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c) Show the product formed at each of the three steps that connects starting material to the end target. Attack it from both ends. Deuterium (D) is just an isotope of hydrogen (H). HO H (primary alcohol) TosCl pyridine D HC C: H CH₂CH=NOH H₂NOH (H₂SO4) -H₂O HB 2 2. H₂O2, NaOH

c) Show the product formed at each of the three steps that connects starting material to the end target. Attack it from both ends. Deuterium (D) is just an isotope of hydrogen (H). HO H (primary alcohol) TosCl pyridine D HC C: H CH₂CH=NOH H₂NOH (H₂SO4) -H₂O HB 2 2. H₂O2, NaOH

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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Predict the product.
To understand the synthesis pathway, refer to the following steps and reactions: 1. **Primary Alcohol Transformation:** - The starting material is a primary alcohol with the structure depicted as HO-CH₂-CHD. - This compound undergoes a reaction with tosyl chloride (TsCl) in the presence of pyridine, resulting in the formation of a tosylate intermediate. This step replaces the hydroxyl group (OH) with a tosyl (OTs) group. 2. **Alkyne Formation:** - The resulting tosylate then undergoes a nucleophilic substitution with an acetylide ion (HC≡C⁻), forming an alkyne via an SN2 mechanism. The deuterium (D) is retained in the structure. 3. **Final Product Formation:** - The alkyne is subsequently transformed via hydroboration-oxidation reactions: 1. The alkyne reacts with a borane (BH₃ or a similar reagent), followed by hydrogen peroxide (H₂O₂) and sodium hydroxide (NaOH) to afford an anti-Markovnikov addition product, an alcohol. 2. The reaction sequence yields a structure where the position of the hydroxyl group is determined by the regioselectivity of the reagents. Overall, the sequence illustrates the transformation of a primary alcohol into a specified final product through sequential substitution, elimination, and addition reactions, explicitly noting the retention and position of deuterium atoms throughout the process.
Transcribed Image Text:To understand the synthesis pathway, refer to the following steps and reactions: 1. **Primary Alcohol Transformation:** - The starting material is a primary alcohol with the structure depicted as HO-CH₂-CHD. - This compound undergoes a reaction with tosyl chloride (TsCl) in the presence of pyridine, resulting in the formation of a tosylate intermediate. This step replaces the hydroxyl group (OH) with a tosyl (OTs) group. 2. **Alkyne Formation:** - The resulting tosylate then undergoes a nucleophilic substitution with an acetylide ion (HC≡C⁻), forming an alkyne via an SN2 mechanism. The deuterium (D) is retained in the structure. 3. **Final Product Formation:** - The alkyne is subsequently transformed via hydroboration-oxidation reactions: 1. The alkyne reacts with a borane (BH₃ or a similar reagent), followed by hydrogen peroxide (H₂O₂) and sodium hydroxide (NaOH) to afford an anti-Markovnikov addition product, an alcohol. 2. The reaction sequence yields a structure where the position of the hydroxyl group is determined by the regioselectivity of the reagents. Overall, the sequence illustrates the transformation of a primary alcohol into a specified final product through sequential substitution, elimination, and addition reactions, explicitly noting the retention and position of deuterium atoms throughout the process.
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