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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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 55c
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
Verified step by step guidance1
Step 1: Begin by identifying the target compound, CD3CH2CH2OH, which is ethanol with a deuterium-labeled methyl group (CD3). The goal is to incorporate deuterium into the methyl group while maintaining the ethyl and hydroxyl groups.
Step 2: Use CD3MgBr (deuterium-labeled methyl magnesium bromide) as the Grignard reagent. This reagent will provide the CD3 group during the reaction. Select a suitable non-deuterated starting material, such as ethylene oxide (C2H4O), which can react with the Grignard reagent to form the desired alcohol.
Step 3: React ethylene oxide (C2H4O) with CD3MgBr in an anhydrous ether solvent. The Grignard reagent will attack the electrophilic carbon in the ethylene oxide, opening the epoxide ring and forming CD3CH2CH2OMgBr as an intermediate.
Step 4: Quench the reaction by adding D2O (deuterium oxide). This step will protonate the alkoxide intermediate (CD3CH2CH2OMgBr), replacing the magnesium bromide with a hydroxyl group and yielding the final product, CD3CH2CH2OH.
Step 5: Purify the product using standard organic chemistry techniques, such as distillation or extraction, to isolate the deuterium-labeled ethanol (CD3CH2CH2OH). Confirm the structure using spectroscopic methods like NMR to verify the incorporation of deuterium.
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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. Deuterium can be introduced into molecules using deuterated reagents, such as CD3MgBr, which provides a source of deuterium for the synthesis of labeled compounds.
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03:06
Understanding the hydrogen isotopes.
Grignard Reagents
Grignard reagents are organomagnesium compounds that are highly reactive and used to form carbon-carbon bonds in organic synthesis. In this context, CD3MgBr acts as a deuterated Grignard reagent, allowing for the introduction of a deuterated methyl group into a target molecule. Understanding the reactivity and mechanisms of Grignard reagents is essential for successfully synthesizing complex organic compounds.
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02:12Carbonation of Grignard Reagents
Alcohol Synthesis
The synthesis of alcohols from alkenes or other functional groups is a fundamental reaction in organic chemistry. In this case, the target compound CD3CH2CH2OH can be synthesized through nucleophilic addition of the deuterated Grignard reagent to a suitable carbonyl compound, followed by hydrolysis with D2O. Recognizing the steps involved in alcohol formation is key to constructing the desired deuterium-labeled compound.
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02:26Forming alcohols through Oxymercuration-Reduction.
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.
a. CH3CH(OD)CD3
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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
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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
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
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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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