Exam 19: Amines

Devise an efficient method for preparing cyclohexylamine from cyclohexylmethanol.

The following substrate is a starting material in the synthesis of compounds having opiod activity (J. Med. Chem. 2011, 957). Show all products that would result from the reaction below.

Can 1-hexanamine be prepared in good yield from the reaction of a 1:1 molar ratio of ammonia and 1-bromohexane? Why or why not?

Provide the structure of the major organic product in the reaction below.

Provide the systematic name for the compound below. (CH₃)₄N⁺Cl^-

Circle the stronger base in the pair below, and briefly explain your choice.

Name the compound shown below.

In ¹H NMR protons on the α-carbon of amines typically absorb between θ:

Compound A, C₉H₁₇N, is an optically inactive alkaloid, containing a tertiary amine that is not located at the bridgehead of the structures fused bicyclic ring system. Exhaustive alkylation of A with methyl iodide, followed by a Hofmann elimination reaction resulted in a racemic mixture of chiral tertiary amine products B, C₁₀H₁₉N. Provide a structure for A and one of the enantiomeric products B.

Provide the major organic product of the following reaction.

Provide the structure of the major organic product in the reaction below.

Provide the structure of the major organic product in the reaction below.

Provide the major organic product of the following reaction.

The nitrogen's lone pair in pyrrolidine is best described as occupying what type of orbital?

Which has the higher boiling point, butan-1-ol or 1-butanamine? Explain briefly.

Provide the structure of the major organic product in the reaction below.

Circle the stronger base in the pair below, and briefly explain your choice.

Identify the correct systematic name for the following compound.

Which of the following amines can be resolved into enantiomers?

Devise an efficient method for preparing fluorobenzene from benzene.