Treatment of 1,2-dimethylcyclopentene with OsO4, followed by aqueous NaHSO3, produces which of the following: Oll O III OIV OV OI OH CH3 CH3 OH II OH CH3 OH CH3 III OH CH3 H CH3 CH3 H for IV "OH CH3 CH3 H "H CH3
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- Which of the following is/are the expected product/s of the reaction of 2-pentanone (CH3COCH2CH2CH3) with excess Br2, followed by OH-? CHBr3 + CH3CH2CH2COOH BrCH2COCH2CH2CH3 CHBr3 + CH3CH2CH2COO- CH3COCHBrCH2CH3An 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.)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 reaction of 2-ethyl-1-pentene with Br2, with H2 + Pd/C, or with R2BH/THF followed by aqueous HO- + H2O2 leads to a racemic mixture. Explain why a racemic mixture is obtained in each case.Although diazomethane (CH2N2) is often not a useful reagent forpreparing cyclopropanes, other diazo compounds give good yields ofmore complex cyclopropanes. Draw a stepwise mechanism for theconversion of diazo compound A to B, an intermediate in the synthesisof sirenin, the sperm attractant produced by the female gametes of thewater mold Allomyces.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.
- Propose a detailed mechanism for the transformations presented. represent the Intermediate structure A.Devise a synthesis of (E)-1-phenylhex-1-ene (CH3CH2CH2CH2CH = CHPh) using hydrocarbons having ≤ 6 C’s and a Suzuki reaction as one of the steps.How can X be prepared from a constitutional isomer by a series of [2 + 2]cycloaddition reactions? Interest in molecules that contain severalcyclobutane rings fused together has been fueled by the discovery ofpentacycloanammoxic acid methyl ester, a lipid isolated from themembrane of organelles in the bacterium Candidatus Brocadiaanammoxidans. The role of this unusual natural product is as yetunknown.
- Suggest a detailed mechanism for the reaction below. Represent the product in the most stable conformation and also its stereochemistry (Identify stereogenic centers as R or S)What products would ypu obtain from reaction of 2,4-dimethyl-2-pentene with BH3, followed by H2O2, OH-? Show its complete reaction mechanism.When N-bromosuccinimide is added to hex-1-ene in CCl4 and a sunlamp is shone on themixture, three products result.(a) Give the structures of these three products