Chapter 18: 13 P (page 691)
Which substituents have an electron-withdrawing and which have an electron-donating inductive effect
a
b
c
Short Answer
a. Electron-donating group.
b. Electron-withdrawing group.
c. Electron-withdrawing group.
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Chapter 18: 13 P (page 691)
Which substituents have an electron-withdrawing and which have an electron-donating inductive effect
a
b
c
a. Electron-donating group.
b. Electron-withdrawing group.
c. Electron-withdrawing group.
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Question: Draw a stepwise, detailed mechanism for the dienone–phenol rearrangement, a reaction that forms alkyl-substituted phenols from cyclohexadienones.

Draw the products formed when each compound is treated with

Draw a detailed mechanism for the chlorination of benzene using and .
Question: Explain the reactivity and orientation effects observed in each heterocycle.

a. Pyridine is less reactive than benzene in electrophilic aromatic substitution and yields 3-substituted products.
b. Pyrrole is more reactive than benzene in electrophilic aromatic substitution and yields 2-substituted products.
Draw all resonance structures for each compound and use the resonance structures to determine if the substituent has an electron-donating or electron-withdrawing resonance effect.

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