Textbook Question
Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.
(g) KOH + CH3CH2OH ⇌
871
views
Ch.10 - Structure and Synthesis of Alcohols
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 10, Problem 43b
Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.
(b) 1-cyclohexylpropan-1-ol
Verified step by step guidance1
Step 1: Identify the target alcohol structure, 1-cyclohexylpropan-1-ol. This alcohol contains a cyclohexyl group attached to a propan-1-ol backbone, indicating the presence of a primary alcohol functional group.
Step 2: Determine the precursor carbonyl compound. To form a primary alcohol, the precursor is typically an aldehyde. In this case, the precursor would be 1-cyclohexylpropanal, which has the same carbon skeleton but with a carbonyl group (C=O) at the terminal carbon.
Step 3: Select an appropriate reducing agent. Common reducing agents for converting aldehydes to primary alcohols include sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄). NaBH₄ is milder and often used in protic solvents, while LiAlH₄ is stronger and requires anhydrous conditions.
Step 4: Write the reaction mechanism. The reducing agent donates hydride ions (H⁻) to the carbonyl carbon of the aldehyde, breaking the C=O double bond and forming a C-H bond. Simultaneously, the oxygen atom gains a proton (H⁺) from the solvent or reaction medium, resulting in the formation of the alcohol.
Step 5: Ensure stereochemistry and regioselectivity. Since the target alcohol does not have stereocenters, stereochemistry is not a concern in this case. The reaction proceeds regioselectively to form the desired primary alcohol without side reactions.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
4mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carbonyl Compounds
Carbonyl compounds are organic molecules that contain a carbon atom double-bonded to an oxygen atom (C=O). They include aldehydes, ketones, and carboxylic acids. Understanding the structure and reactivity of carbonyl compounds is crucial, as they serve as key intermediates in organic synthesis, particularly in the formation of alcohols through reduction reactions.
Recommended video:
Guided course
01:40
Defining meso compounds.
Reducing Agents
Reducing agents are substances that donate electrons to another species, thereby reducing its oxidation state. Common reducing agents for carbonyl compounds include lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4). These agents are essential for converting carbonyl groups into alcohols, making them vital in organic synthesis.
Recommended video:
Guided course
09:28Reducing Agents
Synthesis of Alcohols
The synthesis of alcohols from carbonyl compounds typically involves reduction reactions. In the case of 1-cyclohexylpropan-1-ol, a ketone or aldehyde can be reduced using an appropriate reducing agent. Understanding the mechanism of these reactions, including the role of the reducing agent and the type of carbonyl compound used, is essential for successfully synthesizing the desired alcohol.
Recommended video:
Guided course
02:26Forming alcohols through Oxymercuration-Reduction.
Related Practice
Textbook Question
Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.
(f) (CH3)3C–O– + H2O ⇌
954
views
Textbook Question
Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.
(a) octan-1-ol
1232
views
Textbook Question
Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.
(a)
1269
views
Textbook Question
Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.
(c) 1-phenylbutan-1-ol
(d)
621
views
Textbook Question
Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.
(e)
(f)
601
views