Reactions of Alkenes Part 3

46) Provide the structure of the major organic product of the reaction below. Answer: 47) Provide the reagents necessary to convert 3-methyl-2-butanol to 2-methyl-2-butanol. Answer: 1. conc. H2SO4 2. H3O+ or Hg(OAc)2, H2O followed by NaBH4 or 1. PBr3 2. NaOCH3, CH3OH 2. H3O+ or Hg(OAc)2, H2O followed by NaBH4 48) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 49) Treatment of 2-methylpropene with which of the following reaction conditions results in an anti-Markovnikov addition product? A) dry gaseous HBr with peroxides present B) BH3-THF, followed by alkaline H2O2 C) aqueous Hg(OAc)2, followed by alkaline NaBH4 D) dilute H2SO4 and heat E) both A and B Answer: E 50) Both (E)- and (Z)-hex-3-ene can be subjected to a hydroboration-oxidation sequence. How are the products from these two reactions related to each other? A) The (E)- and (Z)-isomers generate the same products but in differing amounts. B) The (E)- and (Z)-isomers generate the same products in exactly the same amounts. C) The products of the two isomers are related as constitutional isomers. D) The products of the two isomers are related as diastereomers. E) The products of the two isomers are not structurally related. Answer: B 51) Provide the structure of the major organic product of the reaction below. Answer: 52) Provide the structure of the major organic product of the reaction below. Answer: 53) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 54) Complete the following reaction by filling in the appropriate reagents. Answer: 55) Provide the reagents necessary to complete the following transformation. A) 1. BH3∙THF 2. H2O2, HOB) H2O, H2SO4 C) OsO4, H2O2 D) CH3CO3H E) 1. CH3CO3H 2. H+, H2O Answer: A 56) Provide the structure of the major organic product of the reaction below. Answer: 57) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 58) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 59) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. (Z)-3-hexene Answer: → 60) Draw a structure for the transition state of the following reaction. Include correct partial charges. Answer: 61) Which of the following additions to alkenes occur(s) specifically in an anti fashion? A) hydroboration-oxidation B) addition of Br2 C) addition of H2 D) addition of H2O in dilute acid E) both A and B Answer: B 62) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 63) Complete the following reaction and provide a detailed, step-by-step mechanism for the process. Answer: 64) Addition of Br2 to (E)-hex-3-ene produces ________. A) a meso dibromide B) a mixture of enantiomeric dibromides which is optically active C) a mixture of enantiomeric dibromides which is optically inactive D) (Z)-3,4-dibromo-3-hexene E) (E)-3,4-dibromo-3-hexene Answer: A 65) Which of the following alkenes will yield a meso dihalide when reacted with Br 2/CCl4 at room temperature? A) B) C) D) E) both Band D Answer: B 66) Provide the major organic product of the reaction below. Answer: 67) Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 68) Provide a detailed, step-by-step mechanism for the reaction shown below. Answer: 69) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 70) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 71) Consider how the ICl bond is polarized and predict the product which results when this mixed halogen adds to 1-methylcyclohexene. Answer: 72) Provide the structure of the major organic product of the reaction below. Answer: