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.
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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 54c
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
Verified step by step guidance1
Step 1: Understand the problem. The goal is to synthesize CH3CD2OD, a deuterium-labeled compound, using LiAlD4 and D2O as sources of deuterium. LiAlD4 is a reducing agent that introduces deuterium (D) in place of hydrogen (H). D2O is heavy water, which can also provide deuterium atoms.
Step 2: Select a suitable non-deuterated starting material. For this synthesis, CH3CHO (acetaldehyde) is a good choice because it contains a carbonyl group that can be reduced by LiAlD4.
Step 3: Perform the reduction of CH3CHO using LiAlD4. The hydride-like deuterium from LiAlD4 will reduce the carbonyl group to form CH3CD2OH. This step involves nucleophilic attack of the deuterium on the carbonyl carbon, followed by protonation.
Step 4: Exchange the hydroxyl hydrogen in CH3CD2OH with deuterium using D2O. This can be achieved by treating CH3CD2OH with D2O under acidic or basic conditions, allowing the hydroxyl hydrogen to be replaced by deuterium, forming CH3CD2OD.
Step 5: Verify the structure of the final product, CH3CD2OD, ensuring that the deuterium atoms are correctly incorporated at the desired positions. This can be confirmed using spectroscopic techniques such as NMR or IR.
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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, containing 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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03:06
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 deuterated compounds, which are essential for studying reaction mechanisms and dynamics in organic chemistry.
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Deuterated Alcohol Synthesis
The synthesis of deuterated alcohols, such as CH3CD2OD, involves the reaction of non-deuterated starting materials with deuterium sources like LiAlD4 and D2O. This process typically includes reduction steps where the deuterium replaces hydrogen atoms, resulting in the formation of deuterated products that can be used in various analytical and experimental applications.
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Related Practice
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.
c. CD3CH2CH2OH
719
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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
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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.
b. CH3C(OH)(CD3)2
1653
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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
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