Textbook Question
Draw the structures of the following carboxylic acids.
(e) trans-2-methylcyclohexanecarboxylic acid
(f) 2,3-dimethylfumaric acid
(g) m-chlorobenzoic acid
(h) 3-methylphthalic acid
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Ch. 20 - Carboxylic Acids
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 20, Problem 1a-d
Draw the structures of the following carboxylic acids.
(a) α-methylbutyric acid
(b) 2-bromobutanoic acid
(c) 4-aminopentanoic acid
(d) cis-4-phenylbut-2-enoic acid
Verified step by step guidance1
Step 1: Understand the naming conventions of carboxylic acids. The suffix '-oic acid' indicates the presence of a carboxyl group (-COOH). The prefix or substituents describe the additional groups attached to the main carbon chain. Begin by identifying the parent chain and the substituents for each compound.
Step 2: For (a) α-methylbutyric acid: The parent chain is butyric acid (4 carbons with a -COOH group at one end). The term 'α-methyl' indicates a methyl group (-CH₃) attached to the carbon adjacent to the carboxyl group. Draw the structure with the carboxyl group at one end and a methyl group on the α-carbon.
Step 3: For (b) 2-bromobutanoic acid: The parent chain is butanoic acid (4 carbons with a -COOH group at one end). The '2-bromo' indicates a bromine atom attached to the second carbon in the chain. Draw the structure with the carboxyl group at one end and a bromine atom on the second carbon.
Step 4: For (c) 4-aminopentanoic acid: The parent chain is pentanoic acid (5 carbons with a -COOH group at one end). The '4-amino' indicates an amino group (-NH₂) attached to the fourth carbon in the chain. Draw the structure with the carboxyl group at one end and an amino group on the fourth carbon.
Step 5: For (d) cis-4-phenylbut-2-enoic acid: The parent chain is but-2-enoic acid (4 carbons with a -COOH group at one end and a double bond between carbons 2 and 3). The '4-phenyl' indicates a phenyl group (C₆H₅) attached to the fourth carbon. The 'cis' configuration means the substituents on the double bond are on the same side. Draw the structure with the carboxyl group at one end, a double bond between carbons 2 and 3, and a phenyl group on the fourth carbon in the cis configuration.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carboxylic Acids
Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). This functional group consists of a carbon atom double-bonded to an oxygen atom and single-bonded to a hydroxyl group (-OH). Carboxylic acids are known for their acidic properties and are commonly found in various biological and industrial processes.
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Carboxylic Acids Nomenclature
Nomenclature of Organic Compounds
The nomenclature of organic compounds follows specific rules set by the International Union of Pure and Applied Chemistry (IUPAC). This includes identifying the longest carbon chain, determining the functional groups, and assigning locants to substituents. Understanding these rules is essential for accurately naming and drawing the structures of organic molecules, including carboxylic acids.
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Structural Isomerism
Structural isomerism occurs when compounds have the same molecular formula but differ in the arrangement of atoms. In the context of the question, different carboxylic acids can exhibit structural isomerism through variations in the position of functional groups or the branching of carbon chains. Recognizing these isomers is crucial for drawing the correct structures of the specified acids.
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