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5. Predict all the possible products of these reactions and then identify the major product. Include stereochemistry when appropriate. Rationalize your reasoning. Assume aqueous work up to achieve neutral products. a. b. -...< MgBr NaBH4

5. Predict all the possible products of these reactions and then identify the major product. Include stereochemistry when appropriate. Rationalize your reasoning. Assume aqueous work up to achieve neutral products. a. b. -...< MgBr NaBH4

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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### Reaction Prediction with Stereochemistry and Aqueous Workup **Problem 5:** Predict all the possible products of these reactions and then identify the major product. Include stereochemistry when appropriate. Rationalize your reasoning. Assume aqueous work up to achieve neutral products. **Reaction A:** - **Reactant:** A ketone (cyclohexanone derivative) with a methyl group at the beta position. - **Reagent:** Methylmagnesium bromide (CH₃MgBr). **Reaction B:** - **Reactant:** A similar cyclohexanone derivative as in Reaction A. - **Reagent:** Sodium borohydride (NaBH₄). ### Explanation 1. **Reaction A: Grignard Reaction** - **Reactivity:** The Grignard reagent (CH₃MgBr) will act as a nucleophile and attack the electrophilic carbonyl carbon of the ketone. - **Product Formation:** The product will be a tertiary alcohol after aqueous workup, where the magnesium halide is replaced by a hydroxyl group. - **Stereochemistry:** This reaction is non-stereoselective due to the planar nature of the carbonyl group, leading to racemic mixtures in cases of chiral centers. 2. **Reaction B: NaBH₄ Reduction** - **Reactivity:** Sodium borohydride will reduce the carbonyl group of the ketone to a secondary alcohol. - **Product Formation:** The resulting product will be a cyclohexanol derivative. - **Stereochemistry:** Similarly, reduction of the ketone's planar carbonyl group may lead to racemic mixtures if relevant chiral centers are present. ### Conclusion - **Major Product Identification:** - For Reaction A, the major product is the tertiary alcohol after Grignard addition and workup. - For Reaction B, the major product is the secondary alcohol obtained from the reduction. Considerations in predicting the products involve the nature of the reagents, type of reaction, and possible stereochemical outcomes.
Transcribed Image Text:### Reaction Prediction with Stereochemistry and Aqueous Workup **Problem 5:** Predict all the possible products of these reactions and then identify the major product. Include stereochemistry when appropriate. Rationalize your reasoning. Assume aqueous work up to achieve neutral products. **Reaction A:** - **Reactant:** A ketone (cyclohexanone derivative) with a methyl group at the beta position. - **Reagent:** Methylmagnesium bromide (CH₃MgBr). **Reaction B:** - **Reactant:** A similar cyclohexanone derivative as in Reaction A. - **Reagent:** Sodium borohydride (NaBH₄). ### Explanation 1. **Reaction A: Grignard Reaction** - **Reactivity:** The Grignard reagent (CH₃MgBr) will act as a nucleophile and attack the electrophilic carbonyl carbon of the ketone. - **Product Formation:** The product will be a tertiary alcohol after aqueous workup, where the magnesium halide is replaced by a hydroxyl group. - **Stereochemistry:** This reaction is non-stereoselective due to the planar nature of the carbonyl group, leading to racemic mixtures in cases of chiral centers. 2. **Reaction B: NaBH₄ Reduction** - **Reactivity:** Sodium borohydride will reduce the carbonyl group of the ketone to a secondary alcohol. - **Product Formation:** The resulting product will be a cyclohexanol derivative. - **Stereochemistry:** Similarly, reduction of the ketone's planar carbonyl group may lead to racemic mixtures if relevant chiral centers are present. ### Conclusion - **Major Product Identification:** - For Reaction A, the major product is the tertiary alcohol after Grignard addition and workup. - For Reaction B, the major product is the secondary alcohol obtained from the reduction. Considerations in predicting the products involve the nature of the reagents, type of reaction, and possible stereochemical outcomes.
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Can you also please provide the minor products of this problems. Thanks!

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