(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.
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Chapter 22 Solutions
EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
- Q1: For each molecule, assign each stereocenter as R or S. Circle the meso compounds. Label each compound as chiral or achiral. + CI Br : Н OH H wo་ཡིག་ཐrow HO 3 D ။။ဂ CI Br H, CI Br Br H₂N OMe R IN I I N S H Br ជ័យ CI CI D OHarrow_forwardPlease correct answer and don't use hand ratingarrow_forwardNonearrow_forward
- %Reflectance 95 90- 85 22 00 89 60 55 50 70 65 75 80 50- 45 40 WA 35 30- 25 20- 4000 3500 Date: Thu Feb 06 17:21:21 2025 (GMT-05:0(UnknownD Scans: 8 Resolution: 2.000 3000 2500 Wavenumbers (cm-1) 100- 2981.77 1734.25 2000 1500 1000 1372.09 1108.01 2359.09 1469.82 1181.94 1145.20 1017.01 958.45 886.97 820.49 668.25 630.05 611.37arrow_forwardNonearrow_forwardCH3 CH H3C CH3 H OH H3C- -OCH2CH3 H3C H -OCH3 For each of the above compounds, do the following: 1. List the wave numbers of all the IR bands in the 1350-4000 cm-1 region. For each one, state what bond or group it represents. 2. Label equivalent sets of protons with lower-case letters. Then, for each 1H NMR signal, give the 8 value, the type of splitting (singlet, doublet etc.), and the number protons it represents. of letter δ value splitting # of protons 3. Redraw the compound and label equivalent sets of carbons with lower-case letters. Then for each set of carbons give the 5 value and # of carbons it represents. letter δ value # of carbonsarrow_forward
- Nonearrow_forwardCarbohydrates- Draw out the Hawthorne structure for a sugar from the list given in class. Make sure to write out all atoms except for carbons within the ring. Make sure that groups off the carbons in the ring are in the correct orientation above or below the plane. Make sure that bonds are in the correct orientation. Include the full name of the sugar. You can draw out your curve within the text box or upload a drawing below.arrow_forwardHow many milliliters of 97.5(±0.5) wt% H2SO4 with a density of 1.84(±0.01) g/mL will you need to prepare 2.000 L of 0.110 M H2SO4? If the uncertainty in delivering H2SO4 is ±0.01 mL, calculate the absolute uncertainty in the molarity (0.110 M). Assume there is negligible uncertainty in the formula mass of H2SO4 and in the final volume (2.000 L) and assume random error.arrow_forward
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