Textbook Question
Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.
(d) PhNHCOCH2CH(CH3)2
(e) CH3CONHCH2Ph
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Ch. 21 - Carboxylic Acid Derivatives
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 21, Problem 1a,b,c
Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.
(a) PhCOOCH2CH(CH3)2
(b) PhOCHO
(c) PhCH(CH3)COOCH3
Verified step by step guidance1
Step 1: Analyze the structure in part (a), PhCOOCH2CH(CH3)2. This is an ester derived from benzoic acid (PhCOOH) and isopropyl alcohol (CH2CH(CH3)2). The common name is formed by naming the alcohol part first (isopropyl) followed by the acid part (benzoate). The IUPAC name is formed by naming the alcohol part as 'isopropyl' and the acid part as 'benzoate'.
Step 2: Examine the structure in part (b), PhOCHO. This is an aromatic aldehyde derivative where the benzene ring (Ph) is attached to a formyl group (-CHO). The common name is benzaldehyde. The IUPAC name is also benzaldehyde, as it is a simple aromatic aldehyde.
Step 3: Analyze the structure in part (c), PhCH(CH3)COOCH3. This is an ester derived from 2-phenylpropanoic acid (PhCH(CH3)COOH) and methanol (CH3OH). The common name is formed by naming the alcohol part first (methyl) followed by the acid part (2-phenylpropanoate). The IUPAC name is methyl 2-phenylpropanoate.
Step 4: For each structure, ensure you understand the naming conventions for carboxylic acid derivatives. Esters are named by identifying the alcohol-derived alkyl group first, followed by the acid-derived part with the suffix '-oate'. Aldehydes are named by replacing the '-e' in the parent alkane name with '-al'.
Step 5: Practice identifying functional groups and naming similar compounds to reinforce your understanding of carboxylic acid derivative nomenclature. Pay attention to the substituents and their positions on the parent chain or ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carboxylic Acid Derivatives
Carboxylic acid derivatives are compounds that are derived from carboxylic acids by replacing the hydroxyl group (-OH) with another functional group. Common derivatives include esters, amides, anhydrides, and acyl chlorides. Understanding the structure and reactivity of these derivatives is crucial for naming and identifying them correctly.
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IUPAC Nomenclature
IUPAC nomenclature is a systematic method for naming organic chemical compounds. It provides rules for naming based on the structure of the molecule, including the longest carbon chain, functional groups, and substituents. Familiarity with these rules is essential for accurately naming carboxylic acid derivatives and distinguishing between common and systematic names.
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Common Names vs. IUPAC Names
Common names are traditional names that may not follow systematic naming conventions, while IUPAC names are derived from a set of standardized rules. For carboxylic acid derivatives, common names often reflect historical usage or structural features, whereas IUPAC names provide a clear, unambiguous description of the compound's structure. Recognizing both naming conventions is important for effective communication in organic chemistry.
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