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. (d)

All right. Hi, everyone. So this question is asking us to predict the product likely to form when the following compound reacts with sodium boro hydride. That's nabh four in methanol. And our starting material is 34 dimethyl cyclin 10. Now, notably, our starting material is a ketone and this ketone is reacting with sodium boro hydride, which is a relatively mild reducing agent because sodium boro hydride is relatively mild. It's most effective with aldehydes and ketones. It's not effective with other carbon compounds such as carboxylic acid esters, et cetera. However, when it comes to an aldehyde or a ketone, sodium boro hydride is going to reduce these two functional groups into alcohols. Now, if the starting material is a ketone, the product is a secondary alcohol and primary alcohols are produced from all the heights. So here I'm going to go ahead and add a reaction arrow with sodium boro hydride on top, since that's our primary reagent and methanol on the bottom since that's going to be our solvent here. So when drawing the final product, the carbon chain is going to remain the same. So we have the same five carbon ring with two methyl groups on adjacent carpets. However, the car Bunel is going to be replaced by an oh group. There is now a single bond between carbon and oxygen because that carbon from the starting car bottle has a new hydrogen or a new bond to a hydrogen and there you have it. So that means that our final product is 34 dimethyl cyclops one. And with that being said, thank you so very much for watching. And I hope you found this helpful.

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13. Alcohols and Carbonyl Compounds

Reducing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Reducing Agent

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Problem 24d

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.
(d)

Verified step by step guidance

Step 1: Identify the functional group in the given compound. The structure provided is a cyclic ketone, specifically cyclohexanone, which contains a carbonyl group (C=O).

Step 2: Understand the role of NaBH4 in organic reactions. Sodium borohydride (NaBH4) is a reducing agent commonly used to reduce ketones and aldehydes to their corresponding alcohols.

Step 3: Predict the reaction mechanism. NaBH4 donates hydride ions (H⁻) to the electrophilic carbon of the carbonyl group, breaking the double bond and forming a single bond with the addition of a hydrogen atom.

Step 4: Consider the solvent methanol. Methanol acts as a proton source, providing a hydrogen atom to the oxygen atom of the carbonyl group, completing the reduction process.

Step 5: Determine the product. The reduction of cyclohexanone with NaBH4 in methanol will yield cyclohexanol, a secondary alcohol, as the product.

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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 Reactions

The mechanism of reduction reactions typically involves the nucleophilic attack of the hydride ion on the carbonyl carbon, followed by protonation to form an alcohol. This process can be visualized in two steps: first, the formation of a tetrahedral intermediate, and then the collapse of this intermediate to yield the alcohol product. Familiarity with this mechanism helps in 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, which can stabilize charged intermediates and facilitate proton transfer. Understanding how solvents affect reaction rates, product distribution, and the stability of intermediates is essential for accurately predicting the products of the reaction with NaBH4.

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