Textbook Question
For each heterocyclic compound,
(i) explain what type of acid derivative is present.
(ii) show what compounds would result from complete hydrolysis.
(iii) are any of the rings aromatic? Explain.
(e)
2
views
Ch. 21 - Carboxylic Acid Derivatives
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 41a,b,c(ii)
For each heterocyclic compound,
(ii) show what compounds would result from complete hydrolysis.
(a) 
(b) 
(c) 
Verified step by step guidance1
Step 1: Analyze the structure of compound (a), which is phthalic anhydride. Hydrolysis of anhydrides involves breaking the anhydride bond with water, resulting in two carboxylic acid groups. Write the reaction: \( \text{C_6H_4(CO)_2O} + H_2O \rightarrow \text{C_6H_4(COOH)_2} \).
Step 2: Examine compound (b), which is thiophene-2-carboxylic acid. Hydrolysis of thiophene derivatives typically involves breaking the bond between the sulfur atom and the carbonyl group. The product will be thiophene and a carboxylic acid group. Write the reaction: \( \text{C_4H_3S(CO)} + H_2O \rightarrow \text{C_4H_3S} + \text{COOH} \).
Step 3: Look at compound (c), which is a lactam (cyclic amide). Hydrolysis of lactams involves breaking the amide bond with water, resulting in an amine and a carboxylic acid. Write the reaction: \( \text{C_5H_9NO} + H_2O \rightarrow \text{C_5H_{10}NH_2} + \text{COOH} \).
Step 4: For each compound, ensure the hydrolysis reaction is balanced and consistent with the functional groups present in the heterocyclic structure. Verify that water is the reagent breaking the bonds.
Step 5: Summarize the products: (a) phthalic acid, (b) thiophene and carboxylic acid, (c) amine and carboxylic acid. These are the expected results from complete hydrolysis of the given heterocyclic compounds.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
1mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Heterocyclic Compounds
Heterocyclic compounds are cyclic structures that contain at least one atom other than carbon in the ring, such as nitrogen, oxygen, or sulfur. These compounds are significant in organic chemistry due to their diverse chemical properties and biological activities. Understanding their structure is crucial for predicting their reactivity, especially during hydrolysis reactions.
Recommended video:
2:06
Nomenclature of Heterocycles Concept 1
Hydrolysis Reactions
Hydrolysis is a chemical reaction involving the breakdown of a compound by water, often catalyzed by an acid or base. In the context of heterocyclic compounds, hydrolysis can lead to the formation of various products, including amines, alcohols, or carboxylic acids, depending on the functional groups present. Recognizing the conditions and mechanisms of hydrolysis is essential for predicting the products formed.
Recommended video:
3:09Triacylglycerol Reactions: Hydrolysis Concept 3
Acid-Catalyzed Reactions
Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction, often by protonating a reactant to make it more reactive. In the case of ester hydrolysis, the acid catalyst helps to break the ester bond, facilitating the conversion of the ester into its corresponding alcohol and acid. Understanding the role of the acid catalyst is vital for analyzing the reaction pathway and the resulting products.
Recommended video:
Guided course
03:09Acid Catalyzed
Related Practice
Textbook Question
For each heterocyclic compound,
(i) explain what type of acid derivative is present.
(ii) show what compounds would result from complete hydrolysis.
(iii) are any of the rings aromatic? Explain.
(d)
3
views
Textbook Question
Propose a mechanism for the reaction of methyl isocyanate with 1-naphthol to give Sevin® insecticide.
3
views
Textbook Question
For each heterocyclic compound,
(i) explain what type of acid derivative is present.
(a)
(b)
(c)
2
views
Textbook Question
For each heterocyclic compound,
(iii) are any of the rings aromatic? Explain.
(a)
(b)
(c)
37
views
Textbook Question
For each heterocyclic compound,
(i) explain what type of acid derivative is present.
(ii) show what compounds would result from complete hydrolysis.
(iii) are any of the rings aromatic? Explain.
(f)
1
views