What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
d. cyclohexylamine
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1
Identify the structure of the target amine, which is cyclohexylamine, with the formula C6H11NH2.
Understand that in Gabriel synthesis, the phthalimide ion is used to substitute a halide in an alkyl halide to form an N-alkylphthalimide intermediate.
Recognize that the alkyl bromide needed should have the same carbon skeleton as the target amine, minus the amine group.
Determine that the alkyl group in cyclohexylamine is cyclohexyl, which means the corresponding alkyl bromide should be cyclohexyl bromide.
Conclude that cyclohexyl bromide is the appropriate alkyl bromide to use in the Gabriel synthesis to prepare cyclohexylamine.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Gabriel Synthesis
Gabriel synthesis is a method used to prepare primary amines from alkyl halides. It involves the use of phthalimide, which reacts with a base to form a phthalimide salt. This salt then undergoes nucleophilic substitution with an alkyl halide, leading to the formation of the desired amine after hydrolysis. This method is particularly useful for avoiding the formation of secondary and tertiary amines.
Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (such as bromine, chlorine, or iodine). In the context of Gabriel synthesis, the choice of alkyl halide is crucial, as it determines the structure of the resulting amine. For cyclohexylamine, an appropriate alkyl bromide would be cyclohexyl bromide, which provides the necessary carbon framework for the amine.
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In Gabriel synthesis, the nucleophile is the phthalimide salt, and the electrophile is the alkyl halide. Understanding this mechanism is essential for predicting the outcome of the reaction and ensuring the correct amine is synthesized.