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What is the major organic product obtained from the following reaction? A. B. OH O ge OH OH H H 1. NaBH4 2. proton source D. O OH OH OH H OH

What is the major organic product obtained from the following reaction? A. B. OH O ge OH OH H H 1. NaBH4 2. proton source D. O OH OH OH H OH

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter16: Synthesis Workshop 1
Section: Chapter Questions
Problem 24CTQ
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**Question:** What is the major organic product obtained from the following sequence of reactions? **Reaction Scheme:** The reaction involves a starting carbonyl compound reacting with methylmagnesium bromide (\( \text{CH}_3\text{MgBr} \)) followed by acidic workup (\( \text{H}_2\text{O}^+ \)), and then an oxidation with pyridinium chlorochromate (PCC). **Options:** A. The product is a secondary alcohol with an attached methyl group. B. The product is a ketone with a methyl group on the carbon adjacent to the carbonyl carbon. C. The product is a secondary alcohol with a methyl group on the end of the chain. D. The product is a ketone similar to option B but with a different structure indicated by the placement. **Explanation:** This exercise involves determining the major product of an organic reaction sequence involving Grignard addition to an aldehyde or ketone followed by oxidation.
Transcribed Image Text:**Question:** What is the major organic product obtained from the following sequence of reactions? **Reaction Scheme:** The reaction involves a starting carbonyl compound reacting with methylmagnesium bromide (\( \text{CH}_3\text{MgBr} \)) followed by acidic workup (\( \text{H}_2\text{O}^+ \)), and then an oxidation with pyridinium chlorochromate (PCC). **Options:** A. The product is a secondary alcohol with an attached methyl group. B. The product is a ketone with a methyl group on the carbon adjacent to the carbonyl carbon. C. The product is a secondary alcohol with a methyl group on the end of the chain. D. The product is a ketone similar to option B but with a different structure indicated by the placement. **Explanation:** This exercise involves determining the major product of an organic reaction sequence involving Grignard addition to an aldehyde or ketone followed by oxidation.
**Question:** What is the major organic product obtained from the following reaction? **Reaction Scheme:** - Reactant: A cyclic compound with two carbonyl groups (C=O) positioned at the 2nd and 4th carbon atoms relative to a reference point marked with H. - Reagents: 1. NaBH₄ 2. Proton source **Options for Major Organic Product:** A. A cyclic compound with one hydroxyl group (OH) at the 2nd carbon and one carbonyl group at the 4th carbon. B. A cyclic compound with hydroxyl groups (OH) at both the 2nd and 4th carbon atoms. C. A cyclic compound with one carbonyl group at the 2nd carbon and one hydroxyl group (OH) at the 4th carbon. D. A cyclic compound with hydroxyl groups (OH) at both the 2nd and 3rd carbon atoms. **Explanation of the Reaction:** NaBH₄ (sodium borohydride) is a reducing agent typically used to reduce ketones and aldehydes to alcohols. In this reaction, the presence of NaBH₄ followed by a proton source suggests that the carbonyl groups present in the compound will likely be reduced to hydroxyl groups (alcohols). **Expected Outcome:** Since there are two carbonyl groups, they will both be converted to hydroxyl groups. Therefore, the major product will most likely be option B, where both carbonyl groups are reduced to alcohols, resulting in hydroxyl groups at the 2nd and 4th carbon positions.
Transcribed Image Text:**Question:** What is the major organic product obtained from the following reaction? **Reaction Scheme:** - Reactant: A cyclic compound with two carbonyl groups (C=O) positioned at the 2nd and 4th carbon atoms relative to a reference point marked with H. - Reagents: 1. NaBH₄ 2. Proton source **Options for Major Organic Product:** A. A cyclic compound with one hydroxyl group (OH) at the 2nd carbon and one carbonyl group at the 4th carbon. B. A cyclic compound with hydroxyl groups (OH) at both the 2nd and 4th carbon atoms. C. A cyclic compound with one carbonyl group at the 2nd carbon and one hydroxyl group (OH) at the 4th carbon. D. A cyclic compound with hydroxyl groups (OH) at both the 2nd and 3rd carbon atoms. **Explanation of the Reaction:** NaBH₄ (sodium borohydride) is a reducing agent typically used to reduce ketones and aldehydes to alcohols. In this reaction, the presence of NaBH₄ followed by a proton source suggests that the carbonyl groups present in the compound will likely be reduced to hydroxyl groups (alcohols). **Expected Outcome:** Since there are two carbonyl groups, they will both be converted to hydroxyl groups. Therefore, the major product will most likely be option B, where both carbonyl groups are reduced to alcohols, resulting in hydroxyl groups at the 2nd and 4th carbon positions.
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