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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?When 3-methyl-1-butene is reacted with 9-borabicyclo[3.3.1]nonane, the "1-ol" product is formed. What is the detailed reactin scheme for the transformation? Describe the purification procedure.
- 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.)Cembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV absorption at 245 nm, but dihydrocembrene (C20H34), the product of hydrogenation with 1 equivalent of H2, has no UV absorption. On exhaustive hydrogenation, 4 equivalents of H2 react, and octahydrocembrene, C20H40, is produced. On ozonolysis of cembrene, followed by treatment of the ozonide with zinc, four carbonylcontaining products are obtained: Propose a structure for cembrene that is consistent with its formation from geranylgeranyl diphosphate.Ozonolysis of compound D will produce compound E and compound F as products. Hydrationof compound D will produce compound G as major product. Compound D is a major productobtained from dehydrohalogenation of 2-chloro-3-methylbutane. a) Identify the structural formula for compound D, E, F and G.b) Suggest suitable reagent(s) and condition(s) needed for dehydrohalogenation of 2-chloro-3-methylbutane
- Stereoisomers of α-bromocinnamic acid: draw the reaction mechiansim with arows for the dehydrobromination of 2,3-dibromo-3-phenylpropanoic acid with ethanol and KOH to produce (Z)-α-bromocinnamic acid and (E)-α-bromocinnamic acid. Also draw the transition state for The (Z)-isomer syn-periplanar transition state and anti-periplanar transition state of the (E)-isomer.showed the synthesis of dec-3-yne by adding the hexyl groupfirst, then the ethyl group. Show the reagents and intermediates involved in theother order of synthesis of dec-3-yne, by adding the ethyl group first and the hexylgroup last.w how enols, enolate ions, andenamines act as nucleophiles. Predictthe products of their reactions withhalogens, alkyl halides, and otherelectrophiles. Show how they areuseful in synthesis.
- The hydroboration–oxidation of internal alkynes produces ketones.(a) When hydroboration–oxidation is applied to but-2-yne, a single pure product isobtained. Determine the structure of this product, and show the intermediates in itsformation.(b) When hydroboration–oxidation is applied to pent-2-yne, two products are obtained.Show why a mixture of products should be expected with any unsymmetricalinternal alkyne.Acetoxybenzene (PhOC(=O)OCH3) is much less reactive than ethoxybenzene (PhOCH2CH3) in electrophilic aromatic substitution reactions. Suggest an explanation for this result, based on an analysis of the inductive and resonance electronic effects of the two substituents on the stability of theWheland intermediate for para substitution by an electrophile E+The hydrocrbon B undergoes catalytic hydrogenation (H2, Pd/C) to give 1-isopropyl-4-methylcyclohexane. Using the ozonolysis products for B as a guide, reconstruct the structures of B.