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exam2_key - 322b Fall 2011 - Exam II Review Sheet — Cha...

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Unformatted text preview: 322b Fall 2011 - Exam II Review Sheet — Cha ter 15 Note: Assignment #2 serves as the Chapter 14 review sheet for Exam II 1. Multiple Choice. 1. The order of reactivity (fastest to slowest), ignoring the position of substitution, among the aromatics below in nitration is: OH CI CH3 II III I\I lI>IV>lll>I lV>II>lII>I f H>IV>I>IH , wgamwsmwwwwv“ 1 IV>ll>l>lll 2. Among the monosubstituted benzenes below, the ortho/para products will '- ' Weatmwénmwvz tau—.an sat—1:: dominate wit : C) ,_ s 5‘ CN HN/l\ 0 efo a {\x “" I II III IV at": ', LlH,andIV II and III III and IV M? K9,} a. u 33:; a 3. An 5N1 reaction will proceed slowest with which p-substituted benzyl bromide? Circle the functional group below. Y ____SL__, Br -CH3 -C| 4. Circle the structure or structures below that are effective electrophiles for the electrophilic aromatic substitution on benzene itself. OQSl/O Br-Br 5. Circle the compound or compound that would react in a Friedel—Crafts reaction to give a substitution product. . - 0 if CI 3% N H 2 C F3 6. Circle the reactive intermediate (1 or II) in each pair that is more stable. /@ <9 i g or 1. X a; \\\i/ H 11. Complete the Reaction. C(CH3)3 0 + excess Compound A 10. Give the major tri-substituted benzene product(s). (The product or products will have three substituents on the benzene ring). : 0:2 —-———> CN FeC|3 11. 12. 13. OH OCH3 Li, NH3, CH3CH20H -——————————> -33 0C O \Jk AICI3 (1 eq) 1. ——————————-——> 2. H30“ OH $0! + Q 1.AICI3 ON 2. H30+ 15. NH2 0 CH36CI | G OH excess AICI3 III. Mechanisms. 16. Draw the complete “electron-pushing" reaction mechanism for the transformation below. OCH3 OCH3 Cl C, CI + A wflgl3_._> 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. ooH3 “30 HF + M —————-——-———> Product 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. ©“—+ 0' ————————> ...
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exam2_key - 322b Fall 2011 - Exam II Review Sheet — Cha...

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