Textbook Question
Rank the compounds in each set in order of increasing acid strength.
(a) CH3CH2COOH, CH3CHBrCOOH, CH3CBr2COOH
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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 2a,b,c
Name the following carboxylic acids (when possible, give both a common name and a systematic name).
(a) 
(b) 
(c) 
Verified step by step guidance1
Step 1: Analyze the structure in (i). The molecule contains a carboxylic acid group (-COOH) attached to a chain of four carbon atoms. The chain is substituted with a bromine atom and a methyl group. Identify the longest chain containing the carboxylic acid group and number the chain starting from the carbon of the carboxylic acid group.
Step 2: For (i), assign the position of the substituents (bromine and methyl group) based on the numbering. The systematic name will be derived by combining the substituent names with their positions and the base name of the carboxylic acid. The common name can be derived based on traditional naming conventions for carboxylic acids.
Step 3: Analyze the structure in (ii). The molecule contains a carboxylic acid group (-COOH) attached to a chain of six carbon atoms. The chain includes a double bond and a methyl group as substituents. Identify the longest chain containing the carboxylic acid group and the double bond, and number the chain starting from the carbon of the carboxylic acid group.
Step 4: For (ii), assign the position of the double bond and the methyl group based on the numbering. The systematic name will include the position of the double bond (using 'E' or 'Z' configuration if stereochemistry is specified) and the substituent name. The common name can be derived based on traditional naming conventions for carboxylic acids.
Step 5: Analyze the structure in (iii). The molecule contains a benzene ring with a carboxylic acid group (-COOH) and two bromine atoms as substituents. Number the benzene ring starting from the carbon of the carboxylic acid group and assign positions to the bromine atoms. The systematic name will include the positions of the bromine atoms and the carboxylic acid group. The common name can be derived based on traditional naming conventions for aromatic carboxylic acids.
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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 one or more carboxyl groups (-COOH). They are known for their acidic properties due to the ability of the carboxyl group to donate a proton (H+). Common examples include acetic acid (ethanoic acid) and benzoic acid. Understanding their structure is crucial for naming and identifying these compounds.
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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). For carboxylic acids, the systematic name is derived from the longest carbon chain containing the carboxyl group, with the suffix '-oic acid' added. Common names may also be used, often based on historical or traditional names, which can differ from systematic naming.
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Substituents and Their Effects on Naming
Substituents are atoms or groups of atoms that replace hydrogen atoms in a hydrocarbon chain. In naming carboxylic acids, the presence of substituents such as halogens (e.g., Br) or alkyl groups affects the numbering of the carbon chain and the overall name. It is essential to identify and correctly position these substituents to derive the accurate systematic name of the compound.
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Related Practice
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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Textbook Question
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
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Textbook Question
Rank the compounds in each set in order of increasing acid strength.
(b) CH3CH2CH2CHBrCOOH, CH3CH2CHBrCH2COOH, CH3CHBrCH2CH2COOH
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Textbook Question
Name the following carboxylic acids (when possible, give both a common name and a systematic name).
(d)
(e)
(f)
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