Quiz 4 - Quiz 4 Chem 1093 NOTE 0D hoods are stronger than...

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Unformatted text preview: Quiz 4 Chem 1093 NOTE: 0D hoods are stronger than C-H honds....ie. harder to break. This is a very usefoi fact to know in some ofthe foltowing questions. i. Which ofthc foilowing would you expect to react fastest with the nucteophite I" (iodide)? 5 A) CHJCE'szHzBI B) CHgCHzCHzCi C) {CH3}1CHCHzBr D) (CHflzCHCHgCi r E) (CH3}3CC32EI . ifthe concentration ofNaOH is doubled in the fotiowittg reaction, what witl' happen to the reaction rate? 2. Predict the M339 3 product IF the following reaction went by the SN! pathway: (3151;: [A] A) nochange ——" "‘ a} doubtc C) quadruple D) cut in hatf E) none of these 9 A) 02cc”: 6. What wouiti be the major organic product of the foliowittg reaction? 9 K' new“ ,1. B) (MICK; _ GHZCI ? i-EOCtCHfls C? C) O’Cfiaootcnm A} 020C113 6 Ha D) a, O<°°<Wa on; Q E) C) CH; 3. Indicate thé cxpcctcdmmwoduot of the foliowing reaction: 9) or; E) 7. What woutd be tho major organic product of the fotiowing reaction? 9.“: 1"“): Ctlp‘Na‘ CM hm»? B! ‘ 0E! CH3. C3} CH I it “ m, \ _ A) CD; CH; 9} mt . a ’co, b\ * cm a} com CH; 0 cm ‘ ,\\ca3 6. Q \ A) ‘ £11.: c) OOH; Um cf/CDI‘ \ D) C“: D) < >"" OH: cu; * cu, (I; #69, \ (tttcemic) E) C“ J E) 06',“ 4 The M18193 product of the foliowing reaction conditions wiil result from: 8, Which would be true oftitr: following reactions? 7GB" K' "cacao; X0 21' Ducts}, -“"’ cit tram A) SN: . . __ 7 . , ‘ , B} 8:41 C) 52 A) ctswoutd react faster D} E1 B) {mm woutd react faster E) mm is no my to know C) cts and Imus woutd react at the same rates D) no reaction is expected undo: these conditions E) the product shown would not be formed 9‘ What major product would result for the following minim"? 13. Which ofmc following nzoiocuies WILL, readily undergo an elimination reaction when treated with NaOCH;? ammo- :v ? mm CII3CI‘130i-i D ; 0* D) E) None of these would undergo elimination. A) H H D B) D H 14. Which mechanism proceeds with invasion of configuration? H g! A) bimoiecuiar elimination (52) ' WM": 8) unimolocuior eiimination (at) o C) unimoiecular substitution (Sui) D ' D) bimoieoular substitution (5N2) C) E} flee-radios! haiogenation H t! H ‘ Game“: 15. Which of the cyciohoxyi bromides would you expect to react the fastest in the foliowing reaction? toxemia] D) D . . . H aikyi bromide M... “r H H mum: H a) 0- Br . H it}. Which of the haioaikanos below would you expect to most tapidiy undergo the reactants H D shown? A) H ":0 Br RX --—~—*—-—h- ROH + HX H U Rectono B] H A) CH3CHgBr B} (3135: B! C) (CH3)3CBE D} CHgCHBrCHs V H 8: . H H E G, C) O ) a: H. Which oftito bases below would be best to accomplish the following reaction? H H D D) H E) ail would react at this some. Into :6. Predict tho MAJOR product of tho foiiow‘mg 8N1 reaction: ‘9 Q ————-—' Q ' cHQ'quIF'C‘HIB! CR:“CH=CH3 A} {3530'1‘13‘t B) Ci‘hcl‘lzCT'i‘itt+ C} {CHfigCHO' Na+ D) {CHahCO‘ Na“ E) No+‘OH 12. What wouid be the major product of the foiiowing reaction? ~ 9‘ Ron I . GHQ—CHz-CH-CHg W ., \ m H/cmc\e A] "‘3 GH ' I 3) CH3“ CH3 "‘ CH-CH; ph gEt 14“ /H " c _c C) mo” ~"an, 5’) 9) CH, - CH, - CH: CH, 0 3« ll anaemic E) carom-own; E) Ph heat ' {K H30 [H ‘ 33} F: i7. Which one ofthe following wouEd undergo 52 elimination most rapidly? 9) B) All would react at the some late 18. Which of the nucleophilcs shown below wouitl NOT cause an E2 elimination as the predominant reaction? 3) common (2) "CN 5) ‘OH E) cu,o-_ $9. How many atkeno products are gossible in the foliowing reaction? A) None; cannot eliminate B) One C) Two D} Three 5) Four 20. Predict the product of reaction of the foliowing deuteratcd compound. A) ll "' 'Cth il 8) l) CH3. 2 l. To which side (irony) would the following equilibrium lie? tilt“ “36‘ Flo-0' N3 + E-tzfl <--—" Flt-OH 4 53:10“ INC. ch A) To the lofi B) To the right C) Equally to the right and Eeft D} There is no way to tetl E) This reaction cannot occur at alt 22. What is the Moment of the following reaction: l~pelilaatol CH5“ A) B) C} D) E} 23. Rank the following alcohols in order oftiecreaslng acidity in solution. CI {5.0" (‘IIJCI I20" {(313361 a)" {Cgijhcou l _ 3 3 u! A) l>2>3>4 B) 2>l>3>4 Ct 4>3>2>t D) 4>3>l>2 E) E>3>2>4 24. Which oftho foitowlng reactions would be the best for the preparation ofanisole (methoxybenzene)? '3' (1130' No‘ ----———y- '1" A) 0" canon W l B) “2504 0' “8 costs: mum—J» ? C} 0 i. CHJMgEr W 1! D) 2. H 50' E) None of those would work”. 25. Saytzev's Rute has to do with the following: A} Free-radical substimtioos B} Hydration of double bonds C) Bromination of double bonds D) Products of elimination reactions 13) Hydrogenation of double bonds 26. Which otthe following can be used to synthesize. (R)»2-cyanopentatte from (R)-2~hromopemane? A) Nata: B) NaCN C) Nat followed by KCN D) NoCN followed by Hi ‘5.) This reaction cannot occur 27. 3N2 substitution at secondary halides and sulfonetes is ofien complicated by competing 33' Wthh 0”“ f°H°Wlflg is not normally 3 ENE] leaving Em“? 0" carbon? E2 elimination. Which of the nucleophilcs below would you choose to obtain the highest A) Bl” yield in an 8N2 reaction with menthyl bromide? 3) QCH3 C) C! D) 05023 E): 34. To which side (irony) would the followiug equilibrium lie? + non _._...——** amongst: -+ KO“ A} CH30Na A) m the left 8) CH3C02Na B) to the right C) ((31th C} equally to the right and left D) (CH3)3C0K B} there is no waytotell E) CGHSSNa E) only 3N2, Em and E2 reactions are possible 28. What is the correct stercochemistry of the product of the following reaction: 35' predict the major pmdmt offlm knowing reaction: excess NaCN M N I'll é A) H “1 i‘h A) 3R,4S N? H a) 28.312 B) C) 211.33 II D) 212.31: mm B) 312,452 c) . N3 29. Wliiéh of the following is the best leaving group? Q: {'11 u 6 D) A)‘ I E} no reaction occurs a} awn” 36. Which ofthe following haloalkanes wwid not undergo the reaction below? “0‘9 C) r9 A) (cameo! D) . B) mile: a C) (CH3)3CBr CELLO D) CH3CHzBr E) E} Cflacl'hcfizE 30. Which of the following reagents wouiti best accomplish a typical 5N2 reaction? A) cogoo 3} 33,0 C) HCN D) KEN E} KO‘Bu 31. Predict the wafer product otthe following reaction: Br Matt; 9 (13 @243 Ci C" m G E) no reaction occurs A} B) C} 32. Several aikyl halides. including iodometliane, are known carcinogens or cancer-suspect materials. To destroy these materials by conversion to non—electrophilio species, you can react them with aucleophilea. Which of the following would be the best For rapidly destroying methyl iodide {iodomethane}? A} CH30H i3) NH; C) H20 D} Nat E) Cchozfi /’ ...
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