Textbook Question
Determine which of the heterocyclic amines just shown are aromatic. Give the reasons for your conclusions.
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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 2a,b,c
Draw the structures of the following compounds:
(a) tert-butylamine
(b) α-aminopropionaldehyde
(c) 4-(dimethylamino)pyridine
Verified step by step guidance1
Step 1: Understand the structure of tert-butylamine. The 'tert-butyl' group is a branched alkyl group with the formula (CH₃)₃C-. Attach an amine group (-NH₂) to the central carbon of the tert-butyl group. The resulting structure is (CH₃)₃C-NH₂.
Step 2: Analyze the structure of α-aminopropionaldehyde. The term 'α-amino' indicates that an amine group (-NH₂) is attached to the carbon adjacent to the aldehyde group (-CHO). Start with propionaldehyde (CH₃-CH₂-CHO), and add an amine group to the α-carbon (the carbon next to the aldehyde group).
Step 3: Break down the name 4-(dimethylamino)pyridine. Pyridine is a six-membered aromatic ring containing one nitrogen atom. The '4-' indicates that the substituent is attached to the fourth carbon relative to the nitrogen. The 'dimethylamino' group is -N(CH₃)₂, which is a nitrogen atom bonded to two methyl groups. Attach this group to the fourth carbon of the pyridine ring.
Step 4: Draw the structures for each compound based on the descriptions above. For tert-butylamine, draw a central carbon atom bonded to three methyl groups and one amine group. For α-aminopropionaldehyde, draw a three-carbon chain with an aldehyde group at one end and an amine group on the α-carbon. For 4-(dimethylamino)pyridine, draw a pyridine ring with a dimethylamino group attached to the fourth carbon.
Step 5: Verify the structures by checking that all valencies are satisfied and that the functional groups are correctly placed as per the IUPAC names provided in the problem.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In organic chemistry, recognizing functional groups such as amines, aldehydes, and others is crucial for understanding the properties and reactivity of compounds. For example, tert-butylamine contains an amine group, which influences its basicity and solubility.
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Structural Representation
Structural representation refers to the way in which the arrangement of atoms in a molecule is depicted. This can include Lewis structures, condensed formulas, or skeletal structures. Accurately drawing these structures is essential for visualizing molecular geometry and understanding how different atoms are connected, which is vital for compounds like a-aminopropionaldehyde and 4-(dimethylamino)pyridine.
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Isomerism
Isomerism is the phenomenon where compounds with the same molecular formula can have different structures or arrangements of atoms. This concept is important when drawing organic compounds, as different isomers can exhibit distinct physical and chemical properties. For instance, the presence of different substituents in 4-(dimethylamino)pyridine can lead to various isomeric forms, affecting their reactivity and interactions.
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Related Practice
Textbook Question
Which of the amines listed next is resolved into enantiomers? In each case, explain why interconversion of the enantiomers does or does not take place.
(a) cis-2-methylcyclohexanamine
(b) N-ethyl-N-methylcyclohexanamine
(c) N-methylaziridine
(d) ethylmethylanilinium iodide
(e) methylethylpropylisopropylammoniumiodide
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Textbook Question
Give correct names for the following amines:
(a)
(b)
(c)
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Textbook Question
Draw the structures of the following compounds:
(d) 2-methylaziridine
(e) N-ethyl-N-methylhexan-3-amine
(f) m-chloroaniline
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