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. (b) CH 3 CD 2 OH

Welcome back, everyone. Deuterium containing compounds are helpful for kinetic and metabolic research with novel drugs. Lithium aluminum, deri Ragen lithium aluminum hydride counterpart in reactivity is one approach to introduce deuterium using lithium aluminum Detr and heavy water. As your sources of deuterium and other non deuter starting materials. You choose demonstrate how to create this deuterium labeled molecule CH three CH two CD 20. Now, what we notice about the given structure is that it is actually a primary alcohol. If it is a primary alcohol, we can essentially form it out of a reduction of an asset. The question is, what sort of assets should we choose? Well, essentially we have one, two and three carbons in our parent. So we're going to choose 123. So that be propo aic acid. As the problem suggests, we can use a lithium aluminum hydride. It is a strong reducing agent. And we have to recall that there are two steps. In the first step, we're using lithium aluminum high time. In the second step, we're using water. What are we producing? Well, essentially we're producing a primary alcohol and we want to use this logic to synthesize a primary alcohol that has two deuterium atoms instead of two implicit hydrogens. So lets show the actual structure that we want to form and that would be two deuterium atoms bonded to carbon one. Now, first of all, we want to recall that these two hydrogens in the first reaction are essentially bonded to the carbon carbon and the hydrogen from water is bonded to oxygen. OK. So this sells us a lot. If we want to add two deuterium atoms instead of hydrogens, we have to choose a lithium aluminum de RL I A LD four. For the first step, this gives us two deuterium atoms. And for the second step, should we choose heavy water or just water? Well, essentially that would be water because we are retaining the a age group, right? Let's label that the A age group comes from water and lithium aluminum hydride allows us to get two hydrants at the carbon. So that's the whole logic of the problem. Let's label our synthesis scheme and that's it. 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

Reducing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Reducing Agent

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Problem 54b

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

Verified step by step guidance

Step 1: Understand the problem. The goal is to synthesize CH3CD2OH, a deuterium-labeled alcohol, using LiAlD4 and D2O as sources of deuterium. LiAlD4 is a reducing agent that introduces deuterium (D) in place of hydrogen (H), and D2O can be used to exchange hydrogen atoms with deuterium.

Step 2: Select a suitable non-deuterated starting material. For this synthesis, you can start with CH3CHO (acetaldehyde), which contains a carbonyl group that can be reduced to an alcohol.

Step 3: Use LiAlD4 to reduce the carbonyl group in CH3CHO. The hydride (H-) equivalent in LiAlD4 is replaced by deuteride (D-), so the reduction will introduce deuterium atoms into the molecule. The reaction will convert CH3CHO into CH3CD2OH.

Step 4: If additional deuterium incorporation is needed, treat the product (CH3CD2OH) with D2O under acidic or basic conditions. This step allows for exchange of any remaining hydrogen atoms with deuterium from D2O.

Step 5: Verify the structure of the final product, CH3CD2OH, ensuring that the deuterium atoms are correctly incorporated at the desired positions. This can be confirmed using spectroscopic techniques such as NMR (nuclear magnetic resonance).

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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, which contains 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 specifically used for introducing deuterium into organic compounds. It reacts with various functional groups, facilitating the substitution of hydrogen atoms with deuterium, which is essential for synthesizing deuterium-labeled compounds for research purposes.

Deuterated Alcohol Synthesis

The synthesis of deuterated alcohols, such as CH3CD2OH, involves the reaction of non-deuterated starting materials with deuterium sources like LiAlD4 and D2O. This process typically includes reduction reactions where deuterium replaces hydrogen in the alcohol structure, allowing for the creation of compounds that can be used in various analytical studies.

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