Ch.10 - Structure and Synthesis of Alcohols

Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo

Wade 9th Edition

Ch.10 - Structure and Synthesis of Alcohols

Problema 26d

Capitolo 10, Problema 26d

Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
(d)

Guida verificata passo dopo passo

Step 1: Analyze the target molecule. The structure contains a secondary alcohol group (-OH) attached to a cyclohexane ring and an ester functional group. The alcohol group likely originates from the reduction of a carbonyl compound.

Step 2: Identify the precursor carbonyl compound. To synthesize the secondary alcohol, the precursor is likely a ketone. The ketone would have the same cyclohexane ring structure with a carbonyl group (C=O) at the position where the alcohol is now located.

Step 3: Select an appropriate reducing agent. Common reducing agents for converting ketones to secondary alcohols include sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄). NaBH₄ is typically used for mild reductions, while LiAlH₄ is more reactive and can reduce esters as well.

Step 4: Perform the reduction reaction. Treat the ketone precursor with the chosen reducing agent in a suitable solvent (e.g., ethanol or tetrahydrofuran). This will convert the carbonyl group into the secondary alcohol group.

Step 5: Verify the product. After the reduction, confirm the structure of the synthesized alcohol using spectroscopic techniques such as NMR or IR to ensure the correct functional groups are present and the desired alcohol has been formed.

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Reduction of Carbonyl Compounds

Reduction of carbonyl compounds involves the conversion of a carbonyl group (C=O) into an alcohol (C-OH) by adding hydrogen or removing oxygen. Common reducing agents include lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4). Understanding the mechanism of this reaction is crucial for synthesizing alcohols from ketones or aldehydes.

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Types of Carbonyl Compounds

Carbonyl compounds can be classified into aldehydes and ketones, which differ in their structure and reactivity. Aldehydes have at least one hydrogen atom attached to the carbonyl carbon, while ketones have two carbon groups. Identifying the correct type of carbonyl compound is essential for determining the appropriate reduction method to synthesize the desired alcohol.

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Stereochemistry of Alcohols

Stereochemistry refers to the spatial arrangement of atoms in molecules and is particularly important in organic synthesis. Alcohols can exist as chiral molecules, leading to different enantiomers. When synthesizing an alcohol from a carbonyl compound, it is important to consider the stereochemical outcome, as it can affect the properties and reactivity of the final product.

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Authentic skunk spray has become valuable for use in scent-masking products. Show how you would synthesize the major component of skunk spray (3-methylbutane-1-thiol and but-2-ene-1-thiol) from any of the readily available butene or from buta-1,3-diene.

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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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Give IUPAC names for the following compounds.

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Arrange the following compounds in order of decreasing acidity.

CH₃COOH, CH₃OH, CH₃CH₃, CH₃SO₃H, CH₃NH₂, CH₃SH, CH₃C≡CH