(a)
Interpretation: Using a Gabriel synthesis, a give set of primary amine compounds have to be synthesized.
Concept Introduction: The general formula for primary amine is –NH2. There are several methods available to prepare primary
Step-1: Formation of potassium phthalimide (deprotonation)
Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.
Step-2: Formation of R−N bond by SN2 nucleophilic substitution
The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary
Step-3: Formation of primary amine by hydrolysis
The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.
(b)
Interpretation: Using a Gabriel synthesis, a give set of primary amine compounds have to be synthesized.
Concept Introduction: The general formula for primary amine is –NH2. There are several methods available to prepare primary amines. Among them, Gabriel synthesis plays a very important role for preparing it. In this method, secondary and tertiary amines are not formed as side products. It involves in three steps.
Step-1: Formation of potassium phthalimide (deprotonation)
Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.
Step-2: Formation of R−N bond by SN2 nucleophilic substitution
The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary alkyl halides (R−X), R and X get positive and negative charges, respectively when they ionize. As a result, a bond between nitrogen of phthalimide and carbon of R is formed. This is SN2 nucleophilic substitution reaction. Halogen atom is going away as halide anion.
Step-3: Formation of primary amine by hydrolysis
The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.
(c)
Interpretation: Using a Gabriel synthesis, a give set of primary amine compounds have to be synthesized.
Concept Introduction: The general formula for primary amine is –NH2. There are several methods available to prepare primary amines. Among them, Gabriel synthesis plays a very important role for preparing it. In this method, secondary and tertiary amines are not formed as side products. It involves in three steps.
Step-1: Formation of potassium phthalimide (deprotonation)
Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.
Step-2: Formation of R−N bond by SN2 nucleophilic substitution
The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary alkyl halides (R−X), R and X get positive and negative charges, respectively when they ionize. As a result, a bond between nitrogen of phthalimide and carbon of R is formed. This is SN2 nucleophilic substitution reaction. Halogen atom is going away as halide anion.
Step-3: Formation of primary amine by hydrolysis
The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.
(d)
Interpretation: Using a Gabriel synthesis, a give set of primary amine compounds have to be synthesized.
Concept Introduction: The general formula for primary amine is –NH2. There are several methods available to prepare primary amines. Among them, Gabriel synthesis plays a very important role for preparing it. In this method, secondary and tertiary amines are not formed as side products. It involves in three steps.
Step-1: Formation of potassium phthalimide (deprotonation)
Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.
Step-2: Formation of R−N bond by SN2 nucleophilic substitution
The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary alkyl halides (R−X), R and X get positive and negative charges, respectively when they ionize. As a result, a bond between nitrogen of phthalimide and carbon of R is formed. This is SN2 nucleophilic substitution reaction. Halogen atom is going away as halide anion.
Step-3: Formation of primary amine by hydrolysis
The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.
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Chapter 23 Solutions
Student Study Guide and Solutions Manual T/A Organic Chemistry
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