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 54a
Compounds containing deuterium (D = 2H) are useful for kinetic studies and metabolic studies with new pharmaceuticals. One way to introduce deuterium is by using the reagent LiAlD4, equivalent in reactivity to LiAlH4. Show how to make these deuterium-labeled compounds, using LiAlD4 and D2O as your sources of deuterium, and any non-deuterated starting materials you wish.
a. CH3CHDOH
Verified step by step guidance1
Step 1: Understand the problem. The goal is to synthesize CH3CHDOH, which is ethanol with one hydrogen replaced by deuterium (D). The reagent LiAlD4 is a deuterium-labeled reducing agent, and D2O is heavy water, both of which can introduce deuterium into the molecule.
Step 2: Select a suitable non-deuterated starting material. A good choice would be acetaldehyde (CH3CHO), as it can be reduced to ethanol using LiAlH4 or LiAlD4.
Step 3: Use LiAlD4 as the reducing agent. React acetaldehyde (CH3CHO) with LiAlD4. The hydride (H-) in LiAlH4 is replaced by deuteride (D-), so the reduction will introduce deuterium into the molecule, forming CH3CHDOH.
Step 4: Consider the role of D2O. If additional deuterium incorporation is needed, D2O can be used as a solvent or reactant to exchange labile hydrogens with deuterium. However, in this case, the reduction with LiAlD4 is sufficient to introduce the desired deuterium.
Step 5: Verify the product. After the reaction, confirm the structure of CH3CHDOH using spectroscopic techniques such as NMR, which can distinguish between hydrogen and deuterium atoms based on their different nuclear properties.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Deuterium and Its Applications
Deuterium is a stable isotope of hydrogen, represented as D or 2H, which contains one proton and one neutron. Its unique properties make it valuable in kinetic and metabolic studies, particularly in pharmaceuticals, as it can help trace reaction pathways and metabolic processes without altering the chemical behavior of the compounds.
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Understanding the hydrogen isotopes.
Lithium Aluminum Deuteride (LiAlD4)
LiAlD4 is a powerful reducing agent similar to LiAlH4 but contains deuterium instead of hydrogen. It is used to introduce deuterium into organic compounds through reduction reactions, allowing for the synthesis of deuterium-labeled compounds, which are essential for studying reaction mechanisms and metabolic pathways.
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Deuteration Reaction Mechanism
The deuteration reaction mechanism involves the substitution of hydrogen atoms in organic compounds with deuterium atoms. In the case of synthesizing CH3CHDOH, the reaction with LiAlD4 and D2O facilitates the transfer of deuterium to the hydroxyl group, resulting in the formation of a deuterated alcohol. Understanding this mechanism is crucial for predicting the outcomes of reactions involving deuterated reagents.
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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
1
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Textbook Question
Compounds containing deuterium (D = 2H) are useful for kinetic studies and metabolic studies with new pharmaceuticals. One way to introduce deuterium is by using the reagent LiAlD4, equivalent in reactivity to LiAlH4. Show how to make these deuterium-labeled compounds, using LiAlD4 and D2O as your sources of deuterium, and any non-deuterated starting materials you wish.
(b) CH3CD2OH
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Textbook Question
Show how to make these deuterium-labeled compounds, using CD3MgBr and D2O as your sources of deuterium, and any non-deuterated starting materials you wish.
a. CH3CH(OD)CD3
1
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Textbook Question
Compounds containing deuterium (D = 2H) are useful for kinetic studies and metabolic studies with new pharmaceuticals. One way to introduce deuterium is by using the reagent LiAlD4, equivalent in reactivity to LiAlH4. Show how to make these deuterium-labeled compounds, using LiAlD4 and D2O as your sources of deuterium, and any non-deuterated starting materials you wish.
(c) CH3CD2OD
2
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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
1
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