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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

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

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

Draw the products formed when each amine is treated with [1] CH3I(excess); [2] Ag2O; [3] 鈭�. Indicate the major product when a mixture results.

a

b

c

d

Question: a. Explain why phentermine phCH2CCH32NH2 can't be made by a reductive amination reaction.

b. Give a systematic name for phentermine, one of the components of the banned diet drug fen鈥損hen.

Draw a stepwise mechanism for each reaction.
See all solutions

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