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1,2,2-trimethylcyclopentan-1-ol is heated in aqueous sulfuric acid f. (3S, 4S)-4-methyl-3-hexanol is heated in aqueous sulfuric acid

1,2,2-trimethylcyclopentan-1-ol is heated in aqueous sulfuric acid f. (3S, 4S)-4-methyl-3-hexanol is heated in aqueous sulfuric acid

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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**Transcription for Educational Use:** **e.** Name the major product(s) of this reaction only. 1,2,2-trimethylcyclopentan-1-ol is heated in aqueous sulfuric acid. **f.** (3S, 4S)-4-methyl-3-hexanol is heated in aqueous sulfuric acid. **Explanation of Reactions:** - For part **e**, the reaction involves 1,2,2-trimethylcyclopentan-1-ol in the presence of aqueous sulfuric acid, which typically leads to dehydration reactions that form alkenes. Sulfuric acid acts as a catalyst promoting the loss of a water molecule from the alcohol to produce an alkene – in this case, the major product is likely to be a more stable alkene configuration. - For part **f**, (3S, 4S)-4-methyl-3-hexanol undergoes a similar dehydration process when heated with aqueous sulfuric acid. The stereochemistry indicated by (3S, 4S) suggests a specific 3D arrangement of the molecules, which can influence the type of alkene formed as the major product, often favoring formations that lead to greater stability and possible rearrangements. These reactions are representative of typical elimination reactions in organic chemistry, which are crucial in understanding the formation of alkenes from alcohols.
Transcribed Image Text:**Transcription for Educational Use:** **e.** Name the major product(s) of this reaction only. 1,2,2-trimethylcyclopentan-1-ol is heated in aqueous sulfuric acid. **f.** (3S, 4S)-4-methyl-3-hexanol is heated in aqueous sulfuric acid. **Explanation of Reactions:** - For part **e**, the reaction involves 1,2,2-trimethylcyclopentan-1-ol in the presence of aqueous sulfuric acid, which typically leads to dehydration reactions that form alkenes. Sulfuric acid acts as a catalyst promoting the loss of a water molecule from the alcohol to produce an alkene – in this case, the major product is likely to be a more stable alkene configuration. - For part **f**, (3S, 4S)-4-methyl-3-hexanol undergoes a similar dehydration process when heated with aqueous sulfuric acid. The stereochemistry indicated by (3S, 4S) suggests a specific 3D arrangement of the molecules, which can influence the type of alkene formed as the major product, often favoring formations that lead to greater stability and possible rearrangements. These reactions are representative of typical elimination reactions in organic chemistry, which are crucial in understanding the formation of alkenes from alcohols.
1. For the following elimination reactions (i) Write bond-line structure of the substrate and the reagent (ii) Write full mechanism for the reaction (transition state for E2, intermediate for E1) and name the reaction either as E1 or E2; (iii) Write all possible products of the reaction defining which one/s is/are major and which one/s is/are minor; (iv) Name products of the reaction if requested.
Transcribed Image Text:1. For the following elimination reactions (i) Write bond-line structure of the substrate and the reagent (ii) Write full mechanism for the reaction (transition state for E2, intermediate for E1) and name the reaction either as E1 or E2; (iii) Write all possible products of the reaction defining which one/s is/are major and which one/s is/are minor; (iv) Name products of the reaction if requested.
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