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Chapter 18: 21 P (page 702)

Which of the following compounds undergo Friedel鈥揅rafts 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

Question: Using resonance structures, explain why a nitroso group (-NO) is an ortho, para director that deactivates a benzene ring toward electrophilic attack.

Draw the products formed when phenol ( C6H5OH) is treated with each set of reagents.

a. [1] HNO3, H2SO4; [2] Sn, HCl

b. [1] CH3CH22COCl,AlCl3; [2] Zn(Hg), HCl

c. [1] CH3CH2Cl,AlCl3; [2]Br2,h谓

d. [1] CH32CHCl,AlCl3; [2] KMnO4

Question: The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown.

a. Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole.

b. Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline.

c. Explain why electrophilic substitution occurs more readily at C3 rather than C2 of indole.

You have learned two ways to make an alkyl benzene: Friedel鈥揅rafts alkylation, and Friedel鈥揅rafts acylation followed by reduction. Although some alkyl benzenes can be prepared by both methods, it is often true that only one method can be used to prepare a given alkyl benzene. Which method(s) can be used to prepare each of the following compounds from benzene? Show the steps that would be used.

Classify each substituent as electron donating or electron withdrawing.
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