Textbook: Wade 7th Ed. (2009)

Chapter 17: Reactions of Aromatic Compounds

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 580

Draw all resonance forms for each species.

For the anion and cation species, used curved arrows. For the radical species, use hooks.

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 # 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 # 611

Draw in the arrows to show the electron flow and resonance forms in the nucleophilic aromatic substitution reaction below.

Note: Depending on the textbook, nucleophilic aromatic substitution is referred to as NAS, SNAr, or addition-elimination.


Problem # 612

Draw a mechanism for the nucleophilic aromatic substitution (SNAr) reaction below. Show all resonance forms of the intermediate.

Problem # 615

Let's go through a benzyne reaction (also called elimination-addition).

In the reaction below, the strong base (NaNH2) will form a benzyne intermediate, which when forms either ortho nitroaniline or meta nitroaniline.

Used curved arrows to show the formation of each intermediate and the final products.

Problem # 305

Rank each group of acids in order of decreasing acidity. (1 = most acidic)

Explain your reasoning. You will have to use more than one rule in your explanation (resonance, electronegativity, atomic radius, etc.). 


Problem # 581

Draw all products for the two reactions below.

The allylic alkene gives two products- the 1,2 product, and the 1,4 product. 

However, the benzylic alkene only gives the one product (analogous to the 1,2 product), instead of multiple products (like the 1,4 product, 1,6 product, and 1,8 product). Why is this the case?

Problem # 1281

Allylic and benzylic halides tend to undergo both SN1 and SN2 substitution reactions at a faster rate than their alkyl counterparts.

For example, both allyl chloride and benzyl chloride undergo SN2 reaction at a faster rate than propyl chloride. 

The same holds true for SN1 reactions: a 2° allyl or benzyl halide undergoes SN1 reaction faster than a 2° alkyl halide. Explain.

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 # 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 # 616

Let's go through another way to make benzyne.

First, let's form a Grignard reagent. Then, let's elminate to form benzyne.

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?

Problem # 592

Naphthalene undergoes eletrophilic substitution at C-1.

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