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 55d
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
Verified step by step guidance1
Start with a non-deuterated benzaldehyde (PhCHO) as your starting material. This compound contains a benzene ring attached to a carbonyl group, which will serve as the electrophilic site for the Grignard reaction.
Prepare the Grignard reagent CD3MgBr. This reagent is a source of the deuterium-labeled methyl group (CD3) and will act as the nucleophile in the reaction.
React PhCHO with two equivalents of CD3MgBr. The first equivalent will add a CD3 group to the carbonyl carbon, forming an intermediate alkoxide. The second equivalent will add another CD3 group, resulting in the formation of Ph(CD3)2C−OMgBr.
Perform an acidic workup using D2O. The D2O will protonate the alkoxide group, replacing the oxygen-bound hydrogen with deuterium, yielding the final product Ph(CD3)2COD.
Isolate and purify the product Ph(CD3)2COD using standard organic chemistry techniques such as extraction, drying, and distillation or recrystallization.
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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 reaction pathways and studying mechanisms in organic chemistry. In this question, CD3MgBr serves as a source of deuterium, allowing for the incorporation of deuterium into the final product.
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Understanding the hydrogen isotopes.
Grignard Reagents
Grignard reagents, such as CD3MgBr, are organomagnesium compounds that react with various electrophiles to form carbon-carbon bonds. They are highly reactive and can be used to introduce deuterium into organic molecules. Understanding their reactivity and how they interact with other functional groups is essential for synthesizing the desired deuterium-labeled compound.
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Deuterated Alcohols
Deuterated alcohols, like Ph(CD3)2COD, are compounds where deuterium replaces hydrogen in the hydroxyl group or alkyl chains. The synthesis of such compounds often involves reactions with deuterated reagents and can be used in various applications, including NMR spectroscopy. Recognizing how to form these compounds through specific reactions is key to solving the question.
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Related Practice
Textbook Question
Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:
(b) two different alkenes
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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:
(c) an ester
692
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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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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
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
1368
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