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 54b
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
Verified step by step guidance1
Step 1: Understand the problem. The goal is to synthesize CH3CD2OH, a deuterium-labeled alcohol, using LiAlD4 and D2O as sources of deuterium. LiAlD4 is a reducing agent that introduces deuterium (D) in place of hydrogen (H), and D2O can be used to exchange hydrogen atoms with deuterium.
Step 2: Select a suitable non-deuterated starting material. For this synthesis, you can start with CH3CHO (acetaldehyde), which contains a carbonyl group that can be reduced to an alcohol.
Step 3: Use LiAlD4 to reduce the carbonyl group in CH3CHO. The hydride (H-) equivalent in LiAlD4 is replaced by deuteride (D-), so the reduction will introduce deuterium atoms into the molecule. The reaction will convert CH3CHO into CH3CD2OH.
Step 4: If additional deuterium incorporation is needed, treat the product (CH3CD2OH) with D2O under acidic or basic conditions. This step allows for exchange of any remaining hydrogen atoms with deuterium from D2O.
Step 5: Verify the structure of the final product, CH3CD2OH, ensuring that the deuterium atoms are correctly incorporated at the desired positions. This can be confirmed using spectroscopic techniques such as NMR (nuclear magnetic resonance).
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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 specifically used for introducing deuterium into organic compounds. It reacts with various functional groups, facilitating the substitution of hydrogen atoms with deuterium, which is essential for synthesizing deuterium-labeled compounds for research purposes.
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Deuterated Alcohol Synthesis
The synthesis of deuterated alcohols, such as CH3CD2OH, involves the reaction of non-deuterated starting materials with deuterium sources like LiAlD4 and D2O. This process typically includes reduction reactions where deuterium replaces hydrogen in the alcohol structure, allowing for the creation of compounds that can be used in various analytical studies.
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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
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
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.
b. CH3C(OH)(CD3)2
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.
a. CH3CHDOH
2
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