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SCI2199 - Introduction to Organic Chemistry II - Fall 2016 Homework 2 _______________________________________________________________________ 1. Which of the following could not be used to synthesize 2-bromopentane efficiently? A) 1-Pentene + HBr → B) 2-Pentene + HBr → C) 2-Pentanol + HBr → D) 2-Pentanol + PBr3 → E) All of these choices would afford good yields of 2-bromopentane. 2. trans-3-Methylcyclopentanol is treated with CH3SO2Cl in the presence of base. The product of this reaction is then heated with KI in methanol. What is the final product? A) trans-1-Iodo-3-methylcyclopentane B) cis-1-Iodo-3-methylcyclopentane C) 1-Methylcyclopentene D) 2-Methylcyclopentene E) 3-Methylcyclopentene 3. What would be the major product of the following reaction sequence? A) B) C) D) E) I II III IV An equimolar mixture of I and II. Page 1 4. What would be the major product of the following reaction sequence? A) B) C) D) E) I II III IV An equimolar mixture of I and II. 5. Which of the following could be used to synthesize 1-bromopentane? A) CH3CH2CH2CH=CH2 + HBr → B) CH3CH2CH2CH2CH2OH + PBr3 → C) CH3CH2CH2CH2CH2OH + NaBr → D) CH3CH2CH2CH2CH2OH + Br2 → E) CH3CH2CH2CH=CH2 + Br2 → 6. What would be the major product of the following reaction sequence? A) B) C) D) E) I II III IV An equimolar mixture of I and II. Page 2 7. Which of the following could be used to synthesize 2-bromobutane? A) CH3CH2CH=CH2 + Br2(aq) → B) CH3CH2CHOHCH3 + HBr → C) CH3CH2C≡CH + HBr → D) CH3CH2C≡CH + Br2 → E) More than one of these choices. 8. Which of the alcohols listed below would you expect to react most rapidly with PBr3? A) CH3CH2CH2CH2CH2CH2OH B) (CH3CH2)2CH(OH)CH2CH3 C) (CH3CH2)2CHOHCH3 D) (CH3CH2)3COH E) (CH3CH2)2C(CH3)OH 9. cis-3-Methylcyclopentanol is treated with CH3SO2Cl in the presence of a base. The product of the reaction then is allowed to react with KI in methanol. What is the final product? A) trans-1-Iodo-3-methylcyclopentane B) cis-1-Iodo-3-methylcyclopentane C) 1-Methylcyclopentene D) 2-Methylcyclopentene E) 3-Methylcyclopentene 10. The reaction between 4-methyl-1-pentanol and PBr3 to yield 1-bromo-4methylpentane is probably: A) an SN1-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. B) an SN2-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. C) an E1-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. D) an E2-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. E) an epoxidation reaction. Page 3 11. Which compound is a mesylate? A) B) C) D) E) I II III IV V 12. The reaction between 2-methyl-2-pentanol and HBr to yield 2-bromo-2methylpentane is probably: A) an SN1-type reaction involving the protonated alcohol as the substrate. B) an SN2-type reaction involving the protonated alcohol as the substrate. C) an E1-type reaction involving the protonated alcohol as the substrate. D) an E2-type reaction involving the protonated alcohol as the substrate. E) an epoxidation reaction. 13. Which alcohol would undergo acid-catalyzed dehydration most rapidly? A) 3,3-dimethyl-1-butanol B) 2,2-dimethyl-1-butanol C) 3,3-dimethyl-2-butanol D) 2-methyl-2-butanol E) All would undergo dehydration equally rapidly. Page 4 14. What would be the major product of the following reaction sequence? A) B) C) D) E) I II III IV An equimolar mixture of I and II. 15. Which reagent(s) would transform propyl alcohol into propyl bromide? A) Concd. HBr and heat B) PBr3 C) NaBr/H2O and heat D) More than one of these choices. E) All of these choices. Page 5 16. What would be the major product of the following reaction sequence? A) B) C) D) E) I II III IV An equimolar mixture of II and III. 17. Which of the following could be used to synthesize 2-bromobutane? A) B) C) D) E) More than one of these choices. 18. The reaction between 1-pentanol and HBr to yield 1-bromopentanol is probably: A) an SN1-type reaction involving the protonated alcohol as the substrate. B) an SN2-type reaction involving the protonated alcohol as the substrate. C) an E1-type reaction involving the protonated alcohol as the substrate. D) an E2-type reaction involving the protonated alcohol as the substrate. E) an epoxidation reaction. Page 6 19. Which of the alcohols listed below would you expect to react most rapidly with HBr, assuming the reaction pathway is predominantly SN1? A) CH3CH2CH2CH2CH2CH2OH B) (CH3CH2)2CH2CH2OH C) (CH3)2CHCH2CHOHCH3 D) CH3CH2CH2CH2CH2OH E) (CH3CH2)2C(CH3)OH 20. Which of the following could be used to synthesize 2-chlorobutane? A) B) C) D) E) None of these choices. 21. The reaction between 2-methyl-2-pentanol and HBr to yield 2-methyl-2-pentene is probably: A) an SN1-type reaction involving the protonated alcohol as the substrate. B) an SN2-type reaction involving the protonated alcohol as the substrate. C) an E1-type reaction involving the protonated alcohol as the substrate. D) an E2-type reaction involving the protonated alcohol as the substrate. E) an epoxidation reaction. 22. Which of the following could be used to synthesize 2-chlorobutane? A) CH3CH2CH=CH2 + Cl2(aq) → B) CH3CH2CHOHCH3 + HCl → C) CH3CH2C≡CH + HCl → D) CH3CH2C≡CH + Cl2 → E) None of these choices. Page 7 23. The conversion of is best achieved through use of which of these reagents in a low temperature reaction? A) Concd. HBr B) Br2 C) NaBr, H2SO4 D) PBr3 E) HBr, peroxide 24. Assuming the mechanistic pathway for each of the following reactions is predominately SN1, which of these alkyl halide syntheses is predicted to occur at the greatest rate? A) CH3CH2CH2CH2OH + HI → B) (CH3)2CHCH2OH + HBr → C) CH3CHOHCH2CH3 + HCl → D) CH3CHOHCH2CH3 + HBr → E) (CH3)3COH + HI → 25. Which of the following reactions would serve as a synthesis of butyl bromide? A) B) CH3CH2CH2CH2OH + PBr3 → C) D) CH3CH2CH2CH2OH + Br2 → E) Two of these choices. 26. The reaction between 4-methyl-1-pentanol and HBr to yield 4-methyl-1-pentene is probably: A) an SN1-type reaction involving the protonated alcohol as the substrate. B) an SN2-type reaction involving the protonated alcohol as the substrate. C) an E1-type reaction involving the protonated alcohol as the substrate. D) an E2-type reaction involving the protonated alcohol as the substrate. E) an epoxidation reaction. Page 8 27. Which compound is a tosylate? A) B) C) D) E) I II III IV V 28. The conversion of 3-methyl-1-octanol to 1-chloro-3-methyloctane is best achieved through use of which of these reagents? A) Concd. HCl B) SO2Cl2 C) NaCl, H2SO4 D) PCl3 E) POCl3 29. Which of the following could be used to synthesize 2-iodobutane? A) CH3CH2CH=CH2 + I2(aq) → B) CH3CH2CHOHCH3 + HI → C) CH3CH2C≡CH + HI → D) CH3CH2C≡CH + I2 → E) None of these choices. 30. Which of the following could be used to synthesize 1-bromobutane efficiently? A) CH3CH2CH=CH2 + HBr → B) CH3CH2CH2CH2OH + PBr3 → C) CH3CH2CH2(OH)CH3 + HBr → D) CH3CH2CH2CH2OH + Br2 → E) None of these choices. Page 9 31. The following reaction, is probably: A) an SN1-type reaction involving the protonated alcohol as the substrate. B) an SN2-type reaction involving the protonated alcohol as the substrate. C) an E1-type reaction involving the protonated alcohol as the substrate. D) an E2-type reaction involving the protonated alcohol as the substrate. E) an epoxidation reaction. Page 10