CHE128A Final Practice W07 Key Patten

CHE128A Final Practice W07 Key Patten - Name Chemistry 128A...

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Unformatted text preview: Name: Chemistry 128A — Winter Quarter 2007 MWF 11:00 am. — 11:50 am. Dr. Timothy E. Patten Final Exam: March 16, 2007 This will be a closed book and notes exam. This exam contains _13_ pages (including this one) and 22 questions. When you are told to start, check that all _13_ pages are present. If not, ask for help immediately. No adjustments will be made later. Student Identification Number: Group *CHs —CH2CH3 —C(CH3)3 AG° (kcal / mol) 1.70 1.75 2.20 Group -—Cl —Br Name: AG° (kcal / mol) 0.24 0.53 0.57 0.45 Name: 1. Draw the Lewis structures of the following compounds. It is not necessary to draw resonance structures. (8 Points) (3) N2H4 H-N—N’” .\ , 33‘ H (b) C032 ‘ C; u / ‘1” \ 2. Write the ground-state electron configuration for carbon. (4 Points) \slgls“ 2? 3. There are four resonance structures for the bicarbonate anion (HOCOZ'). Draw them and indicate which one(s) is(are) the major contributor. (9 Points) ["3 ; C} ‘x ‘ l K) ‘ ) + ‘ z k ‘\ (a K! |~ . ‘ : ’ \ ‘ l b \ l t...\/ 0 Ex \' \v 4:, I 'K. \ / \ i \\ , ‘(J- x W/ “v /0 u > K ‘ _ \ \ \ ; \’\ \\\‘\“/Y‘_// M ' 4. What are the hybridizations of each carbon atom in allene H2C=C=CH2? (4 Points) 7 m " {R —\ 5. Answer: (5. 1} 6. 7. Name: What is the IUPAC name of the following compound? (8 Points) ~ Omen-Mu LI '( l ~ m; Mvit r: WHO 00’ Draw the three Newman projections of hexane looking down the C3-C4 bond. Indicate which is the anti conformation. (6 Points) flak“? \T mot; C “fl H) “NW? 9“ (“5ch ll / i4 I) ‘4 I ‘1“ I X t! .t <:: rm ' 3.7 H, A {\1 T\ Draw the other chair confomer of the following molecule. Use table 1 to calculate the AG of equilibrium. (6 Points) Br ("*8 w “H Name: 8. Assign R or S designations to the chiral centers in the following compounds. (6 Points) Br OH A B C < ) F/K, ,H ( ) < > CI \ to < 5\ 9. How many stereoisomers exist for each of the following compounds? Draw the enantiomer of the compound shown in part A. (7 Points) , EL / ’Ai R Br QH tr" ‘ c; OH (9 (7," 10. List the pKas of the following compounds rounded to the nearest factor of five. (12 Points) CH3OH ._—.-. (3 H20 L] C GL ,7 v e l C J I? ‘ :7 CH3-NH3 NHs —‘——— HCI Name: 11. What is the IUPAC name of the following compound? (8 Points) Answer: \’ “ "ll; “\‘I L ‘ I" ' QC T "I “V t;_. 12. For the following lists of compounds, circle the most acidic compound and then draw an ‘X’ through the least acidic compound. (9 Points) yr" ‘- \‘.\ . (A) CCI3-CH2-OH (CFs-CHg-OHv CH3-%H \\M W// / “‘3 (B) < H—I“) W74 H—Br (C) CH2=CH2 CH H3 (JCECH > Name: 13. Draw the mechanism of the following reaction. Be sure to include all lone pairs and to use arrows to indicate the flow of electrons (Warning: the grading on this mechanism problem will be rather picky about such details). (12 Points) CH CH I 3.. .. I 3.. CO® ..e CH3~(I3-Br: + 2 H—O—H ——> CH3—(l3—O—H + H—CID—H + :Br: CH3 CH3 H o. .’ y m7 rs“ \ ' 2 v Ci ll *) " ‘ i. I- k “l ', f ' ' \ t, \ ix \ H7 (ll) 'H l, l 3 l {f l / Mi . I y - t ‘ P V ‘ L ’* (..’_ Q», guy L a, r ls-u—i fl Ml) \ l l 1,, i n ml 3 ~ , , 4/\\ (H- it"! b ' c; it * 7 ' a [0/ ,V \ \ "ui. M I , a u, ~ _,,H __> r, _,; ,. Hi, a r H 9. tin-k 9 ‘ i t, " \ < i \‘4 V ,‘l Viv, ( Name: 14. Draw the mechanism of the following reaction. Be sure to include all lone pairs and to use arrows to indicate the flow of electrons (Warning: the grading on this mechanism problem will be rather picky about such details). (12 Points) (and enantiomer) ’V/’/‘—\ N. \\v‘l k‘fiflk‘® __,.——S It \“t \l (5’ / x L’— / \ + r1 Pf"k ____.< \ “*‘,1’,/‘ V, I?) V (-— l ‘ ¥ ‘ If, 2 \ // v\‘ f \v l \ \ // ‘ 9 V In /' V * l” “‘ a ‘i ’ 15. 16. 17. Name: CHSBV + OH Reaction Coordinate In the following pairs, circle the better leaving group. (8 Points) (If? (A) cr or A (B) QH‘; or CH3~ <C> F or (D) NHZ' or Fwill be solvated most strongly in which solvent (circle one)? (3 Points) C H3 H3 l C H3] ‘CH3 Draw the energy diagram for the following reaction. Include the structure of the transition state. (10 Points) Name: 18. For the following starting materials and conditions, draw the reaction product(s). Remember to Show stereochemistry where appropriate. (20 points) HCI HBr, ROOR —————-———-—> 1) Hg(OAc)2, H20 \ /° ‘3’ 2)NaBH4 I \ / 1) BH3-THF '———'—'——> 2) H202, 1)Os 2) (CH3)2S 10 19. Name: For the following starting materials and conditions, fill in the boxes with the reaction product(s) or reagent(s). Remember to show stereochemistry where appropriate. (20 points) MH MH MH (5 Brz, LiBr CH3002H H9804, H2804 H20 1) (sia)zBH —--—-——-—-—--> 2) H202, NaOH Brg, hV ll Name: 20. Propose a sequence of reactions to transform the starting materials into the product. (12 Points) Starting Materials Product Br W + H —-—_ H / Nlelk (3 H ‘ I‘M \\ L Lu “W /L "‘ . x ’ ( w/ x) 7 I (M W “I”, 9 (up; ”\ «(Aim VI)» 1! \3 7 \\/\//:‘ h 9 \/\/> 2pm bur-LU v \ 21. In the following pairs, circle the better nucleophile. (8 Points) (A) OH’ or SH (B) OH' or (CH?) (C) H20 or (E) CH3C02 or @H3CH29 J) 12 Name: 22. For the following reactions, state whether the reaction would occur via an SNl or 8N2 mechanism. (8 Points) 0' OCH3 CH30H , ‘3 Answer: ‘ N 0' SCH3 < ,7 NaSCHa "N Answer: DMSO B NaCN 3‘“ Z \/\/ r WON Answer: Acetone CH3002H ‘5‘ \ WI 0 ‘D'N W \n/ Answer: 0 l3 ...
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