Predict the products you would expect from the reaction of NaBH 4 with the following compounds. You may assume that these reactions take place in methanol as the solvent. (f)

All right. Hello everyone. So this question is asking us to predict the product likely to form when the given compound reacts with sodium boro hydride. That's nabh four in methanol. So when considering the structure of the starting material more closely the primary functional group, her groups is that of an ester and an aldehyde. And the other reagent in question is sodium boro hydride in the presence of methano as a solvent. Now recall that sodium boro hydride is a relatively mild reducing agent. And it's important to recognize that sodium boro hydride is relatively mild because it limits what functional groups are going to be affected by the use of sodium boro hydrx. Specifically sodium boro hydride is effective in the reduction of aldehydes and ketones to produce primary and secondary alcohols respectively. However, sodium boro hydride is not strong enough to react with other Carboni compounds such as carboxylic acids, esters and others. And so in this particular case, the er is not going to react with sodium boro hydride, which means that it's going to remain intact in the structure of the final product. On the other hand, the aldehyde is going to be reduced into a primary alcohol. And so when drawing out the structure of the final product, the car bottle of the aldehyde is replaced with a hydroxy group. So with that in mind, we can go ahead and draw the final product first, we have the Esther that's not going to change. And then towards the right side, we have a hydroxy group to create a primary alcohol from the given all the height and there you have it. And 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
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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2:51 minutes

Problem 24f

Textbook Question

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(f)

Verified step by step guidance

Step 1: Identify the functional groups in the given compound. The structure contains an aldehyde group (-CHO) and a lactone (cyclic ester). These are the groups that can potentially react with NaBH4.

Step 2: Understand the reactivity of NaBH4. Sodium borohydride (NaBH4) is a reducing agent that selectively reduces aldehydes and ketones to their corresponding alcohols. It does not typically reduce esters under mild conditions.

Step 3: Predict the reduction of the aldehyde group. The aldehyde group (-CHO) will be reduced to a primary alcohol (-CH2OH) by NaBH4 in methanol solvent.

Step 4: Consider the lactone group. Since NaBH4 does not reduce esters under these conditions, the lactone group will remain unchanged in the product.

Step 5: Combine the results. The final product will have the aldehyde group converted to a primary alcohol, while the lactone group remains intact. The structure of the product will reflect these changes.

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Key Concepts

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

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state by a molecule. In organic chemistry, this often refers to the conversion of carbonyl compounds (like aldehydes and ketones) into alcohols. Sodium borohydride (NaBH4) is a common reducing agent that selectively reduces these functional groups, making it essential to understand its reactivity in predicting products.

Sodium Borohydride (NaBH4)

Sodium borohydride is a mild reducing agent used primarily for the reduction of aldehydes and ketones to their corresponding alcohols. It is less reactive than lithium aluminum hydride, allowing for selective reductions without affecting other functional groups. Understanding its mechanism and selectivity is crucial for predicting the outcome of reactions involving carbonyl compounds.

Solvent Effects in Organic Reactions

The choice of solvent can significantly influence the course of organic reactions. In this case, methanol serves as a polar protic solvent that can stabilize ions and facilitate the reaction between NaBH4 and the carbonyl compound. Recognizing how solvents affect reaction rates, product distributions, and mechanisms is vital for accurate predictions in organic chemistry.

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Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent.(f)

Key Concepts

Reduction Reactions

Sodium Borohydride (NaBH4)

Solvent Effects in Organic Reactions

Watch next

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(f)