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
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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 55b
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
Verified step by step guidance1
Start with a non-deuterated ketone, such as acetone (CH3C(O)CH3), as your starting material. Acetone has a carbonyl group that can undergo nucleophilic addition reactions.
React acetone with CD3MgBr (a Grignard reagent containing deuterium). The nucleophilic CD3⁻ group will attack the electrophilic carbonyl carbon of acetone, forming a tetrahedral intermediate.
Protonate the tetrahedral intermediate by adding D2O (deuterium oxide). This step will replace the oxygen atom of the carbonyl group with an OD group, resulting in the formation of CH3C(OD)(CD3)2.
Recognize that the OD group can be converted to an OH group by exchanging the deuterium atom with a hydrogen atom. This can be achieved by treating the compound with a mild acidic or neutral aqueous solution.
The final product is CH3C(OH)(CD3)2, where the two CD3 groups are deuterium-labeled, and the hydroxyl group is non-deuterated.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Deuterium Labeling
Deuterium labeling involves substituting hydrogen atoms in organic compounds with deuterium, a stable isotope of hydrogen. This process is crucial in tracing the pathways of chemical reactions and understanding molecular structures. In this context, deuterium-labeled compounds can provide insights into reaction mechanisms and kinetics.
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Understanding the hydrogen isotopes.
Grignard Reagents
Grignard reagents, such as CD3MgBr, are organomagnesium compounds used in organic synthesis to form carbon-carbon bonds. They react with electrophiles, including carbonyl compounds, to create new carbon centers. Understanding how to utilize Grignard reagents is essential for constructing complex organic molecules, including those with deuterium labels.
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Alcohol Formation
The formation of alcohols from carbonyl compounds is a fundamental reaction in organic chemistry. In this case, the reaction of a Grignard reagent with a carbonyl compound leads to the formation of a tertiary alcohol. Recognizing the mechanisms of alcohol formation, including the role of deuterium in the final product, is vital for synthesizing the desired deuterium-labeled compound.
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Related Practice
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
1692
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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
636
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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.
d. Ph(CD3)2COD
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Textbook Question
Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:
(a) two different ketones
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