Textbook Question
Predict the products of the following reactions:
(e)
(f)
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 11a
Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.
(a) 
Verified step by step guidance1
Step 1: Identify the starting material and the target product. The starting material is benzaldehyde (Ph-CHO), and the target product is benzophenone (Ph-C(O)-Ph). This transformation involves converting an aldehyde into a ketone.
Step 2: Recognize the type of reaction required. To achieve this transformation, you need to add a phenyl group (Ph) to the carbonyl carbon of benzaldehyde. This can be accomplished using a nucleophilic addition reaction followed by oxidation.
Step 3: Select appropriate reagents for the nucleophilic addition step. A Grignard reagent, such as phenylmagnesium bromide (Ph-MgBr), can be used to add the phenyl group to the carbonyl carbon. The reaction proceeds via the formation of a tetrahedral intermediate.
Step 4: After the addition of the Grignard reagent, the intermediate formed is an alcohol (Ph-C(OH)-Ph). To convert this alcohol into the ketone, an oxidation step is required. Suitable oxidizing agents include PCC (pyridinium chlorochromate) or Jones reagent (CrO3/H2SO4).
Step 5: Combine the steps. First, react benzaldehyde with phenylmagnesium bromide in an appropriate solvent like diethyl ether to form the alcohol intermediate. Then, oxidize the intermediate using PCC or another oxidizing agent to yield benzophenone.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Benzaldehyde
Benzaldehyde (Ph-CHO) is an aromatic aldehyde characterized by the presence of a formyl group (-CHO) attached to a phenyl group (Ph). It serves as a key starting material in organic synthesis due to its reactivity, particularly in nucleophilic addition reactions. Understanding its structure and reactivity is essential for converting it into other functional groups, such as ketones.
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Aldol Condensation
Aldol condensation is a fundamental reaction in organic chemistry where aldehydes or ketones with alpha-hydrogens react to form β-hydroxy aldehydes or ketones. This reaction can lead to the formation of larger carbon skeletons and is crucial for synthesizing complex molecules. In the context of the conversion from benzaldehyde to a ketone, this reaction can facilitate the formation of the desired product through subsequent dehydration.
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Reagents and Solvents
The choice of reagents and solvents is critical in organic synthesis as they influence the reaction pathway, yield, and selectivity of the desired product. Common reagents for converting aldehydes to ketones include Grignard reagents or organolithium compounds, which can add to the carbonyl carbon. Understanding the role of these reagents and the appropriate conditions for the reaction is essential for successfully achieving the conversion depicted in the question.
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Related Practice
Textbook Question
Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.
(b)
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Textbook Question
Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.
(d)
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Textbook Question
Sodium triacetoxyborohydride, NaBH(OAc)3, is a mild reducing agent that reduces aldehydes much more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones, such as in the following reaction:
(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.
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Textbook Question
Predict the products of the following reactions:
(c)
(d)
2
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Textbook Question
Predict the products of the following reactions:
(a)
(b)
2
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