Chapter 16 Multiple Choice Questions

. Which is most reactive in electrophilic substitution?

. Which is least reactive in electrophilic substitution?

. Which gives a meta nitro compound as the main product upon nitration with a nitric acid-sulfuric acid mixture?

. Which is most reactive in electrophilic substitution?

. Which is least reactive in electrophilic substitution?

. Which gives a meta nitro compound as the main product upon nitration with a nitric acid-sulfuric acid mixture?

. Which will be the main product upon chlorination of m-nitrotoluene with Cl₂/AlCl₃?

. Which is obtained as the main mononitration product upon reaction of m-t-butylanisole (1-t-butyl-3-methoxybenzene) with HNO₃-H₂SO₄?

. Which of the following statements regarding Friedel-Crafts reactions is wrong?

Alkylation of benzene with an alkyl chloride requires only a catalytic amount of a Lewis acid such as aluminum chloride.

Alkylation of benzene with an alcohol requires only a catalytic amount of a Brønsted acid such as phosphoric acid.

Acetylation of benzene with acetyl chloride requires only a catalytic amount of a Lewis acid.

Acetylation of benzene with acetic anhydride requires more than one equivalent of a Lewis acid.

. Which of the following statements regarding electrophilic aromatic substitution is wrong?

Acetyl and cyano substituents are both deactivating and m-directing.

Alkyl groups are activating and o,p-directing.

Ammonio groups are m-directing but amino groups are and o,p-directing.

Chloro and methoxy substituents are both deactivating and o,p-directing.

. Which is most reactive in electrophilic substitution?

. Which is least reactive in electrophilic substitution?

. Which gives a para nitro compound as the main product upon nitration with a nitric acid-sulfuric acid mixture?

. Which gives a meta nitro compound as the main product upon nitration with a nitric acid-sulfuric acid mixture?

. Which of (a)-(d) does not give isopropylbenzene as a product upon reaction with benzene?

(CH₃)₂CHCl/AlCl₃

CH₃CH₂CH₂Cl/AlCl₃

CH₃CH=CH₂/H₃PO₄

(CH₃)₂C=CH₂/H₃PO₄

. Which combination of reagents used in the indicated order with benzene will give m-nitropropylbenzene?

1) HNO₃/H₂SO₄, 2) CH₃CH₂CH₂Cl/AlCl₃

1) CH₃CH₂CH₂Cl/AlCl₃, 2) HNO₃/H₂SO₄

1) CH₃CH₂COCl/AlCl₃, 2) HNO₃/H₂SO₄, 3) H₂NNH₂/NaOH

1) HNO₃/H₂SO₄, 2) CH₃CH₂COCl/AlCl₃, 3) H₂NNH₂/NaOH

. Which pair of compounds are the most probable main products of the following reaction?

. Which will be the main product upon bromination of phenyl benzoate with Br₂/AlBr₃?

. Which of the following statements regarding electrophilic aromatic substitution is wrong?

Sulfonation of toluene is reversible.

Friedel-Crafts alkylation of benzene can be reversible.

Friedel-Crafts alkylation with primary alkyl chloride may involve rearrangement.

Friedel-Crafts acylation of nitrobenzene readily gives a meta substitution product.

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