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

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...

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Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.
Enamines formed from the cyclic secondary amine pyrrolidine are important intermediates in the synthesis of 1,5-diketones. (1st pic) On the structures provided below, draw arrows showing electron flow for the reaction mechanism for the acetic acid-catalyzed formation of an enamine from cyclohexanone and pyrrolidine. (2nd pic)
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One of the heptanedione isomers below has a pka of approximately 9 rather than 20. Which isomer? Why? Draw its conjugate base and offer a full explanation of its acidity.
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Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides. One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(C2H5)3). 3SnCl4 + 4AI(C2H5)3 →3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.160 L of SnCl4 (d = 2.226 g/mL) was treated with 0.346 L of triethylaluminum (Al(C2H5)3): d = 0.835 g/mL). What is the theoretical yield in this experiment (mass of tetraethylstannane, Sn(C2H5)4)? If 0.257 L of tetraethylstannane (d= 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?
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