CHEM 31 PROBLEM SET: ORGANIC MECHANISMS - NUCLEOPHILICNAME: _________________________________ 1. Which one of the Grignard reactions below could give rise to CH3CH2CH(OH)CH2CH3? (A) (B) (C) (D) propanone and methyl Grignard butyl Grignard and acetaldehyde ethyl Grignard and propionaldehyde methyl ethyl ketone and methyl Grignard 2. Indicate the reagents and/or compounds required to carry out the transformation shown below: ? O 1,6-hexanedione SEC. _______________ SCORE: ____________ 5. What is the principal product of the following reaction? H+ O + 2 CH 3OH (A) (B) (C) (D) (E) 5,5-dimethyl pentanal cyclopentanone dimethyl ketal 3-methyl-1,5-pentanedione 2-methyl cyclopentanone cyclopentane dimethyl acetal 6. What is the major product of the reaction shown above? (A) H2O; H2SO4, heat; KMnO4; O3; Zn (B) LiAlH4; K2Cr2O7, H2O; NH2OH (C) LiAlH4; NaOH, heat; KMnO4 (D) H2O, H+; K2Cr2O7; NH2OH (E) LiAlH4; H2SO4, heat; O3; Zn 3. Which of the compounds below is the product of the following reaction? O C (CH2) 4CH3 H 2NNH 2 KOH heat OH CH (CH 2)3CH 3 (A) (CH2) 4CH3 (D) OH CH (CH 2)4CH 3 (B) (CH2) 5CH3 (E) OCH 2 (CH 2)4CH 3 (C) 4. Which of the following reactions will produce a secondary amine? 7. The saponification of the optically active ester using isotopically labeled oxygen as shown above would most likely produce which of the following products? LiAlH4 C.11. Which of the following structures is an intermediate formed in the amide hydrolysis shown above? 10. NaBH4 B. Which of the following is a product of the reaction sequence shown above? 12. Which of the following reactions would NOT be an acceptable method for the preparation of methyl benzoate? 14. H3O+ . What is the major product of the reaction shown above? 13. Of the following. which reacts with methylamine (CH3NH2) to form the imine shown above? 8. Which of these reagents can accomplish the following reaction? A. NaH D. Which of the following correctly indicates the order of reactivity of the halides above with sodium iodide in acetone? 9. 16-20: Determine the type of reaction: Choose : A. Free Radical Substitution F. conversion of allyl phenyl ether to o-allylphenol 19. oxymercuration of styrene 18. reduction of acetaldehyde by NaBH4 20. Claisen Condensation 21. Elimination G. Aldol Condensation D. OH. Electrophilic Addition E. HCl C6H5CH2CH3 22. C. Nucleophilic Substitution B. C6H5CH2CHO + Zn(Hg). D. B. 2 CH3CHO + KOH/H2O CH3CH(OH)CH2CHO 25. Clemmensen reduction B. PhCH2OH + HCOO23. PhCH2CH2CH3 24. CH3COOCH2CH3 + CH3CH2O-Na+ CH3COCH2COOCH2CH3 . Rearrangement 16. Electrophilic Substitution D. acid hydrolysis of acetonitrile 21-25: Identify the type of reaction: Choices: A. formation of hemiacetal 17. Nucleophilic Addition C. Cannizzaro reaction E. Which of the following is an intermediate formed in the reaction below? A. HCHO + PhCHO + OH.15. Wolf-Kishner reduction C. PhCOCH2CH3 + H2NNH2.