Domanda del libro di testo
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.
(e)
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Ch.10 - Structure and Synthesis of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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TOC.tableOfContents
- 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
Capitolo 10, Problema 26c
Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
c. 2-methylhexan-3-ol
Guida verificata passo dopo passo1
Identify the target alcohol: The compound 2-methylhexan-3-ol is a secondary alcohol, meaning the hydroxyl group (-OH) is attached to a carbon atom that is bonded to two other carbon atoms. This suggests that the precursor is likely a ketone.
Determine the corresponding carbonyl compound: To synthesize 2-methylhexan-3-ol, the corresponding carbonyl compound would be 2-methylhexan-3-one. This is because reducing a ketone with a reducing agent will yield a secondary alcohol.
Choose an appropriate reducing agent: Common reducing agents for converting ketones to secondary alcohols include sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄). NaBH₄ is often preferred for mild conditions.
Write the reaction mechanism: The reduction involves the nucleophilic attack of the hydride ion (H⁻) from the reducing agent on the carbonyl carbon of 2-methylhexan-3-one. This forms an alkoxide intermediate, which is then protonated by water or an acid to yield 2-methylhexan-3-ol.
Summarize the synthesis: Start with 2-methylhexan-3-one as the carbonyl compound. Treat it with NaBH₄ in a suitable solvent (e.g., ethanol or methanol) to reduce the ketone to 2-methylhexan-3-ol. Finally, perform a workup step to isolate the alcohol product.
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Reduction of Carbonyl Compounds
Reduction is a chemical reaction that involves the gain of electrons or a decrease in oxidation state. In organic chemistry, carbonyl compounds, such as aldehydes and ketones, can be reduced to alcohols using reducing agents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4). Understanding the mechanism of this reduction is crucial for synthesizing alcohols from carbonyl precursors.
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01:40
Defining meso compounds.
Structure of 2-methylhexan-3-ol
2-methylhexan-3-ol is a secondary alcohol with a specific carbon skeleton. It consists of a six-carbon chain (hexane) with a methyl group (–CH3) attached to the second carbon and a hydroxyl group (–OH) on the third carbon. Recognizing the structure helps in identifying the appropriate carbonyl compound to reduce in order to achieve the desired alcohol.
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03:04Drawing Resonance Structures
Choice of Carbonyl Compound
To synthesize 2-methylhexan-3-ol, one must select the correct carbonyl compound to reduce. The appropriate precursor is 2-methylhexan-3-one, a ketone, which upon reduction will yield the target alcohol. Understanding the relationship between the structure of the desired alcohol and its corresponding carbonyl compound is essential for successful synthesis.
Video consigliato:
01:40Defining meso compounds.
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