Textbook Question
Draw the products of the following reactions:
a.
3
views
Ch. 17 - Reactions at the Alpha-Carbon
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 18, Problem 52
Which of the following compounds decarboxylates when heated?
Verified step by step guidance1
Step 1: Understand the concept of decarboxylation. Decarboxylation is the removal of a carboxyl group (-COOH) from a molecule, typically releasing carbon dioxide (CO₂). This reaction often occurs in compounds with a β-keto acid or a carboxylic acid group adjacent to a carbonyl group.
Step 2: Analyze compound (i). This compound contains two carboxylic acid groups (-COOH) attached to a cyclohexane ring. However, neither of these carboxylic acid groups is adjacent to a carbonyl group, which is necessary for decarboxylation to occur under heating.
Step 3: Analyze compound (ii). This compound has a carboxylic acid group (-COOH) adjacent to a ketone group (C=O). This structure is characteristic of a β-keto acid, which readily undergoes decarboxylation when heated.
Step 4: Analyze compound (iii). This compound contains a hydroxyl group (-OH) and a carboxylic acid group (-COOH) attached to a cyclohexane ring. However, the carboxylic acid group is not adjacent to a carbonyl group, so it does not decarboxylate under heating.
Step 5: Analyze compound (iv). This compound contains two ketone groups (C=O) attached to a cyclohexane ring but lacks a carboxylic acid group (-COOH). Decarboxylation requires the presence of a carboxylic acid group, so this compound does not undergo decarboxylation.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Decarboxylation
Decarboxylation is a chemical reaction that involves the removal of a carboxyl group (-COOH) from a molecule, resulting in the release of carbon dioxide (CO2). This process is often facilitated by heat and is common in organic compounds containing carboxylic acids. Understanding the conditions under which decarboxylation occurs is crucial for predicting the behavior of organic compounds when heated.
Recommended video:
Guided course
02:32
Predict the correct structure
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 and can undergo various reactions, including decarboxylation. Identifying the presence of carboxylic acid functional groups in the given compounds is essential for determining which compounds are likely to decarboxylate upon heating.
Recommended video:
Guided course
04:20Carboxylic Acids Nomenclature
Thermal Stability of Functional Groups
The thermal stability of functional groups refers to their ability to withstand heat without undergoing decomposition or reaction. Different functional groups have varying stabilities; for instance, carboxylic acids can decarboxylate when heated, while other groups may not. Analyzing the structures of the compounds in the question helps assess their thermal stability and predict their behavior under heat.
Recommended video:
Guided course
02:36Identifying Functional Groups
Related Practice
Textbook Question
Draw the products of the following reactions:
d. diethyl 1,2-benzenedicarboxylate + sodium ethoxide: (1) slow addition of ethyl acetate; (2) HCl
4
views
Textbook Question
Draw the products of the following reactions:
b.
4
views
Textbook Question
Draw the products of the following reactions:
c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl
1
views
Textbook Question
Draw the products of the following reactions: e. diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + heat
5
views
Textbook Question
The 1H NMR chemical shifts of nitromethane, dinitromethane, and trinitromethane are at δ6.10, δ4.33, and δ7.52. Match each chemical shift with the compound. Explain how chemical shift correlates with pKa.
5
views