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Chapter 18: 21 P (page 702)

Which of the following compounds undergo Friedel–Crafts alkylation with CH3Cland AlCl3? Draw the products formed when a reaction occurs.

Short Answer

Expert verified

Friedel-Craft alkylation substitutes the alkyl group at the ortho and para positions of the substrate having an electron-donating group.

Step by step solution

01

Friedel-Craft reaction

Friedel-Craft alkylation substitutes the alkyl group at the ortho and para positions of the substrate having an electron-donating group.

02

Effect of substituents

Friedel-Crafts reactions do not occur in the presence of strongly deactivating substituents such as NO2,NH2 ,NR2 , NHR groups.

03

Explanation

a. The SO3Hcompound is highly deactivating. Therefore, Friedel-Craft alkylation does not occur.


b. The Cl compound is also electron-donating. Therefore, Friedel-Craft alkylation gives ortho and para products.


c. The NCH32compound is also highly deactivating. Therefore, Friedel-Craft alkylation does not occur.


d. The NHCOCH3 compound is electron-withdrawing, but the ring is sufficient for Friedel-Craft alkylation. Therefore, Friedel-Craft alkylation gives ortho and para products.


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Most popular questions from this chapter

For each N-substituted benzene, predict whether the compound reacts faster than, slower than, or at a similar rate to benzene in electrophilic aromatic substitution. Then draw the major product (s) formed when each compound reacts with a general electrophile E+.

Why is benzene less reactive toward electrophiles than an alkene, even though it has more π electrons than an alkene (six versus two)?

What product is formed when benzene is treated with each organic halide in the presence of AlCl3.

Draw the products of each reaction.

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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