Textbook Question
Propose mechanisms for the following reactions. In most cases, more products are formed than are shown here. You only need to explain the formation of the products shown, however.
(b)
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Ch.11 - Reactions of Alcohols
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 11, Problem 56g
Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.
(g) 
Verified step by step guidance1
Step 1: Analyze the target molecule. The compound contains a nitrile group (-C≡N) attached to a carbon atom that is also bonded to a hydrogen atom, a methyl group (-CH3), and an ethyl group (-CH2CH3). This suggests that the synthesis involves forming a nitrile group and constructing the correct carbon framework.
Step 2: Start with a suitable alcohol as the starting material. Since alcohols with four or fewer carbon atoms are allowed, choose 2-butanol (CH3CH(OH)CH2CH3) as the starting material. This alcohol has the correct carbon framework to form the desired product.
Step 3: Convert the alcohol to a halide. Use a reagent like thionyl chloride (SOCl2) or phosphorus tribromide (PBr3) to convert 2-butanol into 2-bromobutane (CH3CH(Br)CH2CH3). This step introduces a good leaving group for subsequent reactions.
Step 4: Perform a nucleophilic substitution reaction to introduce the nitrile group. React 2-bromobutane with sodium cyanide (NaCN) in an appropriate solvent like dimethyl sulfoxide (DMSO). This reaction replaces the bromine atom with a nitrile group, forming 2-butanenitrile (CH3CH(C≡N)CH2CH3).
Step 5: Ensure stereochemistry. If the target molecule requires a specific stereochemistry (e.g., the hydrogen and nitrile group are on opposite sides of the carbon atom), use appropriate conditions or reagents to control the stereochemistry during the substitution step. Verify the stereochemistry of the product using spectroscopic methods like NMR.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alcohols as Reactants
Alcohols are organic compounds containing one or more hydroxyl (-OH) groups. In synthesis, they can act as nucleophiles or electrophiles depending on the reaction conditions. Understanding the reactivity of different alcohols, especially those with four or fewer carbon atoms, is crucial for designing synthetic pathways to target compounds.
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How to name alcohols
Functional Group Transformations
Functional group transformations involve converting one functional group into another through various chemical reactions. This concept is essential in organic synthesis, as it allows chemists to modify the structure of starting materials to create desired products. Familiarity with common transformations, such as oxidation, reduction, and substitution, is vital for effective synthesis.
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02:36Identifying Functional Groups
Reagents and Solvents in Organic Synthesis
Reagents and solvents play a critical role in organic synthesis by influencing reaction mechanisms and outcomes. In this context, inorganic reagents may be used to facilitate transformations, while solvents can affect solubility and reaction rates. Understanding the properties and roles of different reagents and solvents is essential for optimizing synthetic routes.
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01:16Identification of polarity in solvents
Related Practice
Textbook Question
Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.
(h)
897
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Textbook Question
Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.
(a)
(b)
(c)
1583
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Textbook Question
Show how you would synthesize the following compound. As starting materials, you may use any alcohols containing five or fewer carbon atoms and any necessary solvents and inorganic reagents.
964
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Textbook Question
Propose mechanisms for the following reactions. In most cases, more products are formed than are shown here. You only need to explain the formation of the products shown, however.
(c)
588
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Textbook Question
The following pseudo-syntheses (guaranteed not to work) exemplify a common conceptual error.
(a) What is the conceptual error implicit in these syntheses?
(b) Propose syntheses that are more likely to succeed.
766
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