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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 structure that corresponds to each name.

  1. N-isobutylcyclopentanamine
  2. tri-tert-butylamine
  3. N, N-diisopropylaniline
  4. N-methyl pyrrole
  5. N-methylcyclopentanamine
  6. 3-methylhexan-2-amine
  7. 2-sec-butylpiperidine
  8. (S)-heptan-2-amine

Question: Draw the products of each acid–base reaction. Indicate whether equilibrium favors the reactants or products.

a.

b.

c.

Question: What is the structure of an unknown compound with molecular formula C6H15N that gives the following 1H NMR absorptions: 0.9 (singlet, 1 H), 1.10 (triplet, 3 H), 1.15 (singlet, 9 H), and 2.6 (quartet, 2 H) ppm?

Question: Give a systematic or common name for each compound.

a.

b.

c.

d.

e.

f.

g.

h.

Draw the organic products formed in each reaction.

a

b

c

d

e

f

g

h

i

j
See all solutions

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