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
views
Ch.10 - Structure and Synthesis of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 55a
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
Verified step by step guidance1
Step 1: Begin with a non-deuterated starting material, such as acetone (CH3COCH3). Acetone is a good choice because it contains a ketone functional group that can undergo nucleophilic addition reactions.
Step 2: React acetone with CD3MgBr (deuterium-labeled methylmagnesium bromide). This is a Grignard reagent, which will attack the carbonyl carbon of acetone, forming a tertiary alcohol intermediate. The reaction mechanism involves nucleophilic addition of the CD3 group to the carbonyl carbon.
Step 3: After the Grignard reaction, the intermediate will have a tertiary alcohol group. To introduce the deuterium-labeled hydroxyl group (-OD), perform a proton exchange reaction by treating the intermediate with D2O (deuterium oxide). This will replace the hydrogen in the hydroxyl group with deuterium.
Step 4: Verify the structure of the final product, CH3CH(OD)CD3. The molecule should now have one deuterium atom in the hydroxyl group (-OD) and three deuterium atoms in the methyl group (-CD3).
Step 5: Ensure proper purification of the product using techniques such as distillation or chromatography to isolate CH3CH(OD)CD3 from any side products or unreacted starting materials.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
5mWas this helpful?
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 the context of the question, deuterium from CD3MgBr and D2O will be incorporated into the target compound to create specific isotopomers.
Recommended video:
Guided course
03:06
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 how Grignard reagents function is essential for synthesizing the desired deuterium-labeled compound in the question.
Recommended video:
Guided course
02:12Carbonation of Grignard Reagents
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, the deuterated Grignard reagent acts as a nucleophile, attacking a suitable electrophile to form the desired product. Recognizing the conditions and mechanisms of nucleophilic substitution is vital for successfully synthesizing the target compound.
Recommended video:
Guided course
01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
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
843
views
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
views
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
1304
views
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
views
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
1387
views