Textbook: Loudon 5th Ed. (2009)

Chapter 18: The Chemistry of Aryl Halides, Vinylic Halides, and Phenols. Transition-Metal Catalysis

Practice Problems (No matching mendel sets were found.)

Individual Problems

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 # 616

Let's go through another way to make benzyne.

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