322b_09fall_sample_lab_quiz1

322b_09fall_sample_lab_quiz1 - CHEMISTRY 322bL NAME Lab time

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Unformatted text preview: CHEMISTRY 322bL NAME Lab time ._______________________ T.A. This test comprises this sheet and five numbered pages. 3M5 Len/"C ‘5??? #1; F0? 1. (7) Recall the Grignard synthesis of 2—methyl-2-hexanol, CH3(CH2)3C(OH)(CH3)2, from n«BuBr and acetone, CH3COCH3. (a)(3) A Grignard reaction mixture includes a little 12. State two behaviors one observes if the reaction starts rapidly without external heating. Use < 12 words total. (b)(2) If the addition of noBu~Br is too fast, a large amount of the "cOupling side product“ forms. Write a balanced equation for its formation and give the product's structure. (c)(2) Tell why the aq soln used to convert the Grignard/acetone adduct to the product should be cold, dilute, and only weakly acidic. Use <10 words. 2. (7) Recall the Period 2 alkylation of anisole, Ph-OMe, by Ph3COH in HOAc with catalytic H2504 to give p—MeO-CSH4—CPh3. (a)(2) Put "rev(ersible)" or I'ixnrueverssible)" in each blank: The rxn fails in Eton because its rxn with Ph3C+ is . The prep as done succeeded because rxn of 9113C+ with HOAc is , and its rxn with anisole is .__*~.__*_____. (b)(5) Given ratio Desired Prod to Side Prod is 50:1 at 20°, 1:1 at 80°, and is exponential in ALT: Calculate T (3 sig figs) to give DP:SP a 10:1. In defining AkT, note that DP:SP goes up as T goes down. Show calculation; OK to take 109105 a 0.70. d8; recall t the aq p ase is nearly 1:1 M s-emul‘u‘r I! 3 «M! Ma? 620:: 652,36 Y +22) flracfr‘u. fiat" you! ‘7 "ng; .' 4. (5) For drying by distillation of dilute W solns in an OS: Given y a amt W, x a amt pot soln, and r a the vapor-to-liquid W conc ratio, ln(y/yo) a r[1n(x/xo)]. For r a 10, calculate the fraction or the soln one must distill, fd (3 1 ~ (x/x to distill 90% of the Water, i.e., to make (y/yo) a 0.10. wd/ MIL @474 0‘“ W 0)): 5. (2) For 1A418+1C: Exactl solution containing B. Reaction of 10 pure C. Calculate the 8 yield of C based A. * 312% Pm LQ 135/;~ (‘09 GEL Lee/j 6. (6) Recall the isatin/acetophenone aldol condensation: 3 C33.C‘Ph Isatin Acetophenone MW a 147; mp a 193—195“ MW a 120; d a 1.03 (a) Draw the structure of cpd I, (b) Calculate the MW of cpd I sol relationship to the starting materials; show calculation. (c) When the (nearly) colorless soln of cpd I is warmed with aq/alc HCl, the soln turns deep red, producing cpd II. In < 12 words, tell what electronic structural change is occurring. the initial aldol product. ely from its stoichiometric 7. (5) Consider the reaction below: A + B——-—-—--—-—’- C + D [initial] 1.0 10.0 0 0 [equilibrium] 1 - x lo « x x x (a)(2) Calculate [Aleq for Reg 3 4.00. To simplify the calculation, take x - 1.0 in all terms except 1 ~ x, then solve for x. (b)(3) Tell what the calculation means, given that only A is hard to separate from products. (the that if [Ali a [Eli then [C]eq a [meg = 2/3mi, and {Meg = 1/3[A]i.} flu Wm 1—? #1 5‘37 (fl La!) 8. (9) Recall the methyl benzoate prep as done. PhCOOH + 16 9 HOME -—~—-—--—~dh- PhCOOMe + HOH M MW 3 122 MW I 32 MW 8 98 MW 3 135 hp a 199° quation(e) and < 20 words, Na2CO3 extracted PhCOOH, but not the ester, from the DCM (CHZClz) solution containing both. (c)(2) Droplets of aq N32c03 were just before distillation. 8.1mm- on the drawing below. (2) In must be fast for benzoin pro- duction to be efficient. (write struc ~-‘->) , is produced as is W. reduced to Cu‘. In (re)oxidizing 2 Cu‘, NH NO (in excess) is 4 3 reduced to NH4N02, which decomposes to ._____~___ gas and water. One path to N02” 13 reduction of . «N02 angaaza only after rxn is there is nothing left to reduce the brown gas 'NOZ by complete because then - M basic gas, a one-carbon dianion Ph ph_\c._...«° Hfi, Kn: \/ O ...
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This note was uploaded on 10/20/2009 for the course CHEM 322BL at USC.

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322b_09fall_sample_lab_quiz1 - CHEMISTRY 322bL NAME Lab time

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