Organic Chemistry 2 – CHM 2211
Practice Problems

|1. |What is the product, A, that would be obtained from the following reaction sequence? |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |V |

|2. |Your task is to synthesize 2-phenyl-2-hexanol through a Grignard synthesis. Which pair(s) of compounds listed below would you |
| |choose as starting materials? |
|A) |[pic] |
|B) |[pic] |
|C) |[pic] |
|D) |Answers A) or B) |
|E) |Answers A) or C) |

|3. |Which of the following would be a reasonable synthesis of CH3CH2CH2CH2OH? |
|A) |[pic] |
|B) |[pic] |
|C) |[pic] |
|D) |More than one of these |
|E) |None of these |

|4. |Epoxidation followed by reaction with aqueous base converts cyclopentene into which of these? |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |Equal amounts of III and IV |

|5. |When nucleophilic addition to a carbonyl group occurs, the carbon attacked undergoes this hybridization change: |
|A) |sp2 ⎯⎯⎯⎯→ sp3 |
|B) |sp ⎯⎯⎯⎯→ sp2 |
|C) |sp ⎯⎯⎯⎯→ sp3 |
|D) |sp3 ⎯⎯⎯⎯→ sp2 |
|E) |sp2 ⎯⎯⎯⎯→ sp |

|6. |What is the electrophilic species involved in the initial step of the reaction below? |
| | |
| |[pic] |
|A) |+OH |
|B) |+HgOAc |
|C) |H3O+ |
|D) |THF |
|E) |the THF/H2O complex |

|7. |Which of these ethers is least likely to undergo significant cleavage by hot aqueous H2SO4 ? |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |V |

|8. |A correct IUPAC name for [pic] is: |
|A) |2-Ethyl-4-pentanol |
|B) |4-Ethyl-2-pentanol |
|C) |3-Methyl-5-pentanol |
|D) |5-Methyl-2-hexanol |
|E) |4-Methyl-2-hexanol |

|9. |Select the structure of the major product formed in the following reaction. |
| |[pic] |
|A) |CH3CH2CH218OH |
|B) |[pic] |
|C) |[pic] |
|D) |[pic] |
|E) |[pic] |

|10. |The product(s) of the following reaction |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |None of these |

|11. |Which pair does not represent a pair of resonance structures? |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |All of these represent pairs of resonance structures. |

|12. |Which compound (or compounds) would be produced when trans-2-butene is treated first with a peroxy acid to form an epoxide, and |
| |then the epoxide is subjected to acid-catalyzed hydrolysis? |
| | |
| |[pic] |
|A) |An equimolar mixture of I and II |
|B) |An equimolar mixture of II and III |
|C) |I alone |
|D) |II alone |
|E) |III alone |

|13. |What would be the final product? |
| |[pic] |
|A) |(CH3)2CHCH2OCH3 |
|B) |[pic] |
|C) |[pic] |
|D) |[pic] |
|E) |[pic] |

|14. |What would be the major product of the following reaction? |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |An equimolar mixture of I and II |

|15. |The following reaction, |
| |[pic] |
| |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. |

|16. |What is the major product of the reaction: |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |Both III and IV |

|17. |What would be the product, O, of the following reaction sequence? |
| | |
| |[pic] |
|A) |CH3CH2CH2CH3 |
|B) |[pic] |
|C) |[pic] |
|D) |CH3CH2CH2CH2OD |
|E) |CH3CH2CH2CH2D |

|18. |Which of these reactions will not produce a 1° alcohol? |
|A) |[pic] |
|B) |[pic] |
|C) |[pic] |
|D) |[pic] |
|E) |[pic] |

|19. |Which is the best method to prepare tert-butyl methyl ether? |
|A) |CH3ONa + (CH3)3CBr |
|B) |CH3ONa + (CH3)2CHCH2Br |
|C) |CH3OH + H2SO4; then (CH3)2C=CH2 |
|D) |CH3OH + (CH3)3CBr |
|E) |CH3OH + (CH3)3COH + H2SO4, 140°C |

|20. |The correct IUPAC substitutive name for [pic] is: |
|A) |4-Penten-2-methyl-2-ol |
|B) |4-Methyl-1-penten-2-ol |
|C) |2-Methyl-4-penten-2-ol |
|D) |4-Methyl-1-penten-4-ol |
|E) |4-Hydroxy-4-methyl-1-pentene |

|21. |Which statement is true concerning the formation of alcohols by the hydroboration-oxidation sequence? |
|A) |Overall, the process results in syn addition and anti-Markovnikov orientation. |
|B) |Overall, the process results in anti addition and anti-Markovnikov orientation. |
|C) |Overall, the process results in syn addition and Markovnikov orientation. |
|D) |Overall, the process results in anti addition and Markovnikov orientation. |
|E) |The stereochemistry and orientation are unpredictable. |

|22. |How many ethers with the formula C4H10O are possible? |
|A) |1 |
|B) |2 |
|C) |3 |
|D) |4 |
|E) |5 |

|23. |What is the product of the reaction of propyl alcohol with (CH3)3SiCl in the presence of a tertiary amine. |
|A) |CH3CH2CH2Si(CH3)3 |
|B) |(CH3)2CHSi(CH3)3 |
|C) |CH3CH2CH2OSi(CH3)3 |
|D) |(CH3)2CHOSi(CH3)3 |
|E) |(CH3CH2CH2)3SiOH |

|24. |Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same |
| |molecular weight.) |
|A) |CH3CH2CH2CH2CH3 |
|B) |CH3CH2CH2CH2OH |
|C) |CH3CH2CH2OCH3 |
|D) |CH3CH2CH2Cl |
|E) |CH3CH2OCH2CH3 |

|25. |Which of these alkyl halide syntheses is predicted to occur at the greatest rate? |
|A) |CH3CH2CH2CH2OH + HI ⎯⎯⎯⎯→ |
|B) |(CH3)2CHCH2OH + HBr ⎯⎯⎯⎯→ |
|C) |[pic] |
|D) |[pic] |
|E) |(CH3)3COH + HI ⎯⎯⎯⎯→ |

|26. |Which of these compounds will not be reduced by LiAlH4? |
|A) |CH3CH2CH2CH=CH2 |
|B) |[pic] |
|C) |[pic] |
|D) |[pic] |
|E) |[pic] |

|27. |The final product, D, in the following reaction sequence, |
| | |
| |[pic] , would be? |
|A) |[pic] |
|B) |[pic] |
|C) |[pic] |
|D) |[pic] |
|E) |[pic] |

|28. |The correct structure for benzyl alcohol is: |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |V |

|29. |Select the correct reagent(s) for the following reaction: |
| | |
| |[pic] |
|A) |LiAlH4/ether; then H3O+ |
|B) |NaBH4; then H3O+ |
|C) |H2 with Pt/C |
|D) |A) and B) |
|E) |A), B) and C) |

|30. |Which of these is the most accurate name for the molecule |
| |[pic] |
|A) |sec-Butyl phenyl ether |
|B) |Isobutyl phenyl ether |
|C) |tert-Butyl phenyl ether |
|D) |(R)-2-Phenoxybutane |
|E) |(S)-2-Phenoxybutane |

|31. |Which compound is a tosylate? |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |V |

|32. |A correct IUPAC name for isobutyl alcohol is: |
|A) |2-Methyl-1-propanol |
|B) |2-Methyl-1-butanol |
|C) |1-Methyl-1-propanol |
|D) |1,1-Dimethyl-1-ethanol |
|E) |3-Methyl-1-propanol |

|33. |The product, B, of the following reaction, |
| |[pic] |
| |would be: |
|A) |[pic] |
|B) |[pic] |
|C) |[pic] |
|D) |[pic] |
|E) |[pic] |

|34. |Which of the following dienes is a cumulated diene? |
|A) |CH2=CHCH2CH2CH=CH2 |
|B) |CH2=CHCH=CHCH2CH3 |
|C) |CH3CH=C=CHCH2CH3 |
|D) |CH3CH=CHCH=CHCH3 |
|E) |CH3CH=CHCH2CH=CH2 |

|35. |Which would be the major product of the reaction shown? |
| | |
| |[pic] |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |V |

|36. |Which synthesis of a Grignard reagent would fail to occur as written? |
|A) |[pic] |
|B) |[pic] |
|C) |[pic] |
|D) |[pic] |
|E) |All of the above will succeed. |

|37. |Which carbon-carbon bond in the following compound would you expect to be longest? |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |V |

|38. |Which of the following reagents might serve as the basis for a simple chemical test that would distinguish between CH3CH=CHCH3 |
| |and [pic] |
|A) |CrO3 in H2SO4 |
|B) |Dilute aqueous KMnO4 |
|C) |Br2 in CCl4 |
|D) |Two of these |
|E) |All of these |

|39. |Select the structure of benzyl methyl ether. |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |IV |
|E) |V |

|40. |The major product of the following reaction would be: |
| | |
| |[pic] |
|A) |I |
|B) |II |
|C) |III |
|D) |Equal amounts of I and II |
|E) |None of these |

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