Textbook Question
Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.
1456
views
Ch. 20 - Carboxylic Acids
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 20, Problem 11d
Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(d) butan-2-ol → 2-methylbutanoic acid
Verified step by step guidance1
Step 1: Begin by oxidizing butan-2-ol to form the corresponding ketone, butan-2-one. This can be achieved using an oxidizing agent such as PCC (Pyridinium Chlorochromate) or Jones reagent. The reaction involves the removal of two hydrogen atoms from the alcohol group.
Step 2: Perform a nucleophilic addition reaction to introduce a methyl group at the alpha-carbon of butan-2-one. This can be done using a Grignard reagent (e.g., CH3MgBr) or an organolithium reagent, followed by acidic workup to yield 3-methylbutan-2-ol.
Step 3: Oxidize 3-methylbutan-2-ol to form 3-methylbutan-2-one. Use an oxidizing agent such as PCC or Jones reagent to convert the secondary alcohol into a ketone.
Step 4: Perform a haloform reaction to convert 3-methylbutan-2-one into 2-methylbutanoic acid. This reaction involves treating the ketone with excess halogen (e.g., I2 or Br2) in the presence of a base (e.g., NaOH), followed by acidification to yield the carboxylic acid.
Step 5: Purify the 2-methylbutanoic acid product using techniques such as recrystallization or distillation, depending on the physical properties of the compound.
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.
Carboxylic Acid Synthesis
Carboxylic acids can be synthesized through various methods, including oxidation of alcohols. In this case, butan-2-ol can be oxidized to form a carboxylic acid. Understanding the reaction conditions and reagents required for oxidation is crucial for successful synthesis.
Recommended video:
Guided course
04:20
Carboxylic Acids Nomenclature
Oxidation Reactions
Oxidation reactions involve the loss of electrons or an increase in oxidation state, often resulting in the formation of carbonyl compounds or carboxylic acids from alcohols. For butan-2-ol, a common oxidizing agent like potassium dichromate or chromium trioxide can facilitate this transformation.
Recommended video:
Guided course
03:20Benzylic Oxidation
Rearrangement and Isomerization
In organic synthesis, rearrangement and isomerization can lead to the formation of different structural isomers. The target compound, 2-methylbutanoic acid, suggests that the synthesis may involve a rearrangement of the carbon skeleton during the oxidation process, which is essential to achieve the desired product.
Recommended video:
Guided course
06:08Definition of Claisen Rearrangement
Related Practice
Textbook Question
How many stereoisomers are possible for c. a ketotriose?
1796
views
Textbook Question
Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(a) oct-4-yne → butanoic acid
(b) trans-cyclodecene → decanedioic acid
763
views
Textbook Question
Write the mechanism for the base-catalyzed conversion of D-fructose to D-glucose and D-mannose.
1104
views
Textbook Question
Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(e) p-xylene → terephthalic acid
681
views
Textbook Question
Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(f) allyl iodide → but-3-enoic acid
663
views