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Chapter 25: 62 (page 1045)

Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

The cyclic amine reacts with a molecule of formaldehyde to undergo nucleophilic addition.

Nucleophilic addition

Step by step solution

01

Nucleophilic addition

The cyclic amine reacts with a molecule of formaldehyde to undergo nucleophilic addition.

Nucleophilic addition

02

Intramolecular proton transfer (IMPT)

The cation stabilizes via intramolecular proton transfer.

Intramolecular proton transfer

03

Dehydration

The lone pair of electrons on the oxygen atom of the hydroxyl group abstracts a proton followed by dehydration and ring closure.

Dehydration reaction

04

Resonance

The lone pair of electrons on the nitrogen atom delocalizes, which gives the corresponding resonating hybrids.

Resonance forms

Formation of product

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Most popular questions from this chapter

Question: Draw the product of each reaction.

a.

b.

Question: Which amines cannot be prepared by a Gabriel synthesis? Explain your choices.

a.

b.

c.

d.

Question: Draw the product of each reaction.

a.

b.

c.

d.

Question: Draw the product formed by treating each compound with excess CH3I , followed by Ag2O, and then heat.

a.

b.

c.

Question: Write out steps to show how each of the following pairs of compounds can be separated by an extraction procedure.

a.

and

b.

and

See all solutions

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