Show how to make these deuterium-labeled compounds, using CD 3 MgBr and D 2 O as your sources of deuterium, and any non-deuterated starting materials you wish. c. CD 3 CH 2 CH 2 OH

Welcome back, everyone show how to make the deuterium labeled compound below using CD three M GBR and H2O. Now specifically, if we carefully think about the reaction of interest were given the guard region because it's CD three bonded to M GBR. So this form is the Grainer rent and we have to recall that the Granite Regent is basic. If we carefully look at the product formed, it is a tertiary alcohol, right? And we want to perform a granard reaction. One of the ways to perform this reaction is to use an oxide. So essentially, if the granite agent is basic, it is going to attack the less substituted carbon of the epoxy, specifically, the peroxide is going to be formed with oxygen from the alcohol group, right? So to draw the starting material, we simply want to get that three membered ring. Let's draw it out between carbons, one and two. What else do we have? Well, we have two metal groups bonded to carbon number two. Now CD three comes from the grain regent because it is basic, it is going to attack the less substituted end of the oxide. So let's see how it works. The first step of the reaction is the addition of the greener grat CD three M GB R. We are going to observe the nucleic attack step followed by ring opening and the formation of the al coite anion. And the second step is the acidic work up. In this case, it's sufficient to use water. And that's our second step of the reaction. We have the protonation step. The alcide anion simply gets proton it into an alcohol. Well, then we have our synthesis scheme. Let's label it as our final answer. Thank you for watching.

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1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

13. Alcohols and Carbonyl Compounds

Grignard Reaction

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Grignard Reaction

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3:04 minutes

Problem 55c

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

Verified step by step guidance

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.

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.

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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Textbook Question

Two of the methods for converting alkyl halides to carboxylic acids are covered in Sections 20-8B and 20-8C. One is formation of a Grignard reagent followed by addition of carbon dioxide and then dilute acid. The other is substitution by cyanide ion, followed by hydrolysis of the resulting nitrile. For each of the following conversions, decide whether either or both of these methods would work, and explain why. Show the reactions you would use.

(e)

(f)

Textbook Question

Grignard reagents react slowly with oxetane to produce primary alcohols. Propose a mechanism for this reaction, and suggest why oxetane reacts with Grignard reagents even though most ethers do not.

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(f)

(g)

Textbook Question

Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.

(g) cyclopentylphenylmethanol from benzaldehyde (Ph–CHO)

Textbook Question

Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:

Textbook Question

Show how you would synthesize the following primary alcohol by adding an appropriate Grignard reagent to formaldehyde.

(c)

Textbook Question

Show two ways you could synthesize each of the following secondary alcohol by adding an appropriate Grignard reagent to an aldehyde.

(c)

Textbook Question

Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

c. 1-ethylcyclopentanol

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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

Key Concepts

Deuterium Labeling

Grignard Reagents

Alcohol Synthesis

Watch next

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