Textbook Question
Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.
(e)
1
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Ch. 18 - Ketones and Aldehydes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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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 18, Problem 47f
Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.
(f) 
Verified step by step guidance1
Step 1: Analyze the starting material and product. The starting material is a cyclic ester (lactone), and the product is a cyclic ketone with an alcohol group on the adjacent carbon. This suggests a ring-opening reaction followed by reduction and functional group transformation.
Step 2: Perform a nucleophilic ring-opening of the lactone. Use a nucleophile such as ethylene glycol (HOCH2CH2OH) in the presence of a base like sodium hydroxide (NaOH) to open the lactone ring and form a hydroxy acid intermediate.
Step 3: Decarboxylate the hydroxy acid intermediate. Heat the intermediate under acidic conditions to remove the carboxylic acid group and form the cyclic ketone structure.
Step 4: Introduce the alcohol group on the adjacent carbon. Use a Grignard reagent (e.g., CH3MgBr) to add a methyl group to the ketone, followed by hydrolysis to form the secondary alcohol.
Step 5: Purify the product. Use techniques such as recrystallization or distillation to isolate the desired cyclic ketone with the alcohol group in good yield.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Cyclic Ketones
Cyclic ketones are organic compounds characterized by a carbonyl group (C=O) attached to a carbon atom within a ring structure. Their reactivity is influenced by the ring strain and the presence of substituents. Understanding the structure and reactivity of cyclic ketones is crucial for predicting the outcomes of synthetic transformations, such as reduction reactions.
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02:27
Name the ketone
DIBAL-H (Diisobutylaluminum Hydride)
DIBAL-H is a selective reducing agent commonly used in organic synthesis to convert esters and ketones to aldehydes and alcohols. It operates under mild conditions and is particularly effective for reducing cyclic ketones to alcohols without over-reduction. Knowledge of DIBAL-H's mechanism and selectivity is essential for planning efficient synthetic routes.
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Reduction Reactions
Reduction reactions involve the gain of electrons or hydrogen, leading to a decrease in oxidation state. In organic chemistry, these reactions often convert carbonyl compounds to alcohols. Understanding the principles of reduction, including the choice of reducing agents and reaction conditions, is vital for achieving high yields in synthetic conversions.
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Related Practice
Textbook Question
For each compound,
1. name the functional group.
2. show what compound(s) result from complete hydrolysis.
(a)
1
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Textbook Question
Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.
(c)
1
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Textbook Question
Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.
(g)
1
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Textbook Question
Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.
(h)
1
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Textbook Question
Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.
(d)
2
views