Domanda del libro di testo
Show how this 1° alcohol can be made from the following:
(c) a 7-carbon aldehyde
(d) a carboxylic acid
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Ch.10 - Structure and Synthesis of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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TOC.tableOfContents
- 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
Capitolo 10, Problema 58a
For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.
(a) 
Guida verificata passo dopo passo1
Step 1: Analyze the first reaction. Bromocyclohexane reacts with KOH in ethanol under heat (Δ). This is an elimination reaction (E2 mechanism), where the bromine atom is removed, and a double bond is formed in the cyclohexane ring, resulting in cyclohexene (compound A).
Step 2: Examine the second reaction. Cyclohexene undergoes ozonolysis with ozone (O₃) at -78°C, followed by reduction with dimethyl sulfide (Me₂S) and water. This cleaves the double bond in cyclohexene, producing two carbonyl compounds (aldehydes or ketones, depending on the structure). These products are compound B.
Step 3: Consider the third reaction. One of the carbonyl compounds from the ozonolysis step reacts with ethylmagnesium bromide (Grignard reagent) to form an alcohol. The Grignard reagent adds to the carbonyl group, creating a new C-C bond.
Step 4: The reaction is completed by hydrolysis with H₃O⁺, which protonates the intermediate formed in the Grignard reaction, yielding the final alcohol product (compound C).
Step 5: Summarize the transformations. Bromocyclohexane undergoes elimination to form cyclohexene, ozonolysis to produce carbonyl compounds, and finally Grignard addition followed by hydrolysis to yield the alcohol product.
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Elimination Reactions
Elimination reactions involve the removal of a small molecule from a larger one, resulting in the formation of a double bond. In this synthesis, the treatment of bromocyclohexane with KOH in ethanol leads to the formation of an alkene through an E2 elimination mechanism. Understanding the conditions and mechanisms of elimination reactions is crucial for predicting the formation of product A.
Video consigliato:
00:40
Recognizing Elimination Reactions.
Ozonolysis
Ozonolysis is a reaction where alkenes are cleaved by ozone (O3) to form carbonyl compounds. In the synthesis, product A undergoes ozonolysis followed by workup with dimethyl sulfide and water to yield product B. This reaction is significant for understanding how to manipulate alkenes to create specific carbonyl-containing products.
Video consigliato:
06:30General properties of ozonolysis.
Grignard Reagents
Grignard reagents are organomagnesium compounds that react with carbonyls to form alcohols. In this synthesis, product B reacts with a Grignard reagent (MgBr) to produce product C after hydrolysis. Knowledge of Grignard chemistry is essential for predicting the final product and understanding the reactivity of carbonyl compounds in organic synthesis.
Video consigliato:
02:12Carbonation of Grignard Reagents
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For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.
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