Compounds containing deuterium (D = 2 H) are useful for kinetic studies and metabolic studies with new pharmaceuticals. One way to introduce deuterium is by using the reagent LiAlD 4 , equivalent in reactivity to LiAlH 4 . Show how to make these deuterium-labeled compounds, using LiAlD 4 and D 2 O as your sources of deuterium, and any non-deuterated starting materials you wish. (c) CH 3 CD 2 OD

All right. Hello everyone. So this question is asking us to illustrate how to obtain the following deuterium labeled compound using Liald four and D 20 as the sources of deuterium and any non deuter starting materials. Here, the intended product is CH three CH two CD two OD. So let's go ahead and start by drawing the intended products. Here, we have a three carbon chain and on carbon number one of the chain, we have a deterd hydroxy group. So that's OD and two additional atoms of deuterium attached directly to carbon. Number one. Now recall that deuterium is an isotope of hydrogen with a massive tooth. Now, let's go ahead and start by talking about the role of Liald four in this synthesis. Now, Liald four looks very similar to lithium aluminum hydroxide. That's Lialh four. Lithium aluminum hydride is an example of a strong reducing agent that converts Carboni groups into alcohols. And the way that it does so is by having a hydride ion that is hydrogen with a low pair of electrons directly attack the carbo carbon, which creates a oxide ion. Now, we can see here that in the structure of the intended product. There are actually two deuterium atoms attached to carbon number one. And so what that implies is that that addition happened twice. This is because Liald four is going to behave in a similar way as lithium aluminum hydride, which is why it's important to bring that up first. So here recall that compounds like carboxylic acids react with lithium aluminum hydrated twice to ultimately produce a primary alcohol. This means that our starting material is going to ultimately be a three carbon carboxylic acid. But there is one more step because earlier, I mentioned that after lithium aluminum hydroxide and in this case, lald four adds on to the carbon carbon. After both additions, ultimately, an oxide ion is produced. And so a separate step is needed to proton the oxide ion and give us a neutral product. In this particular case, instead of having hydrogen attached to the oxygen of our product, there's another deuterium atom instead. So D 20 in this case, is going to behave as an acid and it's going to provide the deuterium atom that is attached to oxygen in the final product. And so the synthesis is ultimately as follows. Our starting material is a three carbon carboxylic acid. So that's propo OIC acid. And in the first step, we introduce our reducing agent Liald four, which similar to lithium aluminum hydride is going to add deuterium twice to the carbon carbon. And then in the second step, D 20 is going to be used during the usual protonation step of the oxide ion resulting in another deuterium atom attached to oxygen and there you have it. So with that being said, thank you so very much for watching and I hope you found this helpful.

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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
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8. Elimination Reactions2h 30m
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10. Addition Reactions3h 19m
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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
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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
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26. Amines1h 43m
27. Heterocycles2h 0m
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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

Reducing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Reducing Agent

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Problem 54c

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

Verified step by step guidance

Step 1: Understand the problem. The goal is to synthesize CH3CD2OD, a deuterium-labeled compound, using LiAlD4 and D2O as sources of deuterium. LiAlD4 is a reducing agent that introduces deuterium (D) in place of hydrogen (H). D2O is heavy water, which can also provide deuterium atoms.

Step 2: Select a suitable non-deuterated starting material. For this synthesis, CH3CHO (acetaldehyde) is a good choice because it contains a carbonyl group that can be reduced by LiAlD4.

Step 3: Perform the reduction of CH3CHO using LiAlD4. The hydride-like deuterium from LiAlD4 will reduce the carbonyl group to form CH3CD2OH. This step involves nucleophilic attack of the deuterium on the carbonyl carbon, followed by protonation.

Step 4: Exchange the hydroxyl hydrogen in CH3CD2OH with deuterium using D2O. This can be achieved by treating CH3CD2OH with D2O under acidic or basic conditions, allowing the hydroxyl hydrogen to be replaced by deuterium, forming CH3CD2OD.

Step 5: Verify the structure of the final product, CH3CD2OD, ensuring that the deuterium atoms are correctly incorporated at the desired positions. This can be confirmed using spectroscopic techniques such as NMR or IR.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Deuterium and Its Applications

Deuterium is a stable isotope of hydrogen, represented as D or 2H, containing one proton and one neutron. Its unique properties make it valuable in kinetic and metabolic studies, particularly in pharmaceuticals, as it can help trace reaction pathways and metabolic processes without altering the chemical behavior of the compounds.

Lithium Aluminum Deuteride (LiAlD4)

LiAlD4 is a powerful reducing agent similar to LiAlH4 but contains deuterium instead of hydrogen. It is used to introduce deuterium into organic compounds through reduction reactions, allowing for the synthesis of deuterated compounds, which are essential for studying reaction mechanisms and dynamics in organic chemistry.

Deuterated Alcohol Synthesis

The synthesis of deuterated alcohols, such as CH3CD2OD, involves the reaction of non-deuterated starting materials with deuterium sources like LiAlD4 and D2O. This process typically includes reduction steps where the deuterium replaces hydrogen atoms, resulting in the formation of deuterated products that can be used in various analytical and experimental applications.

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