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Rec_5key - Recitation Problem Set#5 CHEM lSZL 2H 2.50 8 3...

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Unformatted text preview: Recitation Problem Set #5 CHEM lSZL 2H 2.50 8 3) Rank the following anilines in order of decreasing basicity: NH» 4 cho NH2 \@/ ond; i.” lea 53f- Br NH2 4) Show how the following cornpounds could be synthesized from benzene: a) m-chlorobezenesulfonic acid b) benzyl alcohol 0) l-phenyipentane d) m-bromobenzoic acid 5) Which of the following compounds will react with HBr more rapidly? . M01 glaloilwcg / \Hj/j Caloocahm NH; ”km—($10961 Recitation Problem Set #5 CHEM 152L 2/12/08 1) p-fluoronitrobenzene is more reactive than p-chloronitrobenzene toward hydroxide ion. What does this tell you about the rate determining step of nucleophilic aromatic substitution? ‘L C _ F 1 ( A}! \F/ Mac 8+ Ever \nOoQ/ ‘73 Max 2 / (a r’“ C\/uss 3* ‘0‘“ {MW E] £0 QD% l 3 N07.. (1%,;ch or? hate) a+ MO’L 9+ W h) LVC‘KL (“CA bend 2) The following tertiary alkyl bromides undergo an SNI reaction in aqueous acetone to form the corresponding tertiary alcohols. List the alkyl bromides in order of decreasing reactivity Recitation Problem Set #5 CHEM 152L 2/12/08 SQSH $039: \ “ W q” (1 a ‘2 fag-«EL? o (E fiafiaér O SRLCKB ._.__ (A \/ r C,“ D“? C“) C623 %OP 2 \ QfiaLK /\\ 983/0 \/_‘ fm‘gf Q b\ C) «was? 0 PM”? —~ \ 0 (\{N \ W Av 24% K g/NC‘» E? ”:7 o a Q\ \ ‘\ ago "” PM 5 ’5 —~(“ ...
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