increasing rate of reaction with bromine and FeBr.  [Pg.430]

Ethylbenzene contains an aJkyl substituent and is slightly more reactive than benzene. Methyl benzoate has a carbonyl carbon atom bonded to the aromatic ring. As a result, its rate of bromination is significantly slower than that of benzene. Ethoxybenzene has an oxygen atom attached directly to the ring, which causes a significant rate increase over that of benzene. Thus, the order of reactivity for the bromination of benzene in an electrophilic aromatic substitution reaction is methyl benzoate ethylbenzene ethoxybenzene. [Pg.431]

Predict the structure of the product(s) formed in the bromination of each of the following compounds. [Pg.431]

Propiophenone has a carbonyl group bonded to the benzene ring that directs the bromine to the meta position. 7V-methylaniline resembles aniline, and the bromine will be directed to the ortho and para positions. The third compound has two nitro groups. Each one directs the electrophile onto the ring in positions meta to itself. Thus, both groups direct the bromine into the same position. The product [Pg.431]


See other pages where Orientation Effects of Ring Substituents is mentioned: [Pg.322]    [Pg.322]    [Pg.430]   


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Effect of ring substituents

Effect of substituent

Effects of Rings

Effects of substituents

Orientation effect

Orientation, substituent effects

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Ring effect

Ring substituents

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