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- Questão 10A certain hydrocarbon had the molecular formula C16H26 and contained two triple bonds. Ozonolysis resulted in CH3(CH2)4CO2H and HO2CCH2CH2CO2H as the only products. What is the reasonable structure for this hydrocarbon? Hexadec-6,10-dino undec-1,5-dino Hept-1,5-dino hex-1,5-dino nahWhich represents an efficient synthetic route to go from an alkane to an alkene? O elimination with NaNH2, followed by a water workup O anti-Markovnikov hydrohalogenation, followed by elimination O radical bromination, followed by elimination O hydration, followed by elimination O hydration, followed by ozonolysis of the double bondWhich of these alkyl chlorides undergoes dehydrohalogenation in the presence of a strong base to give pent-2-ene (shown below) as the only alkene product? O l-chloro-2-methylbutane O 2-chloropentane O 3-chloropentane O 1-chloropentane O l-chloro-3-methylbutane
- Select the reagent that you would use to convert an alkene to a Markovnikov (more substituted) alcohol without possibility of carbocation rearrangement. o H2SO4, H2O OBH3-THF, then H2O2, H2O, NaOH Hg(OAc)2, H2O, then NaBH4 o OsO4, TBHP, H2OWhich of the following statements best describes the stereospecificity of the resultingproduct of oxidation of an alkene using KmNO4? *Hydroxyl groups are found on opposite side.Alcohol groups undergo bond rotation.Alcohol groups are transformed into acids.Hydroxyl groups are found on the same side.What is the expected product from the hydrohalogenation of hex-1-ene using HCl? *1-chlorohexane1-chlorohex-1-ene1,2-dichlorohexane2-chlorohexane4. What are the products obtained from the following elimination reaction? Indicate the major product. CH3 CH,CH,ČCH, H2O 5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. CH;CH,CH,CH,CCH, Br b) For the major elimination product obtained in 5a), which stereoisomer (cis or trans) is obtained in greater yield? Draw the two isomers and provide the names of the compounds.
- For each reaction, decide whether substitution or elimination (or both) is possible, andpredict the products you expect. Label the major products. chlorocyclohexane + NaOC(CH3)3 in (CH3)3COHWhich of the following alkenes reacts fastest with HCl? 2-methyl-1-butene 3-methyl-1-butene 2-butene 1-buteneGive the major product of the following Grignard reaction: Br + Mg Ether What is the major addition product for the following reaction? CH3 CH3–CH2–C=CH2 + HBr H₂O₂
- H3C CH3 H3C NA C→XT Br Br₂ CH₂Cl₂ H3C Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂. CH3 Br In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br CH3 H3C CH3Which of the following compounds would not be a product of the reaction of 2-bromo-3-methylpentane in ethanol? (Ethoxy = -OCH2CH3) 3-methylpent-1-ene 2-ethoxy-3-methylpentane 1-ethoxy-3-methylpentane 3-methylpent-2-ene 2-ethylbut-1-ene4. Draw the structure of the four allylic halides formed when 3-methylcyclohexene undergoes allylic halogenation with NBS + hv. CH3 Allylic Bromination