Textbook Question
Predict the products you would expect from the reaction of LiALH4 followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(c) Ph-COOH
13. Alcohols and Carbonyl Compounds
Reducing Agent
4:35 minutesProblem 43b
Textbook Question
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.
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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.
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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.
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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.
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