Textbook: Loudon 5th Ed. (2009)

Chapter 16: The Chemistry of Benzene and Its Derivatives

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 587

Use curved arrows to draw a mechanism for the generic electrophilic aromatic substitution (EAS) reaction below.

Problem # 596

Indicate the eletrophile formed by each set of reagents/conditions below.

Problem # 678

Draw the structure of the major organic product from each reaction sequence.

Problem # 588

Let's draw resonance forms to see why some groups are EDG or EWG. (I've started you off)

Where are the positive or negative charges placed in EDG/EWG? (ortho/meta/para) Why would this affect EAS reactions?

Note: EDG = electron donating group, EWG = electron withdrawing group

Problem # 595
 

Phenol can be prepared from benzene and hydrogen peroxide in the presence of a really strong acid. Propose a mechanism for this reaction.

Problem # 722

Show how to prepare vinyl benzene from benzene.

Problem # 589

 -OR is an EDG and an ortho-para director. Let's draw an EAS reaction's cyclohexadienyl cation intermediates to demonstrate why this is true. I've started you off.

What's good about ortho/para? What's bad about meta?

Problem # 590

-NO2 is an EWG and a meta director. Let's draw an EAS reaction's cyclohexadienyl cation intermediates to demonstrate why this is true. I've started you off.

What's good about meta? What's bad about ortho/para?

Problem # 592

Naphthalene undergoes eletrophilic substitution at C-1.

Why is this the case, even though substitution at C-2 gives more resonance forms?

Problem # 594
 

A chemist tried to prepare compound A from benzene via Friedel-Crafts alkylation and instead produced compound B.

Why did this happen? How could the chemist prepare compound A?