Textbook Question
Predict the products of the following reactions.
(a) sec-butylmagnesium iodide + D2O
(b) n-butyllithium + CH3CH2OH
(c) isobutylmagnesium bromide + but-1-yne
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Ch.10 - Structure and Synthesis 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 10, Problem 21a
Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.
(a) octane
Verified step by step guidance1
Identify the target molecule, octane, which is a straight-chain alkane with eight carbon atoms (C₈H₁₈). The goal is to construct this molecule using smaller alkyl halides, vinyl halides, or aryl halides containing no more than six carbon atoms.
Choose a synthetic strategy. Since octane is a simple alkane, a logical approach is to use a coupling reaction, such as the Wurtz reaction, which involves the coupling of two alkyl halides in the presence of sodium metal to form a longer alkane.
Select appropriate starting materials. To synthesize octane, you can use two alkyl halides with four carbon atoms each, such as 1-bromobutane (C₄H₉Br). This ensures that the total number of carbons in the product will be eight.
Write the reaction mechanism. In the Wurtz reaction, two molecules of 1-bromobutane react with sodium metal in a dry ether solvent. The sodium metal donates electrons to the alkyl halides, forming alkyl radicals, which then couple to form octane. The reaction can be represented as: .
Verify the product. After the reaction, confirm that the product is octane by analyzing its structure and ensuring it matches the target molecule. Additionally, ensure that no side reactions or byproducts interfere with the synthesis.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkyl Halides
Alkyl halides are organic compounds derived from alkanes by replacing one or more hydrogen atoms with halogen atoms (e.g., Cl, Br, I). They serve as important intermediates in organic synthesis, allowing for the formation of various functional groups through nucleophilic substitution or elimination reactions. Understanding their reactivity is crucial for designing synthetic pathways.
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Vinyl and Aryl Halides
Vinyl halides contain a halogen atom bonded to a carbon-carbon double bond, while aryl halides have a halogen atom attached to an aromatic ring. These compounds exhibit unique reactivity patterns due to the presence of π bonds or resonance stabilization, which can influence the types of reactions they undergo. Their roles in synthesis often involve coupling reactions or nucleophilic substitutions.
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Synthesis Strategies
Synthesis strategies in organic chemistry involve planning a series of chemical reactions to construct a target molecule from simpler precursors. Techniques such as chain elongation, functional group transformations, and coupling reactions are commonly employed. For synthesizing octane, one might consider using alkyl halides in nucleophilic substitution reactions or coupling reactions to build the carbon chain effectively.
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Related Practice
Textbook Question
Show how you would synthesize the following alcohol by adding Grignard reagents to ethylene oxide.
(c)
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Textbook Question
Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.
(c) trans-oct-3-ene
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Textbook Question
Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.
(d) cyclopentyl propyl ketone
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Textbook Question
Acetylide ions also add to ethylene oxide much like Grignard and organolithium reagents. Predict the products obtained by adding the following acetylide ions to ethylene oxide, followed by a dilute acid workup.
(a) HC≡C:–
(b) CH3CH2–C≡C:–
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Textbook Question
Show how you would synthesize the following alcohol by adding Grignard reagents to ethylene oxide.
(a) 2-phenylethanol