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Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:
f.
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Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 62c
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 62cCapitolo 16, Problema 62c
Show how each of the following compounds can be prepared, using the given starting material:
c. 
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Step 1: Analyze the starting material and the target compound. The starting material is cyclopentanol (a cyclic alcohol), and the target compound is N-ethylcyclopentylamine (a cyclic amine with an ethyl group attached to the nitrogen). This indicates that the hydroxyl group (-OH) must be replaced with an amine group (-NH2), followed by alkylation to introduce the ethyl group.
Step 2: Convert the alcohol group (-OH) into a good leaving group. This can be achieved by reacting cyclopentanol with a reagent like thionyl chloride (SOCl₂) or phosphorus tribromide (PBr₃) to form cyclopentyl chloride (a cyclic alkyl halide). This step ensures the hydroxyl group is replaced with a halide, which is more reactive for substitution reactions.
Step 3: Perform nucleophilic substitution to replace the halide group with an amine group (-NH2). React cyclopentyl chloride with ammonia (NH₃) under appropriate conditions to yield cyclopentylamine. This step introduces the amine functionality into the molecule.
Step 4: Alkylate the amine group to introduce the ethyl group. React cyclopentylamine with ethyl bromide (C₂H₅Br) or ethyl iodide (C₂H₅I) in the presence of a base like potassium carbonate (K₂CO₃). This step results in the formation of N-ethylcyclopentylamine.
Step 5: Purify the product using techniques such as distillation or recrystallization, depending on the physical properties of N-ethylcyclopentylamine, to ensure the final compound is free of impurities.
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Alcohol to Amine Conversion
The conversion of an alcohol to an amine typically involves the substitution of the hydroxyl (-OH) group with an amine (-NH2) group. This can be achieved through various methods, such as using reagents like thionyl chloride (SOCl2) to convert the alcohol into a better leaving group, followed by nucleophilic substitution with ammonia or an amine.
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Nucleophilic Substitution Reactions
Nucleophilic substitution reactions are fundamental in organic chemistry, where a nucleophile attacks an electrophilic carbon atom, replacing a leaving group. In the context of alcohols, the hydroxyl group is a poor leaving group, so it is often converted into a better leaving group to facilitate the reaction with nucleophiles like amines.
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Reactivity of Alcohols
Alcohols are versatile compounds in organic synthesis, but their reactivity depends on the structure and the presence of functional groups. Primary alcohols can be converted to amines more readily than tertiary alcohols due to steric hindrance and the stability of the resulting carbocation during the reaction process.
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