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. (e)

Welcome back, everyone predict the product likely to form when the given compound reacts with sodium bar hydrate in the presence of methanol as a solvent. We're given a car bono compound. And as the problem suggests, it reacts with sodium V hydride in the presence of MA C 30 And we have to recall that sodium were hydride is a mild reducing agent. And it allows us to reduce specific car bals into alcohols. In the given structure, we're given a K zone, it is sufficiently reactive to react with sodium or hydride. We're also given an aldehyde which is even more reactive. Then a kid on meaning it will also get reduced. And we are given an answer which is the least reactive out of the three. And because ester are so unreactive, they will only be reduced by lithium aluminum hydride and not sodium bodri. So what we're going to do is reduce two out of the three corbels leaving the ester unaffected. So we're going to immediately draw the ether group. And now for the remaining carbos, we're going to turn them into corresponding alcohols. We know that keat zones get reduced to secondary alcohols So we're introducing a secondary alcohol and for the aldehyde, we have a two member chain one two, we're simply going to introduce a primary alcohol to carbon atoms, right? And an alcohol group at the end of the chain 1212 and the wage at the end, right? Because all the heights get reduced into primary alcohols. That's it. We have our final product. Thank you for watching.

Table of contents

Skip topic navigation

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

Previous problemNext problem

2:43 minutes

Problem 24e

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.
(e)

Verified step by step guidance

Step 1: Identify the functional groups in the given compound. The structure contains three carbonyl groups: one aldehyde (-CHO), one ester (-COOCH3), and one ketone (-C=O).

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

Step 4: Predict the reduction of the ketone group. The ketone group (-C=O) will be reduced to a secondary alcohol (-CH(OH)-) by NaBH4 in methanol.

Step 5: Note that the ester group (-COOCH3) will remain unchanged because NaBH4 does not reduce esters under these conditions. The final product will have a primary alcohol, a secondary alcohol, and an intact ester group.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Sodium Borohydride (NaBH4) as a Reducing Agent

Sodium borohydride (NaBH4) is a mild reducing agent commonly used in organic chemistry to reduce carbonyl compounds, such as aldehydes and ketones, to their corresponding alcohols. It donates hydride ions (H-) to the electrophilic carbon of the carbonyl group, facilitating the reduction process. Understanding its reactivity and selectivity is crucial for predicting the products of reactions involving NaBH4.

Mechanism of Reduction

The reduction mechanism typically involves the nucleophilic attack of the hydride ion on the carbonyl carbon, followed by protonation of the resulting alkoxide intermediate. This stepwise process leads to the formation of alcohols. Familiarity with this mechanism helps in visualizing how different functional groups will react with NaBH4 and what products will be formed.

Solvent Effects in Organic Reactions

The choice of solvent can significantly influence the outcome of organic reactions. In this case, methanol serves as a polar protic solvent that can stabilize charged intermediates and facilitate proton transfer. Understanding the role of the solvent is essential for predicting reaction pathways and product distributions, especially in reduction reactions where solvation can affect reactivity.

Watch next

Master Reducing Agents with a bite sized video explanation from Johnny

Start learning