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Ch. 19 - Amines
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 19 - AminesProblem 42c
Chapter 19, Problem 42c

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

Verified step by step guidance
1
Step 1: Begin with the starting material, piperidine (a cyclic secondary amine). The goal is to methylate the nitrogen atom and introduce a double bond in the ring structure.
Step 2: Use methyl iodide (CH3I) or dimethyl sulfate as a methylating agent to add two methyl groups to the nitrogen atom. This reaction typically occurs via nucleophilic substitution, where the lone pair on the nitrogen attacks the methylating agent.
Step 3: To introduce the double bond in the ring, perform a dehydrogenation reaction. This can be achieved using a strong base such as potassium tert-butoxide (KOtBu) or sodium hydride (NaH) to abstract a proton, leading to the formation of the double bond.
Step 4: Ensure the reaction conditions are controlled to avoid overreaction or side reactions. For example, use an appropriate solvent like tetrahydrofuran (THF) or dimethylformamide (DMF) to facilitate the reaction.
Step 5: Purify the product using techniques such as distillation or chromatography to isolate the desired compound, N,N-dimethyl-2,3-dihydropyrrole.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Hofmann Elimination

Hofmann elimination is a chemical reaction that involves the conversion of primary amines to alkenes through the formation of an N-chloroamine intermediate. This process typically requires the use of reagents such as chlorine or bromine in the presence of a base, leading to the elimination of an amine and the formation of an alkene. Understanding this mechanism is crucial for synthesizing specific alkenes from amines.
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Reagents and Conditions

The choice of reagents and reaction conditions is vital in organic synthesis. In Hofmann elimination, reagents like sodium hypochlorite or bromine are commonly used to generate the N-chloroamine, while a strong base, such as sodium hydroxide, facilitates the elimination step. Recognizing the appropriate reagents and their roles helps in successfully executing the synthesis.
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Mechanism of Elimination Reactions

Elimination reactions involve the removal of atoms or groups from a molecule, resulting in the formation of a double bond. In the context of Hofmann elimination, the mechanism includes the formation of a cyclic intermediate followed by the loss of a leaving group and a proton, leading to the creation of an alkene. A solid grasp of elimination mechanisms is essential for predicting the products of such reactions.
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Related Practice
Textbook Question

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

(a)

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Textbook Question

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

(b)

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Textbook Question

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

(g)

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Textbook Question

The mass spectrum of tert-butylamine follows shows an intense base peak at m/z 58, and very little else. Use a diagram to show the cleavage that accounts for the base peak. Suggest why no molecular ion is visible in this spectrum.

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Textbook Question

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

(e)

(f)

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Textbook Question

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

(d)

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