(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.
Want to see the full answer?
Check out a sample textbook solution
Chapter 22 Solutions
ORGANIC CHEMISTRY, WITH SOL. MAN/ STUDY
- 4. Read paragraph 4.15 from your textbook, use your calculated lattice energy values for CuO, CuCO3 and Cu(OH)2 an explain thermal decomposition reaction of malachite: Cu2CO3(OH)2 →2CuO + H2O + CO2 (3 points)arrow_forwardPlease sirrr soollveee these parts pleaseeee and thank youuuuuarrow_forwardIII O Organic Chemistry Using wedges and dashes in skeletal structures Draw a skeletal ("line") structure for each of the molecules below. Be sure your structures show the important difference between the molecules. key O O O O O CHON Cl jiii iiiiiiii You can drag the slider to rotate the molecules. Explanation Check Click and drag to start drawing a structure. Q Search X G ©2025 McGraw Hill LLC. All Rights Reserved. Terms of Use F 3 W C 3/5arrow_forward
- 3. Use Kapustinskii's equation and data from Table 4.10 in your textbook to calculate lattice energies of Cu(OH)2 and CuCO3 (4 points)arrow_forward2. Copper (II) oxide crystalizes in monoclinic unit cell (included below; blue spheres 2+ represent Cu²+, red - O²-). Use Kapustinski's equation (4.5) to calculate lattice energy for CuO. You will need some data from Resource section of your textbook (p.901). (4 points) CuOarrow_forwardWhat is the IUPAC name of the following compound? OH (2S, 4R)-4-chloropentan-2-ol O (2R, 4R)-4-chloropentan-2-ol O (2R, 4S)-4-chloropentan-2-ol O(2S, 4S)-4-chloropentan-2-olarrow_forward
- Use the reaction coordinate diagram to answer the below questions. Type your answers into the answer box for each question. (Watch your spelling) Energy A B C D Reaction coordinate E A) Is the reaction step going from D to F endothermic or exothermic? A F G B) Does point D represent a reactant, product, intermediate or transition state? A/ C) Which step (step 1 or step 2) is the rate determining step? Aarrow_forward1. Using radii from Resource section 1 (p.901) and Born-Lande equation, calculate the lattice energy for PbS, which crystallizes in the NaCl structure. Then, use the Born-Haber cycle to obtain the value of lattice energy for PbS. You will need the following data following data: AH Pb(g) = 196 kJ/mol; AHƒ PbS = −98 kJ/mol; electron affinities for S(g)→S¯(g) is -201 kJ/mol; S¯(g) (g) is 640kJ/mol. Ionization energies for Pb are listed in Resource section 2, p.903. Remember that enthalpies of formation are calculated beginning with the elements in their standard states (S8 for sulfur). The formation of S2, AHF: S2 (g) = 535 kJ/mol. Compare the two values, and explain the difference. (8 points)arrow_forwardIn the answer box, type the number of maximum stereoisomers possible for the following compound. A H H COH OH = H C Br H.C OH CHarrow_forward
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles 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 Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY