Textbook Question
Show how you would make each compound, beginning with an alcohol of your choice.
(d)
(e)
(f)
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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 48g,h
Show how you would make each compound, beginning with an alcohol of your choice.
(g) 
(h) 
Verified step by step guidance1
Step 1: For compound (g), identify the target molecule as a ketone with a cyclohexane ring and a tertiary butyl group attached. To synthesize this compound, start with an alcohol that can be oxidized to the ketone. Choose an alcohol such as 1-tert-butylcyclohexanol.
Step 2: Perform an oxidation reaction to convert the alcohol to the ketone. Use an oxidizing agent such as PCC (Pyridinium Chlorochromate) or Jones reagent (CrO3/H2SO4) under controlled conditions to avoid overoxidation.
Step 3: For compound (h), identify the target molecule as a cyclohexane ring with a methyl group and a tosylate group in a trans configuration. Start with an alcohol that can be converted to the tosylate. Choose an alcohol such as trans-2-methylcyclohexanol.
Step 4: Convert the alcohol to the tosylate by reacting it with p-toluenesulfonyl chloride (TsCl) in the presence of a base such as pyridine. This reaction replaces the hydroxyl group with the tosylate group.
Step 5: Ensure stereochemistry is preserved during the tosylation reaction. Verify that the trans configuration of the methyl and tosylate groups is maintained in the final product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alcohols as Starting Materials
Alcohols are organic compounds containing one or more hydroxyl (-OH) groups. They serve as versatile starting materials in organic synthesis due to their ability to undergo various reactions, such as oxidation, substitution, and dehydration. Understanding the structure and reactivity of alcohols is crucial for planning synthetic pathways to target compounds.
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How to name alcohols
Functional Group Transformations
Functional group transformations involve converting one functional group into another through chemical reactions. This concept is essential in organic synthesis, as it allows chemists to modify the structure of a compound to achieve desired properties or reactivity. Familiarity with common transformations, such as converting alcohols to aldehydes or ketones, is vital for constructing complex molecules.
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Reaction Mechanisms
Understanding reaction mechanisms is key to predicting the outcomes of chemical reactions. A mechanism outlines the step-by-step process by which reactants are converted into products, including the formation and breaking of bonds. Knowledge of mechanisms helps chemists design efficient synthetic routes and anticipate potential side reactions when synthesizing compounds from alcohols.
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Related Practice
Textbook Question
Show how you would convert (S)-hexan-2-ol to
(a) (S)-2-chlorohexane.
(b) (R)-2-bromohexane.
(c) (R)-hexan-2-ol.
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Textbook Question
Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation using TsCl and pyridine, followed by elimination using KOC(CH3)3 as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanol eliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.
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Textbook Question
Predict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents.
(a) PBr3
(b) SOCl2
(c) Lucas reagent
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Textbook Question
Predict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents.
(d) concentrated HBr
(e) TsCl/pyridine, then NaBr
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Textbook Question
The compound shown below has three different types of OH groups, all with different acidities. Show the structure produced after this compound is treated with different amounts of NaH followed by a methylating reagent. Add a brief explanation.
(a) 1 equivalent of NaH, followed by 1 equivalent of CH3I and heat
(b) 2 equivalents of NaH, followed by 2 equivalents of CH3I and heat
(c) 3 equivalents of NaH, followed by 3 equivalents of CH3I and heat
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