Predict the product(s) of the reactions shown.
(i)

Guida verificata passo dopo passo

Step 1: Identify the starting material as phthalimide, which is a cyclic imide derived from phthalic acid.

Step 2: Recognize the first reagent, nBuBr (n-butyl bromide), which is an alkyl halide. This suggests an alkylation reaction where the nitrogen atom of the phthalimide will act as a nucleophile.

Step 3: Understand that the phthalimide nitrogen will attack the n-butyl bromide, displacing the bromide ion and forming N-butylphthalimide.

Step 4: Note the second step involves KOH and hydrazine (H2NNH2) under heat (Δ). This indicates a Gabriel synthesis, where the phthalimide is converted to a primary amine.

Step 5: In the Gabriel synthesis, hydrazine reacts with N-butylphthalimide to release the primary amine, n-butylamine, and form phthalhydrazide as a byproduct.

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Nucleophilic Substitution Reaction

Nucleophilic substitution is a fundamental class of reactions in organic chemistry where a nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms to replace a leaving group. In the given reaction, nBuBr (n-butyl bromide) acts as the alkylating agent, where the bromide ion is the leaving group, and the nitrogen atom in the imide acts as the nucleophile.

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Nucleophiles and Electrophiles can react in Substitution Reactions.

Gabriel Synthesis

Gabriel synthesis is a method used to synthesize primary amines from primary alkyl halides. The reaction involves the use of phthalimide, which is deprotonated to form a nucleophilic phthalimide anion that reacts with an alkyl halide. In this reaction, the phthalimide is alkylated by nBuBr, and subsequent hydrazinolysis releases the primary amine, n-butylamine.

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General Reaction

Hydrazinolysis

Hydrazinolysis is a chemical reaction where hydrazine is used to cleave a bond, often in the context of removing protecting groups. In the Gabriel synthesis, hydrazinolysis is used to convert the N-alkylphthalimide intermediate into the corresponding primary amine. Here, hydrazine reacts with the alkylated phthalimide to release n-butylamine and phthalhydrazide as a byproduct.

Pratica correlata

Domanda del libro di testo

The Gabriel synthesis is most frequently done with 1° alkyl halides. Why is it less successful with more substituted halides?

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Domanda del libro di testo

Suggest reagents to carry out the following transformations. Some may require more than one step.

(b)

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Domanda del libro di testo

Predict the product(s) of the reactions shown.