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 21c
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
Verified step by step guidance1
Step 1: Identify the target molecule, trans-oct-3-ene. This is an alkene with a trans configuration, meaning the two substituents on the double bond are on opposite sides. The double bond is located between carbons 3 and 4 in an 8-carbon chain.
Step 2: Plan the retrosynthesis. Break the molecule into smaller components that can be synthesized from the allowed starting materials (alkyl halides, vinyl halides, and aryl halides with no more than six carbons). A logical disconnection is at the double bond, suggesting a coupling reaction such as the Wittig reaction or a cross-coupling reaction like the Heck reaction.
Step 3: Choose a suitable reaction. For this synthesis, the Heck reaction is a good choice. The Heck reaction involves the coupling of a vinyl halide with an alkyl halide in the presence of a palladium catalyst to form a substituted alkene. Ensure that the starting materials are trans-configured to maintain the stereochemistry of the product.
Step 4: Select the starting materials. Use a vinyl halide such as 1-bromo-1-hexene (C6H11Br) and an alkyl halide such as ethyl bromide (C2H5Br). These compounds meet the requirement of having no more than six carbons.
Step 5: Perform the Heck reaction. Combine the vinyl halide and alkyl halide in the presence of a palladium catalyst (e.g., Pd(PPh3)4) and a base (e.g., triethylamine) under appropriate reaction conditions. This will yield trans-oct-3-ene as the product.
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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 that contain one or more halogen atoms (F, Cl, Br, I) attached to a carbon atom. They are key intermediates in organic synthesis, often undergoing nucleophilic substitution or elimination reactions to form alkenes or other functional groups. Understanding their reactivity is essential for synthesizing compounds like trans-oct-3-ene.
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Elimination Reactions
Elimination reactions involve the removal of a small molecule (often HX) from a larger molecule, resulting in the formation of a double bond. In the context of synthesizing alkenes, such as trans-oct-3-ene, elimination can be achieved through dehydrohalogenation of alkyl halides. The stereochemistry of the elimination reaction is crucial for obtaining the desired trans isomer.
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Stereochemistry
Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical properties and reactions. For trans-oct-3-ene, the specific arrangement of substituents around the double bond is important for its identity and reactivity. Understanding stereochemical principles helps in predicting the outcomes of reactions and ensuring the correct isomer is synthesized.
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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
Predict the products of the following reactions.
(d)
(e)
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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.
(a) octane
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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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