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the following reactions are discussed. Ts is the tolunesulfonyl group. CH; Tolunesulfonyl group (Ts) (a) OH OTs pyridine + C-Ts + HCI (S)-2-Octanol (S)-2-Octyl tosylate (b) OTS Sy2 ONa+ + + Na OTs ethanol Sodium acetate (S)-2-Octyl tosylate (R)-2-Octyl acetate In reaction (a), an S compound gives an S product. In reaction (b), an S compound gives an R product. Explain what is probably going on. (Hint: The oxygen atom in the starting material and product is the same in one reaction but not in the other.) What might this say about the second reaction?

the following reactions are discussed. Ts is the tolunesulfonyl group. CH; Tolunesulfonyl group (Ts) (a) OH OTs pyridine + C-Ts + HCI (S)-2-Octanol (S)-2-Octyl tosylate (b) OTS Sy2 ONa+ + + Na OTs ethanol Sodium acetate (S)-2-Octyl tosylate (R)-2-Octyl acetate In reaction (a), an S compound gives an S product. In reaction (b), an S compound gives an R product. Explain what is probably going on. (Hint: The oxygen atom in the starting material and product is the same in one reaction but not in the other.) What might this say about the second reaction?

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 28VC
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the following reactions are discussed. Ts is the tolunesulfonyl group. CH; Tolunesulfonyl group (Ts) (a) OH OTs pyridine + C-Ts + HCI (S)-2-Octanol (S)-2-Octyl tosylate (b) OTS Sy2 ONa+ + + Na OTs ethanol Sodium acetate (S)-2-Octyl tosylate (R)-2-Octyl acetate In reaction (a), an S compound gives an S product. In reaction (b), an S compound gives an R product. Explain what is probably going on. (Hint: The oxygen atom in the starting material and product is the same in one reaction but not in the other.) What might this say about the second reaction?
Transcribed Image Text:the following reactions are discussed. Ts is the tolunesulfonyl group. CH; Tolunesulfonyl group (Ts) (a) OH OTs pyridine + C-Ts + HCI (S)-2-Octanol (S)-2-Octyl tosylate (b) OTS Sy2 ONa+ + + Na OTs ethanol Sodium acetate (S)-2-Octyl tosylate (R)-2-Octyl acetate In reaction (a), an S compound gives an S product. In reaction (b), an S compound gives an R product. Explain what is probably going on. (Hint: The oxygen atom in the starting material and product is the same in one reaction but not in the other.) What might this say about the second reaction?
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