Textbook Question
Show how you would convert propan-1-ol to the following compounds using tosylate intermediates. You may use whatever additional reagents are needed.
c. CH3CH2CH2OCH2CH3, ethyl proyl ether
d. CH3CH2CH2CN, butyronitrile
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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 10a,b
Show how you would convert propan-1-ol to the following compounds using tosylate intermediates. You may use whatever additional reagents are needed.
a. 1-bromopropane
b. propan-1-amine, CH3CH2CH2NH2
Verified step by step guidance1
Step 1: Begin by converting propan-1-ol (CH3CH2CH2OH) into its tosylate intermediate. This is achieved by reacting propan-1-ol with p-toluenesulfonyl chloride (TsCl) in the presence of a base such as pyridine. The hydroxyl group (-OH) is replaced with a tosyl group (-OTs), forming propyl tosylate (CH3CH2CH2OTs).
Step 2: For part (a), to convert propyl tosylate into 1-bromopropane (CH3CH2CH2Br), perform a nucleophilic substitution reaction. React propyl tosylate with sodium bromide (NaBr) in a polar aprotic solvent like acetone. The tosyl group (-OTs) is replaced by a bromide ion (Br⁻) via an SN2 mechanism.
Step 3: For part (b), to convert propyl tosylate into propan-1-amine (CH3CH2CH2NH2), perform another nucleophilic substitution reaction. React propyl tosylate with excess ammonia (NH3) in a suitable solvent. The tosyl group (-OTs) is replaced by an amine group (-NH2) via an SN2 mechanism.
Step 4: Ensure proper reaction conditions for both conversions. For the SN2 reactions, use polar aprotic solvents to favor the substitution mechanism and avoid side reactions. Maintain appropriate temperatures to optimize reaction rates.
Step 5: After the reactions, purify the products (1-bromopropane and propan-1-amine) using techniques such as distillation or recrystallization, depending on the physical properties of the compounds. Confirm the identity of the products using spectroscopic methods like NMR or IR.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Tosylate Formation
Tosylates are formed by reacting alcohols with tosyl chloride (TsCl) in the presence of a base. This reaction converts the alcohol into a better leaving group, the tosylate, which can facilitate subsequent nucleophilic substitution reactions. The tosylate retains the configuration of the original alcohol, making it a useful intermediate for further transformations.
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Formation of Enolates
Nucleophilic Substitution Reactions
Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule with a nucleophile. In the case of converting tosylates, the nucleophile attacks the carbon atom bonded to the tosylate, leading to the formation of a new compound. This mechanism can follow either an SN1 or SN2 pathway, depending on the structure of the substrate and the nucleophile used.
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Reagents for Halogenation and Amination
To convert a tosylate to a bromo compound, reagents like sodium bromide (NaBr) in a polar aprotic solvent can be used to facilitate the substitution. For amination, a strong nucleophile such as ammonia (NH3) or an amine can be employed to replace the tosylate with an amine group. Understanding the choice of reagents is crucial for achieving the desired product efficiently.
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Related Practice
Textbook Question
A chronic alcoholic requires a much larger dose of ethanol as an antidote to methanol poisoning than does a nonalcoholic patient. Suggest a reason why a larger dose of the competitive inhibitor is required for an alcoholic.
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Textbook Question
Predict the major products of the following reactions.
(d) the tosylate of cyclohexylmethanol + excess NH3
(e) n-butyl tosylate + sodium acetylide, H–C≡C:– +Na
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Textbook Question
Predict the products of the following reactions.
(c) 1-methylcyclohexanol + H2SO4, heat
(d) product of (c) + H2, Pt
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Textbook Question
Predict the products of the following reactions.
(a) cyclohexylmethanol + TsCl/pyridine
(b) product of (a) + LiAlH4
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Textbook Question
Predict the major products of the following reactions.
(a) ethyl tosylate + potassium tert-butoxide
(b) isobutyl tosylate + NaI
(c) (R)-2-hexyl tosylate + NaCN
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