Textbook Question
Using any necessary reagents, show how you would accomplish the following syntheses.
(b)
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Ch. 19 - Amines
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 19, Problem 42e,f
Using any necessary reagents, show how you would accomplish the following syntheses.
(e) 
(f) 
Verified step by step guidance1
Step 1: For reaction (a), identify the starting material as an ethylamine derivative of cyclohexane and the product as a quaternary ammonium salt. This suggests the reaction involves alkylation of the amine group.
Step 2: To achieve the transformation in (a), use an alkyl halide such as ethyl bromide (CH3CH2Br) as the reagent. The nitrogen atom in the amine group will act as a nucleophile and attack the alkyl halide, forming the quaternary ammonium salt.
Step 3: For reaction (b), identify the starting material as the same ethylamine derivative of cyclohexane and the product as a compound with an extended carbon chain containing a hydroxyl group and a double bond.
Step 4: To accomplish the transformation in (b), use a sequence of reactions. First, perform an alkylation reaction to introduce the extended carbon chain using an alkyl halide such as 1-bromohexane. Then, oxidize the terminal carbon to introduce the hydroxyl group using an oxidizing agent like PCC (Pyridinium Chlorochromate).
Step 5: Finally, introduce the double bond in the extended chain by performing an elimination reaction using a base such as NaOH or KOH. This will remove a hydrogen atom and a leaving group, forming the double bond in the desired position.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Cope Elimination
Cope elimination is a reaction mechanism involving the removal of a leaving group and a hydrogen atom from adjacent carbon atoms, resulting in the formation of an alkene. This process typically occurs in the presence of a base and is characterized by a concerted mechanism, where bond breaking and forming happen simultaneously. Understanding this mechanism is crucial for predicting the products of reactions involving amines and cyclic compounds.
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Definition of Cope Rearrangement
Amines and Their Reactivity
Amines are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. Their reactivity is influenced by the presence of the nitrogen atom, which can act as a nucleophile or a base. In synthetic organic chemistry, amines can undergo various transformations, including alkylation and acylation, making them versatile intermediates in the synthesis of more complex molecules.
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Reaction Mechanisms
Understanding reaction mechanisms is essential in organic chemistry as it provides insight into how reactants transform into products. Mechanisms detail the step-by-step process of a reaction, including the formation and breaking of bonds, the role of catalysts, and the energy changes involved. This knowledge allows chemists to predict reaction outcomes and design synthetic pathways effectively, particularly in complex reactions like those involving amines.
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Related Practice
Textbook Question
The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.
(b) Methamphetamine, once considered a safe diet pill, but now known to be addictive and destructive to brain tissue.
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Textbook Question
The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.
(a) Phenacetin, used with aspirin and caffeine in pain-relief medications.
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Textbook Question
Using any necessary reagents, show how you would accomplish the following syntheses.
(g)
1133
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Textbook Question
Using any necessary reagents, show how you would accomplish the following syntheses.
(c)
1232
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Textbook Question
Using any necessary reagents, show how you would accomplish the following syntheses.
(d)
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