Textbook Question
Show how this 1° alcohol can be made from the following:
(c) a 7-carbon aldehyde
(d) a carboxylic acid
854
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Ch.10 - Structure and Synthesis 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 10, Problem 58b
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.
(b) 
Verified step by step guidance1
Step 1: Analyze the first reaction. Bromocyclohexane reacts with KOH in ethanol under heat (Δ). This is an elimination reaction 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 (compound A) reacts with KMnO4 in NaOH under heat (Δ). This is an oxidative cleavage reaction where the double bond in cyclohexene is broken, forming a dicarboxylic acid (compound E).
Step 3: Consider the third reaction. The dicarboxylic acid (compound E) is treated with LiAlH4 in ether. LiAlH4 is a strong reducing agent that reduces carboxylic acids to primary alcohols, resulting in a diol (compound F).
Step 4: The final step involves the diol (compound F) being treated with dilute H3O+. This step ensures the reaction is complete and neutralizes any remaining basic conditions from the previous step.
Step 5: Summarize the transformations. Bromocyclohexane undergoes elimination to form cyclohexene, oxidative cleavage to form a dicarboxylic acid, and reduction to form a diol, followed by neutralization.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, bromocyclohexane undergoes nucleophilic substitution with KOH in ethanol, leading to the formation of an alcohol. Understanding this mechanism is crucial for predicting the products of the reaction and the subsequent steps in the synthesis.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Oxidation Reactions
Oxidation reactions involve the increase of oxidation state of a molecule, often through the addition of oxygen or the removal of hydrogen. In the provided synthesis, the intermediate A is oxidized using KMnO4 in a basic medium, which typically converts alcohols to carbonyl compounds or carboxylic acids. Recognizing the role of oxidizing agents is essential for predicting the transformation of intermediates in organic synthesis.
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Reduction Reactions
Reduction reactions are processes that decrease the oxidation state of a molecule, often involving the addition of hydrogen or the removal of oxygen. In this synthesis, LiAlH4 is used to reduce the carbonyl compound E to an alcohol F. Understanding reduction mechanisms is vital for determining how functional groups can be transformed in organic synthesis.
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Related Practice
Textbook Question
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.
(c)
899
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Textbook Question
Problem 8-54 describes a new method to perform ozonolysis reactions that used pyridine (py) to generate the final aldehydes and ketones in a non-aqueous reaction medium. In a subsequent publication (J. Org. Chem., 2013, 78, 42), Professor Dussault (U. of Nebraska at Lincoln) described a “tandem” process in which two reactions are performed sequentially without having to isolate the intermediate aldehyde or ketone. Show the final product from each sequence. (Hint: The isolated products were from the larger part of the structure. Ignore stereochemistry.)
(c)
(d)
849
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Textbook Question
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)
1630
views
Textbook Question
Problem 8-54 describes a new method to perform ozonolysis reactions that used pyridine (py) to generate the final aldehydes and ketones in a non-aqueous reaction medium. In a subsequent publication (J. Org. Chem., 2013, 78, 42), Professor Dussault (U. of Nebraska at Lincoln) described a “tandem” process in which two reactions are performed sequentially without having to isolate the intermediate aldehyde or ketone. Show the final product from each sequence. (Hint: The isolated products were from the larger part of the structure. Ignore stereochemistry.)
(a)
(b)
1017
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Textbook Question
Show how this 1° alcohol can be made from the following:
(e) an alkene
(f) ethylene oxide
863
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