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(A) The literature reports that when alcohol 1 (see structure below) is treated with thionyl chloride in diethyl ether, the single product is (35,5S)-3- chloro-5-methylcyclohexene (2) (no enantiomer of diastereomer of 2 is formed). Explain by writing a detailed mechanism. Look at the solution to LC-39 (B) Using a mechanism, predict what single stereoisomer of 2 should form when pyridine is substituted for the diethyl ether. (C) Finally, predict mechanistically what additional stereoisomers of 3- chloro-5-methylcyclohexene should form when 1 is treated with Lucas reagent (ZnCl₂/H₂0 CI).

(A) The literature reports that when alcohol 1 (see structure below) is treated with thionyl chloride in diethyl ether, the single product is (35,5S)-3- chloro-5-methylcyclohexene (2) (no enantiomer of diastereomer of 2 is formed). Explain by writing a detailed mechanism. Look at the solution to LC-39 (B) Using a mechanism, predict what single stereoisomer of 2 should form when pyridine is substituted for the diethyl ether. (C) Finally, predict mechanistically what additional stereoisomers of 3- chloro-5-methylcyclohexene should form when 1 is treated with Lucas reagent (ZnCl₂/H₂0 CI).

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Chemistry
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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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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1. (A) (B) (C) The literature reports that when alcohol 1 (see structure below) is treated with thionyl chloride in diethyl ether, the single product is (35,5S)-3- chloro-5-methylcyclohexene (2) (no enantiomer of diastereomer of 2 is formed). Explain by writing a detailed mechanism. Look at the solution to LC-39 Using a mechanism, predict what single stereoisomer of 2 should form when pyridine is substituted for the diethyl ether. Finally, predict mechanistically what additional stereoisomers of 3- chloro-5-methylcyclohexene should form when 1 is treated with Lucas reagent (ZnCl₂/H₂O*CI). CH3 OH H CH3 H 2
Transcribed Image Text:1. (A) (B) (C) The literature reports that when alcohol 1 (see structure below) is treated with thionyl chloride in diethyl ether, the single product is (35,5S)-3- chloro-5-methylcyclohexene (2) (no enantiomer of diastereomer of 2 is formed). Explain by writing a detailed mechanism. Look at the solution to LC-39 Using a mechanism, predict what single stereoisomer of 2 should form when pyridine is substituted for the diethyl ether. Finally, predict mechanistically what additional stereoisomers of 3- chloro-5-methylcyclohexene should form when 1 is treated with Lucas reagent (ZnCl₂/H₂O*CI). CH3 OH H CH3 H 2
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