
(a)
Interpretation: Hexylamines have to be synthesized from various starting compounds.
Concept Introduction: The general formula for hexylamine is C6H13NH2. 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: Hexylamines have to be synthesized from various starting compounds.
Concept Introduction: The general formula for hexylamine is C6H13NH2. 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: Hexylamines have to be synthesized from various starting compounds.
Concept Introduction: The general formula for hexylamine is C6H13NH2. 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: Hexylamines have to be synthesized from various starting compounds.
Concept Introduction: The general formula for hexylamine is C6H13NH2. 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.

Want to see the full answer?
Check out a sample textbook solution
Chapter 22 Solutions
EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
- Would the following organic synthesis occur in one step? Add any missing products, required catalysts, inorganic reagents, and other important conditions. Please include a detailed explanation and drawings showing how the reaction may occur in one step.arrow_forward(a) Sketch the 'H NMR of the following chemical including the approximate chemical shifts, the multiplicity (splitting) of all signals and the integration (b) How many signals would you expect in the 13C NMR? CH3arrow_forwardDraw the Show the major and minor product(s) for the following reaction mechanisms for both reactions and show all resonance structures for any Explain why the major product is favoured? intermediates H-Brarrow_forward
- 3. Draw ALL THE POSSBILE PRODUCTS AND THE MECHANISMS WITH ALL RESONANCE STRUCTURES. Explain using the resonance structures why the major product(s) are formed over the minor product(s). H₂SO4, HONO CHarrow_forward7. Provide the product(s), starting material(s) and/or condition(s) required for the No mechanisms required. below reaction HO + H-I CI FO Br2, FeBr3 O I-Oarrow_forward6. Design the most efficient synthesis of the following product starting from phenot Provide the reaction conditions for each step (more than one step is required) and explain the selectivity of each reaction. NO MECHANISMS ARE REQUIRED. OH step(s) CIarrow_forward
- What is the skeletal structure of the product of the following organic reaction?arrow_forwardIf a reaction occurs, what would be the major products? Please include a detailed explanation as well as a drawing showing how the reaction occurs and what the final product is.arrow_forwardWhat is the major organic product of the following nucleophilic acyl substitution reaction of an acid chloride below?arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





