Textbook Question
Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.
(a) cyclopentyl n-propyl ether from cyclopentanol and propan-1-ol
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Ch. 14 - Ethers, Epoxides, and Thioethers
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 14, Problem 43b
Give the structures of the intermediates represented by letters K and Q in this synthesis.
Verified step by step guidance1
Step 1: Analyze the starting material, which is an ester (phenylpropanoate). The first reaction involves LiAlH4 in ether followed by H3O+. This is a reduction reaction that converts the ester into a primary alcohol. The intermediate labeled 'J' is the primary alcohol formed from the reduction of the ester.
Step 2: The alcohol 'J' is treated with TsCl (tosyl chloride) in pyridine. This reaction converts the alcohol into a tosylate, which is a good leaving group. The intermediate labeled 'L' is the tosylate derivative of the alcohol.
Step 3: The tosylate 'L' undergoes elimination with KO-tBu (potassium tert-butoxide), a strong base. This results in the formation of an alkene via an E2 elimination mechanism. The intermediate labeled 'M' is the alkene formed.
Step 4: The alkene 'M' is treated with Br2 followed by H2O. This is a halohydrin formation reaction, where bromine adds across the double bond and water attacks the more substituted carbon. The intermediate labeled 'N' is the halohydrin formed.
Step 5: The halohydrin 'N' is treated with TIPS-Cl (triisopropylsilyl chloride) and Et3N (triethylamine). This reaction protects the hydroxyl group by converting it into a silyl ether. The intermediate labeled 'O' is the silyl-protected halohydrin.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Synthesis Pathways
Synthesis pathways illustrate the step-by-step transformation of reactants into products through various intermediates. Understanding these pathways is crucial for predicting the structure of intermediates, as each step often involves specific reagents and conditions that dictate the outcome of the reaction. Familiarity with common reactions, such as reductions, oxidations, and substitutions, is essential for interpreting the diagram and identifying the intermediates labeled A to Q.
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Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In organic synthesis, recognizing functional groups such as alcohols, aldehydes, ketones, and ethers is vital for understanding how intermediates will behave during reactions. The presence of these groups influences reactivity and the types of transformations that can occur, which is key to deducing the structures of intermediates in the synthesis pathway.
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Reagents and Conditions
The choice of reagents and reaction conditions significantly affects the course of a chemical reaction and the formation of intermediates. For example, reagents like LiAlH4 are strong reducing agents, while TsCl is used for activating alcohols for substitution reactions. Understanding the role of each reagent and the conditions under which they operate helps in predicting the structures of intermediates and the overall success of the synthesis process.
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Related Practice
Textbook Question
Both LiAlH4 and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that become protonated in an aqueous workup). Those alkoxides can react with 1° or methyl alkyl halides or tosylates to give ethers. Show how the following ethers can be formed in this two-step process. As starting materials you may use any reactants containing 7 carbons or fewer.
(c)
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Textbook Question
Give the structures of the intermediates represented by letters O, P, and Q in this synthesis.
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Textbook Question
Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.
(b) n-butyl phenyl ether from phenol and butan-1-ol
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Textbook Question
Give the structures of intermediates A through H in the following synthesis of trans-1-cyclohexyl-2-methoxycyclohexane.
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Textbook Question
Give the structures of the intermediates represented by letters J, L, M, and N in this synthesis.
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