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exam2_blank - 1 322b Fall 2011  Exam II Review...

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Unformatted text preview: 1 322b Fall 2011  Exam II Review Sheet – Chapter 15 Note: Assignment #2 serves as the Chapter 14 review sheet for Exam II I. Multiple Choice. 1. The order of reactivity (fastest to slowest), ignoring the position of substitution, among the aromatics below in nitration is: OH Cl CH3 I II III IV II > IV > III > I IV > II > III > I II > IV > I > III IV > II > I > III 2. Among the monosubstituted benzenes below, the ortho/para products will dominate with: O O HN CN I II I, III, and IV II and III III and IV III only III IV 2 3. An SN1 reaction will proceed slowest with which p ­substituted benzyl bromide? Circle the functional group below. SN1 Y Br - CH3 - Cl Y= -OCH3 - CF 3 4. Circle the structure or structures below that are effective electrophiles for the electrophilic aromatic substitution on benzene itself. ONO O S O Br-Br 5. Circle the compound or compound that would react in a Friedel ­Crafts reaction to give a substitution product. Cl CF 3 NH2 O 3 6. Circle the reactive intermediate (I or II) in each pair that is more stable. or I II or I II. II Complete the Reaction. 7. C(CH3)3 + excess (CH3)3COH 4 8. NH2 NH2 NH2 Br + Br 9. Compound A NO 2 Compound A Br 10. Give the major tri ­substituted benzene product(s). (The product or products will have three substituents on the benzene ring). Cl Cl 2 CN FeCl3 5 11. O OH Li, NH3, CH3CH2OH -33 oC O CH3 12. O AlCl3 (1 eq) 1. 2. H3O+ 13. O O OH 6 14. O Cl + 1. AlCl3 2. H3O+ O2N 15. NH2 O C H 3C C l OH excess AlCl3 7 III. Mechanisms. 16. Draw the complete “electron ­pushing” reaction mechanism for the transformation below. O CH3 O CH3 Cl Cl Cl AlCl3 + CH3 CH3 8 17. Draw the complete “electron ­pushing” reaction mechanism for the transformation below and draw the structure of the product. There is one major product in this reaction. O CH3 H3C HF + CH3 Product 9 IV. Synthesis. 18. Outline an efficient synthesis for the compound below using the indicated starting material and any one or two carbon compounds as the only carbon sources (note that HCOCl is not an acceptable carbon source). HO 10 19. Outline an efficient synthesis for the product below using the indicated starting material and any compound of 2 carbons or fewer as the only carbon sources. Cl O ...
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