Chapter 25: Amines

Question:The pKa of the conjugate acid of guanidine is 13.6, making it one of the strongest neutral organic bases. Offer an explanation.

Question: Rank the following compounds in order of increasing basicity and explain the order you chose.

Rank the following compounds in order of increasing basicity and explain the order you choose.

Question: Draw the product Y of the following reaction sequence. Y was an intermediate in the remarkable synthesis of cyclooctatetraene by Wilstatter in 1911.

Draw the product Y of the following reaction sequence. Y was an intermediate in the remarkable synthesis of cyclooctatetraene by Wilstatter in 1911.

Question: Devise a synthesis of each compound from the given starting material(s). Albuterol is a bronchodilator and proparacaine is a local anesthetic.

Devise a synthesis of each compound from the given starting material(s). Albuterol is a bronchodilator and proparacaine is a local anesthetic.

a.

b.

Question: Heating compound X with aqueous formaldehyde forms Y $\left(C_{17}{H}_{23}NO\right)$,which has been converted to a mixture of lupinine and epilupinine, alkaloids isolated from lupin, a perennial ornamental plant commonly seen on the roadside in parts of Alaska (Section 25.10). Identify Y and explain how it is formed.

Heating compound X with aqueous formaldehyde forms Y $\left({\mathbf{C}}_{\mathbf{17}}{\mathbf{H}}_{\mathbf{23}}\mathbf{N}\mathbf{O}\right)$,which has been converted to a mixture of lupinine and epilupinine, alkaloids isolated from lupin, a perennial ornamental plant commonly seen on the roadside in parts of Alaska (Section 25.10). Identify Y and explain how it is formed.