26. Amines

The following reaction takes place several times faster than the reaction of 2-chlorobutane with HO^-:

b. Explain why the OH group in the product is not bonded to the carbon that was bonded to the Cl group in the reactant.

Describe a synthesis for each of the following compounds, using the given starting material and any necessary reagents:

b.

What are the minor products of the preceding Hofmann elimination reaction?

What are the major products of the following reaction?

What is the major product of each of the following reactions?

b .

When piperidine undergoes the series of reactions shown here, 1,4-pentadiene is obtained as the product. When the four different methyl-substituted piperidines undergo the same series of reactions, each forms a different diene: 1,5-hexadiene; 1,4-pentadiene; 2-methyl-1,4-pentadiene; and 3-methyl-1,4-pentadiene. Which methyl-substituted piperidine forms which diene?

The following reaction takes place several times faster than the reaction of 2-chlorobutane with HO^-:

a. Explain the enhanced reaction rate.

Using any necessary reagents, show how you would accomplish the following syntheses.

(c)

Predict the products of the following reactions:

(j)

Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag₂O, and heating.

(e)

Predict the products of the following reactions:

(e)

(f)

Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag₂O, and heating.

(a) hexan-2-amine

(b) 2-methylpiperidine

(c) N-ethylpiperidine

When the (R,R) isomer of the amine shown is treated with an excess of methyl iodide, then silver oxide, then heated, the major product is the Hofmann product.

(a) Draw the structure of the major (Hofmann) product.