Textbook: McMurry 8th Ed. (2011)

Chapter 24: Amines and Heterocycles

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 755
 

The nitrosyl cation is shown below. Also shown are several proposed resonance arrows, only one of which is correct.

Draw the resonance forms that would follow from each set of arrows, and include formal charges. Which one is the correct resonance form? Explain your reasoning.

Problem # 753

Rank the amines W through Z below in order of decreasing basicity (1 = most basic). Explain your reasoning.

Problem # 754

Show how each amine can be prepared from a carbonyl and an amine via reductive amination.

Problem # 756

For each amine below, show all Hofmann elmination products.

If more than one product is formed, predict which one will be the major product.

Problem # 591

Pyrrole undergoes eletrophilic aromatic substitution at C-2. Let's compare the resonance forms of EAS carbocation intermediates to see why this is the case. What do you think? Why C-2 and not C-3?

Problem # 584

Imidazole (shown below) has two nitrogen atoms, N-1 and N-3. Which nitrogen is more basic?

To answer this problem, draw the product after each nitrogen protonates, and compare their stabilities. Explain your reasoning.

Problem # 728

The acyl group is a protecting group for amines. Amines can be acylated using acetic anhydride, and deacylated with base.

Propose a mechanism for each reaction.

Problem # 752

Rank the amines A through D below in order of decreasing basicity (1 = most basic). Explain your reasoning.

Problem # 757

Propose a synthesis to accomplish each transformation. The only carbon sources allowed are alkenes and NaCN.

Problem # 593

a) Rationalize the relative stabilities of the cation species below.

 

b) Pyridine undergoes eletrophilic substitution at C-3. Let's compare the resonance forms of EAS carbocation intermediates to see why this is the case. Consider part a) in your explanation.