Textbook Question
Show how you would convert aniline to the following compounds.
(f) benzonitrile
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Ch. 19 - Amines
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 19, Problem 26a,b,c
Show how to synthesize the following amines from the indicated starting materials by reductive amination.
(a) benzylmethylamine from benzaldehyde
(b) N-benzylpiperidine from piperidine
(c) N-cyclohexylaniline from cyclohexanone
Verified step by step guidance1
Step 1: Understand the concept of reductive amination. Reductive amination is a reaction where an aldehyde or ketone reacts with an amine to form an imine intermediate, which is then reduced to form an amine. The reduction step typically uses a reducing agent like sodium cyanoborohydride (NaBH3CN) or hydrogen with a catalyst.
Step 2: For part (a), benzylmethylamine from benzaldehyde: Start with benzaldehyde (C6H5CHO) as the starting material. React benzaldehyde with methylamine (CH3NH2) to form an imine intermediate. The imine has the structure C6H5CH=NHCH3. Then, reduce the imine using a reducing agent like NaBH3CN to form benzylmethylamine (C6H5CH2NHCH3).
Step 3: For part (b), N-benzylpiperidine from piperidine: Start with piperidine (C5H11N) as the amine and benzaldehyde (C6H5CHO) as the aldehyde. React benzaldehyde with piperidine to form an imine intermediate with the structure C6H5CH=N(C5H10). Reduce this imine using NaBH3CN to form N-benzylpiperidine (C6H5CH2N(C5H10)).
Step 4: For part (c), N-cyclohexylaniline from cyclohexanone: Start with cyclohexanone (C6H10O) as the ketone and aniline (C6H5NH2) as the amine. React cyclohexanone with aniline to form an imine intermediate with the structure C6H10=NC6H5. Reduce this imine using NaBH3CN to form N-cyclohexylaniline (C6H11NHC6H5).
Step 5: Summarize the general process for reductive amination: (1) React the aldehyde or ketone with the amine to form an imine intermediate. (2) Use a mild reducing agent like NaBH3CN to selectively reduce the imine to the desired amine product. Ensure proper reaction conditions (e.g., pH control) to avoid side reactions.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reductive Amination
Reductive amination is a chemical reaction that involves the conversion of a carbonyl compound (like an aldehyde or ketone) into an amine. This process typically includes the formation of an imine or enamine intermediate, which is then reduced to yield the desired amine. Common reducing agents used in this reaction include sodium cyanoborohydride or hydrogen in the presence of a catalyst.
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Carbonyl Compounds
Carbonyl compounds, which include aldehydes and ketones, are characterized by the presence of a carbonyl group (C=O). In the context of reductive amination, these compounds serve as the starting materials that react with amines to form imines. Understanding the reactivity and properties of carbonyl compounds is crucial for predicting the outcomes of synthetic pathways involving amine formation.
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Amine Structure and Reactivity
Amines are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. Their structure influences their reactivity, particularly in nucleophilic reactions. In reductive amination, the nucleophilic nature of amines allows them to attack the electrophilic carbon of carbonyl compounds, leading to the formation of imine intermediates essential for synthesizing various amines.
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Related Practice
Textbook Question
Show how to synthesize the following amines from the indicated starting materials by reductive amination.
(e)
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Textbook Question
Show how you would convert aniline to the following compounds.
(d) bromobenzene
(e) iodobenzene
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Textbook Question
Show how you would convert aniline to the following compounds.
(g) phenol
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Textbook Question
Addition of one equivalent of ammonia to 1-bromoheptane gives a mixture of heptan-1-amine, some dialkylamine, some trialkylamine, and even some tetraalkylammonium bromide.
(a) Give a mechanism to show how this reaction takes place, as far as the dialkylamine.
(b) How would you modify the procedure to get an acceptable yield of heptan-1-amine?
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Textbook Question
Show how to synthesize the following amines from the indicated starting materials by acylation–reduction.
(a) N-butylpiperidine from piperidine
(b) N-benzylaniline from aniline
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