CHE128A Quiz 3-6 W07 Key Patten

CHE128A Quiz 3-6 W07 Key Patten - Student ID Name Chemistry...

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Unformatted text preview: Student ID #: Name: Chemistry 128A — Winter Quarter 2008 MWF 12: 10 am. — 1:00 pm. Dr. Timothy E. Patten Quiz #3 (30 Points), October 17, 2008 (E W 1. (6 Points) For 1,2-dichloroethane (shown), draw Newman projections for all staggered conformations formed by rotation about the C-C bond. Which staggered conformation(s) has (have) the lowest energy? Which has (have) the highest energy? Score: T T CI—‘C—C—CI ,, I l U C‘ (l H H H (X {k H "‘w/’ . : "I 1 DIG V H l (r H F) T f/v‘mo ’\ bum/x- 55 V" ' 2. (4 Points) Boat cyclohexane is higher in energy than chair cyclohexane by about 7 kcal / mole. List the two features of boat cyclohexane that contribute to this energy differqe2 e. 1) '1 \ ECL\95(r\/\r 5TYVMN {L ‘ j” *4 d1 / IV”, H "4 VU Q) 3. (6 Points) Draw both chair conformations (one chair conformation and its ring flipped conformation) of trans-4%:yclohexanol with equilibrium arrows in between the two. MM: 2) 57m“ ‘PFNNW (TMNxAN/x/utm) H ll 1 \~ O i \A/K\\,/\ \( ,3- fl \/—"—\/ < ("0; l H Name: Student ID #: 4. (5 Points) For the equilibrium as drawn in question 3, calculate the AG° for the conformational ring flip. Shown is the relevant table from your book. Group (AG° in kcal / mole) __ .- 5. (5 Points) List the following alkanes in order of increasing boiling point: 2— methylheptane, octane, and 2,2,4—trimethyl pentane. ‘ VA 2/ _, _ h . _ A - 2 2 \{,-1Mm=,\fi-\vtkffi«/\AN L L MEFMVA HUM/W“ é DC I Ar’lt l 6. (4 Points) List the following cycloalkanes in order of increasing ring strain: cyclobutane, cyclohexane, cyclopentane, cyclopropane. ‘ ‘ I . ~ — ‘ \/ ’\A’\L.flqul-\:\ "\J (LC/H E yams/1: L (gm; fit/xi) “NR 4 QYLLOGV. NW, C L LLVL' \ Student ID #: Name: MWF 12:10 am. — 1:00 pm. Chemistry 128A —- Winter Quarter 2008 Quiz #4 (30 Points), October 31, 2008 Dr. Timothy E. Patten (8 Points) Assign the priorities to the groups (1, 2, 3, and 4) in each set according to the 1. Cahn—Ingold-Prelog rules. (a) —H, -CH3, :27 —OH, [ —CHZOH 2 (b) —CH2CH=CH2, —CH=CH2, —CH3, -CH2C02H Q —CHZSH, 2. —NH3*, 1 -CH0 3 (C) —CH3 s (5 Points) The far left chemical structure is lactic acid. Determine the stereochemical configuration of lactic acid and write it underneath the structure. For the three structures 2. to its right, circle the one(s) that has (have) the same stereochemical configuration. CH3 Tom / CH; \ \ \I'C '; ’5: I 'C I “'0 HO““ \ ’ 2 HO““ \ H““ \ HQZC/ H H/ CH3 / HO/ cogH (4 Points) The following compound is ephedrine. Label each stereocenter with its R or S 3. configuration. :5 NHCH3 :‘l .0—0 rxfi Ho‘s A“ \ H) CH3 Student ID #: Name: 4. (5 Points) The specific rotation of a pure, chiral compound is +172°. Calculate the observed rotation for a solution prepared by dissolving 300 mg of the compound in 15.0 mL of solvent and placing it in an optical rotation sample holder that is 10.0 cm long. 1°) 0L Cummfiml L700 ’ t )oyom : {elm .n 3; >~ L 52: \M r O ,1 :5Cn/ C I V I I _ i O C‘ 743/14) L C [A bimk + .L 04 lfiibmk {lodeO new ‘ ca ' ’2 at : ran/v » 3‘: ‘90 5. (6 Points) Transcribe the dash—wedge structure of 2,3—dichlorobutane on the left onto the Fisher projection scaffold on the right. Cle Mffiog 50 1'7 13 TH E §/~\"’\E A S l C ‘ l l ( A7 W C \ H - ’4- M H (H y (H?) 6. (2 Points) How many stereoisomers of 2,3-dichlorobutane exist? “L , , _, Q : Kl (mt: (0055mm. {7st (WM 3 Mi 3! Student ID #: Name: Chemistry 128A — Winter Quarter 2008 MWF 12: 10 am. — 1:00 pm. Dr. Timothy E. Patten Quiz #5 (30 Points), November 7,2008 1. (4 Points) Provide the IUPAC name for the following compound. (9— 5 --(:L«mmmmmd~1v cam/r: 2. (4 Points) Calculate the index of hydrogen deficiency for camphor: CIOHIGO. Show your work. ’ \'3'M0\ ’— —\/ 1 ~-—-/-_ " g 1. Z, r’ 3. (6 Points) Arrange the following compounds in order of increasing acidity (i.e., least acidic on the left, most acidic on the right). What chemical trend accounts for this ordering? PH3 ASH3 NH3 ' I 1 \3 ' t ‘ ' ' ' A “H Si‘“- 0! ML 90"?” 0 Cl 0 O OH ‘ OH _ . CI L‘ L) u Q? \ \ r/\/\LOH 4 /')\./"\OH 4 /\‘/L \Ci} W OUQNE 5 LC CWM Lu {womum 3i Emmy (C) HCI H23 PHa only 4 Dis < no 1 _ N , x r: Lem/We N as qmvi u or (om/VAL WM“ Name: Student ID #: 4. (4 Points) List the pKas of the following compounds to the first decimal place. A) H30“ ' l‘jr B)H20 l7? 5. (8 Points) List the pKas of the following compounds rounded to the nearest whole number. '3 CH30H (5 (gal-I PM Fj)‘. was i: 60 e f ‘ CH3-NH3 U CH9 6. (4 Points) Based on your answers in questions 4 and 5, Calculate an equilibrium constant for the following reaction. Show your work. A): G CO2H oo2 \ H 09 + '——“—— H20 + : Keq = - (Hg: )6} A (pita LifT ’ (“‘1 “will Student ID #: Name: Chemistry 128A — Winter Quarter 2008 MWF 12: 10 am. — 1:00 pm. Dr. Timothy E. Patten Quiz #6 (30 Points), November 14,2008 l1] 1 4 Score: 1 ‘L \ l. (2 Points) Provide the IUPAC name for the following compound. CIA/Va EA 6L trtxfl 5 2. (6 Points) Draw the products of the following reactions. Be sure to include stereochemistry where appropriate. 12H \ H2804,H20 ../\l/\ —* l l \/ \ 1) HgSO4, H20 ( - ——’ l 2) NaBH4 \/ (mt (A \K Name: Student ID #: 3. (6 Points) Draw the products of the following reactions. Be sure to include stereochemistry where appropriate. 0 We 9’ {b- /V W /'\ \\ eh CH7 0:) EM \ Q; Fll H “ gull ./ "’ C12 \ \\ _. \ r H20 \/ 4. (6 Points) Draw the mechanism for the following reaction (Note: grading on this problem will be rather picky). OH /\/\ + Br2 + ___> + HBr /" A) Hg \ ,x/ /\D I ' ) A ‘ 8 //\/\ + 1‘3» *9)» < r “(3’ ~ 5 {IS-1%)) ' H ‘ H; l.\/\/\ r “’va «fl ‘ " Q3 l/F\ ~\\\fl / / u {fa/H ~/\\ 0 H “Ll )l O (b _' " (I ) \ r l f O , ‘5‘ \ i H 0‘ \\ q 7. \/\//\ a mi ...
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This note was uploaded on 10/22/2010 for the course CHE 128A taught by Professor Patten during the Winter '07 term at UC Davis.

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CHE128A Quiz 3-6 W07 Key Patten - Student ID Name Chemistry...

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