Complete the mechanism for the DIBAL-H (diisobutylaluminum hydride) reduction of methyl cyclopentanecarboxylate at -78 °C in hexane solvent by adding any missing atoms, bonds, charges, nonbonding electron pairs, and curved arrows. Step 1: Draw a curved arrow. Step 2: Complete the intermediate, then draw curved arrows. Select Draw Rings More Erase Select Draw. Rings More Erase C H H the O Al H : 04 Cognition (4) docx W Cognition (3).docx

Complete the mechanism for the DIBAL-H (diisobutylaluminum hydride) reduction of methyl cyclopentanecarboxylate at -78 °C in hexane solvent by adding any missing atoms, bonds, charges, nonbonding electron pairs, and curved arrows. Step 1: Draw a curved arrow. Step 2: Complete the intermediate, then draw curved arrows. Select Draw Rings More Erase Select Draw. Rings More Erase C H H the O Al H : 04 Cognition (4) docx W Cognition (3).docx

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

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.24P: Pyridine exhibits a UV transition of the type n at 270 nm. In this transition, one of the unshared...

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Interestingly, reduction of the complex shown above mostly gives thealcohol enantiomer shown below after workup. a. Draw the other minor diastereomeric alcohol product. b. Briefly explain the diastereoselectivity of the reduction – why is oneenantiomer heavily favored? Draw a structure or structures to support youranswer.
An inexperienced graduate student treated dec-5-ene with borane in THF, placed the flask in a refrigerator, and left for aparty. When he returned from the party, he discovered that the refrigerator was broken and that it had gotten quite warminside. Although all the THF had evaporated from the flask, he treated the residue with basic hydrogen peroxide. Tohis surprise, he recovered a fair yield of decan-1-ol. Use a mechanism to show how this reaction might have occurred.(Hint: The addition of BH3 is reversible.)
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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(CzHs)3). 3SnCl4 + 4Al(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 0.257L of tetraethylstannane (d= 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?
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 + 4Al(C2H5)3 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.230 L of SnCl4 (d = 2.226 g/mL) was treated with 0.396 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). If 0.335 L of tetraethylstannane (d = 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?
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