(a) Interpretation: The amine among 2, 2-dimethyl-1-propanamine , 3-methyl-1-pentanamine , or N -butylaniline that can be prepared from the Gabriel synthesis or Staudinger reaction is to be stated. Concept introduction: Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines . Aromatic amines cannot be prepared by this reaction. Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

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Answer 1

Question

Chapter 23, Problem 23.35P

Interpretation Introduction

(a)

Interpretation:

The amine among 2, 2-dimethyl-1-propanamine, 3-methyl-1-pentanamine, or N-butylaniline that can be prepared from the Gabriel synthesis or Staudinger reaction is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Interpretation Introduction

(b)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Gabriel synthesis method is to be proposed.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Interpretation Introduction

(c)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Staudinger reaction method is to be proposed.

Concept introduction:

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Interpretation Introduction

(d)

Interpretation:

The reason as to why, 2, 2-dimethyl-1-propanamine, and N-butylaniline cannot be prepared by Gabriel synthesis and Staudinger reaction method is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

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Transmitance 3. Which one of the following compounds corresponds to this IR spectrum? Point out the absorption band(s) that helped you decide. OH H3C OH H₂C CH3 H3C CH3 H3C INFRARED SPECTRUM 0.8- 0.6 0.4- 0.2 3000 2000 1000 Wavenumber (cm-1) 4. Consider this compound: H3C On the structure above, label the different types of H's as A, B, C, etc. In table form, list the labeled signals, and for each one state the number of hydrogens, their shifts, and the splitting you would observe for these hydrogens in the ¹H NMR spectrum. Label # of hydrogens splitting Shift (2)

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Answer 2

Question

Chapter 23, Problem 23.35P

Interpretation Introduction

(a)

Interpretation:

The amine among 2, 2-dimethyl-1-propanamine, 3-methyl-1-pentanamine, or N-butylaniline that can be prepared from the Gabriel synthesis or Staudinger reaction is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Interpretation Introduction

(b)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Gabriel synthesis method is to be proposed.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Interpretation Introduction

(c)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Staudinger reaction method is to be proposed.

Concept introduction:

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Interpretation Introduction

(d)

Interpretation:

The reason as to why, 2, 2-dimethyl-1-propanamine, and N-butylaniline cannot be prepared by Gabriel synthesis and Staudinger reaction method is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

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Answer 3

Question

Chapter 23, Problem 23.35P

Interpretation Introduction

(a)

Interpretation:

The amine among 2, 2-dimethyl-1-propanamine, 3-methyl-1-pentanamine, or N-butylaniline that can be prepared from the Gabriel synthesis or Staudinger reaction is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Interpretation Introduction

(b)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Gabriel synthesis method is to be proposed.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Interpretation Introduction

(c)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Staudinger reaction method is to be proposed.

Concept introduction:

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Interpretation Introduction

(d)

Interpretation:

The reason as to why, 2, 2-dimethyl-1-propanamine, and N-butylaniline cannot be prepared by Gabriel synthesis and Staudinger reaction method is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

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Answer 4

Question

Chapter 23, Problem 23.35P

Interpretation Introduction

(a)

Interpretation:

The amine among 2, 2-dimethyl-1-propanamine, 3-methyl-1-pentanamine, or N-butylaniline that can be prepared from the Gabriel synthesis or Staudinger reaction is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Interpretation Introduction

(b)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Gabriel synthesis method is to be proposed.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Interpretation Introduction

(c)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Staudinger reaction method is to be proposed.

Concept introduction:

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Interpretation Introduction

(d)

Interpretation:

The reason as to why, 2, 2-dimethyl-1-propanamine, and N-butylaniline cannot be prepared by Gabriel synthesis and Staudinger reaction method is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

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Answer 5

Chapter 23, Problem 23.35P

Interpretation Introduction

(a)

Interpretation:

The amine among 2, 2-dimethyl-1-propanamine, 3-methyl-1-pentanamine, or N-butylaniline that can be prepared from the Gabriel synthesis or Staudinger reaction is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Interpretation Introduction

(b)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Gabriel synthesis method is to be proposed.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Interpretation Introduction

(c)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Staudinger reaction method is to be proposed.

Concept introduction:

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Interpretation Introduction

(d)

Interpretation:

The reason as to why, 2, 2-dimethyl-1-propanamine, and N-butylaniline cannot be prepared by Gabriel synthesis and Staudinger reaction method is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Answer 6

Chapter 23, Problem 23.35P

Interpretation Introduction

(a)

Interpretation:

The amine among 2, 2-dimethyl-1-propanamine, 3-methyl-1-pentanamine, or N-butylaniline that can be prepared from the Gabriel synthesis or Staudinger reaction is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Answer 7

Chapter 23, Problem 23.35P

Interpretation Introduction

(a)

Interpretation:

The amine among 2, 2-dimethyl-1-propanamine, 3-methyl-1-pentanamine, or N-butylaniline that can be prepared from the Gabriel synthesis or Staudinger reaction is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Gabriel synthesis method is to be proposed.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Gabriel synthesis method is to be proposed.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Staudinger reaction method is to be proposed.

Concept introduction:

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The synthesis of 3-methyl-1-pentanamine from an alkyl halide by using Staudinger reaction method is to be proposed.

Concept introduction:

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The reason as to why, 2, 2-dimethyl-1-propanamine, and N-butylaniline cannot be prepared by Gabriel synthesis and Staudinger reaction method is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The reason as to why, 2, 2-dimethyl-1-propanamine, and N-butylaniline cannot be prepared by Gabriel synthesis and Staudinger reaction method is to be stated.

Concept introduction:

Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.

Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 23 - Prob. 23.1P Ch. 23 - Prob. 23.2P Ch. 23 - Prob. 23.3P Ch. 23 - Prob. 23.4P Ch. 23 - Prob. 23.5P Ch. 23 - Prob. 23.6P Ch. 23 - Prob. 23.7P Ch. 23 - Prob. 23.8P Ch. 23 - Prob. 23.9P Ch. 23 - Prob. 23.10P

Solution Summary: The author explains that the amine can be prepared by Gabriel synthesis or Staudinger reaction.

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Chapter 23 Solutions