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 11b
Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.
(b) 
Verified step by step guidance1
Step 1: Analyze the target transformation. The starting material is benzophenone (Ph-C=O-Ph), and the product is triphenylmethanol (Ph3C-OH). This indicates the addition of a phenyl group to the carbonyl carbon and reduction of the carbonyl group to an alcohol.
Step 2: Use a Grignard reagent for the phenyl group addition. Prepare phenylmagnesium bromide (Ph-MgBr) by reacting bromobenzene (Ph-Br) with magnesium in dry ether. This reagent will act as a nucleophile.
Step 3: Perform the nucleophilic addition reaction. React benzophenone with phenylmagnesium bromide in an anhydrous solvent (e.g., diethyl ether). The Grignard reagent will attack the carbonyl carbon, forming a tertiary alkoxide intermediate.
Step 4: Protonate the alkoxide intermediate. Add a dilute acid (e.g., HCl or H2SO4) to the reaction mixture to protonate the alkoxide, converting it into the desired alcohol (triphenylmethanol).
Step 5: Purify the product. Isolate triphenylmethanol by extraction, followed by recrystallization or distillation to ensure purity.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reduction Reactions
Reduction reactions involve the gain of electrons or the addition of hydrogen to a molecule, often resulting in a decrease in oxidation state. In organic chemistry, common reducing agents include lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4), which can convert carbonyl compounds, like ketones and aldehydes, into alcohols.
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Reductive Amination
Carbonyl Compounds
Carbonyl compounds contain a carbon atom double-bonded to an oxygen atom (C=O). They are classified into aldehydes and ketones based on the carbonyl's position in the molecule. Understanding the reactivity of carbonyls is crucial, as they can undergo various reactions, including reduction to form alcohols, as illustrated in the given conversion.
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Nucleophilic Addition
Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, such as the carbon in a carbonyl group. This process is key in the conversion of carbonyl compounds to alcohols, as the nucleophile (often a hydride ion from a reducing agent) adds to the carbonyl carbon, leading to the formation of an alcohol.
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Related Practice
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:
(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride.
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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)
2
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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)
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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.
(a)
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