Textbook Question
Compare the properties of propan-2-ol (I) and the hexafluoro analog (II).
(a) Compound II has almost triple the molecular weight of I, but II has a lower boiling point. Explain.
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 52c
Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.
c. 1-(hydroxymethyl)cyclohexanol
Verified step by step guidance1
Step 1: Begin with methylenecyclohexane as the starting material. Perform a hydroboration-oxidation reaction to convert the double bond into an alcohol group. Use BH₃·THF (borane in tetrahydrofuran) for hydroboration, followed by oxidation with H₂O₂ (hydrogen peroxide) in a basic solution (NaOH). This will yield cyclohexanol.
Step 2: To introduce the hydroxymethyl group, use formaldehyde (HCHO) as the reagent. React cyclohexanol with formaldehyde in the presence of an acid catalyst (e.g., HCl or H₂SO₄) to perform a hydroxymethylation reaction. This will attach a hydroxymethyl group (-CH₂OH) to the cyclohexanol.
Step 3: Ensure the reaction conditions are controlled to avoid overreaction or polymerization of formaldehyde. Monitor the reaction to confirm the formation of 1-(hydroxymethyl)cyclohexanol.
Step 4: Purify the product using techniques such as distillation or recrystallization, depending on the physical properties of the compound. This step ensures the removal of any unreacted starting materials or by-products.
Step 5: Confirm the structure of the synthesized compound using spectroscopic methods such as NMR (nuclear magnetic resonance) and IR (infrared spectroscopy). Look for characteristic peaks corresponding to the hydroxyl (-OH) and hydroxymethyl (-CH₂OH) groups.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Synthesis in Organic Chemistry
Synthesis in organic chemistry refers to the process of constructing complex organic compounds from simpler ones through a series of chemical reactions. Understanding the target compound's structure and functional groups is crucial for determining the appropriate reagents and reaction conditions needed to achieve the desired transformation.
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What is an organic molecule?
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the case of 1-(hydroxymethyl)cyclohexanol, the hydroxymethyl (-CH2OH) group is essential for understanding how to manipulate the starting material, methylenecyclohexane, to introduce this functional group through various reactions.
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Reagents and Reaction Mechanisms
Reagents are substances used to bring about a chemical reaction, and understanding their roles is vital for successful synthesis. Different reagents can facilitate various reaction mechanisms, such as nucleophilic substitution or electrophilic addition, which are key to transforming methylenecyclohexane into 1-(hydroxymethyl)cyclohexanol by adding the hydroxymethyl group effectively.
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Related Practice
Textbook Question
Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.
f. 1-(phenylmethyl)cyclohexanol
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Textbook Question
Propose structures for intermediates and products (F) through (G)
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Textbook Question
Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.
a. 1-methylcyclohexanol
Textbook Question
Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.
b. cyclohexylmethanol
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Textbook Question
Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.
d. trans-2-methylcyclohexanol
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