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Predict the product for the following: H TSO to -OTS OTS 1) LiAlH4 2) H₂O 3) TSCI, pyridine ?

Predict the product for the following: H TSO to -OTS OTS 1) LiAlH4 2) H₂O 3) TSCI, pyridine ?

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 for the following reaction sequence:** 1) LiAlH₄ 2) H₂O 3) TsCl, pyridine **Given compound:** The structure shows a cyclic compound with a five-membered ring attached to an aldehyde functional group (–CHO). **Options:** 1. Cyclohexylmethyl alkene (double bond present) 2. Cyclohexylmethyl tosylate (with carbonyl group) 3. Cyclohexylmethyl alkene (double bond present) 4. Cyclohexylmethyl tosylate (with an –OTs group) 5. Cyclohexylmethyl tosylate (with an –OTs group) **Explanation:** 1) **LiAlH₄:** This is a strong reducing agent commonly used to reduce aldehydes to primary alcohols. Thus, the aldehyde group (-CHO) will be reduced to a primary alcohol (-CH₂OH). 2) **H₂O:** Water is used during the workup phase to quench the reaction and neutralize the reaction mixture. 3) **TsCl, pyridine:** Tosyl chloride (TsCl) along with pyridine (a base) is used to convert alcohols into tosylates. Tosylation converts the -OH group into an -OTs group, making it a good leaving group. **Final Product:** The aldehyde is first reduced to produce a primary alcohol, and this alcohol is then converted into a tosylate group, yielding the final product as a cyclohexylmethyl tosylate (-OTs group). Thus, the correct answer is most likely the fifth option, which shows the cyclohexylmethyl tosylate structure.
Transcribed Image Text:**Predict the product for the following reaction sequence:** 1) LiAlH₄ 2) H₂O 3) TsCl, pyridine **Given compound:** The structure shows a cyclic compound with a five-membered ring attached to an aldehyde functional group (–CHO). **Options:** 1. Cyclohexylmethyl alkene (double bond present) 2. Cyclohexylmethyl tosylate (with carbonyl group) 3. Cyclohexylmethyl alkene (double bond present) 4. Cyclohexylmethyl tosylate (with an –OTs group) 5. Cyclohexylmethyl tosylate (with an –OTs group) **Explanation:** 1) **LiAlH₄:** This is a strong reducing agent commonly used to reduce aldehydes to primary alcohols. Thus, the aldehyde group (-CHO) will be reduced to a primary alcohol (-CH₂OH). 2) **H₂O:** Water is used during the workup phase to quench the reaction and neutralize the reaction mixture. 3) **TsCl, pyridine:** Tosyl chloride (TsCl) along with pyridine (a base) is used to convert alcohols into tosylates. Tosylation converts the -OH group into an -OTs group, making it a good leaving group. **Final Product:** The aldehyde is first reduced to produce a primary alcohol, and this alcohol is then converted into a tosylate group, yielding the final product as a cyclohexylmethyl tosylate (-OTs group). Thus, the correct answer is most likely the fifth option, which shows the cyclohexylmethyl tosylate structure.
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