CHEM333H_practice Exam-3_Solution

CHEM333H_practice Exam-3_Solution - Chemistry 333 Exam 3...

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Unformatted text preview: Chemistry 333 Exam 3 Nov. 19, 2010 CHEM 333 Honors Fall 2010 Practice'Exam 3 November 19, 2010 4mm NAME: Be sure your exam has 9 pages, including this page. Read the directions carefully for each problem. Write CLEARLY; illegible answers will be considered incorrect. Do not use red ink. Shirl-“5‘31" Stop writing and hand in your exam promptly when instructed. Late exams will have points deducted. Please leave quietly if you leave early. 6. Put away all cellphones, pagers, notes, books, etc. You are only allowed a writing implement and molecular models. 7. Work the easiest problems first. Question 1 21 points Question 2 30 points Question 3 24 points Question 4 9 points Question 5 16 points Total n 100 points Bonus 10 points Score: __ 1 10 points Chemistry 333 Exam 3 Nov. 19, 2010 1. Multiple Choice — put the appropriate letter in the box 3 pts each (21 pts). a) Which of the following concepts explains Markovnikov’s rule as applied to the a; addition of HBr to propene? a. the relative stability of carbocations b. the nucleophilicity of bromide anion c. the acidity of HBr d. the Aufbau principle b) What is the correct order of stability of the following radicals (more stable > less stable)? - 1 2 3 a. 1 > 2 > 3 b. 2 > 1 > 3 c. 2 > 3 > 1 d. 3 > 2 > 1 c) Which atom in the following structure is preferentially protonated by a strong acid? iv Ck H C / ..\ HZC/u CH3 1' iii a. i b. if c. iii d. iv (1) What type of reactive intermediate is formed in the reaction of an alkene with Br; and water to give a bromohydrin? a. carbocation b. carbanion c. radical d. cyclic bromonium ion Chemistry 333 Exam 3 Nov. 19, 2010 e) Which of the following reactions of alkenes is not stereoselective? a. bromination (treatment with Br; in CHC13) b b. hydrogenation (treatment with Hz/Pt) c. acid-catalyzed hydration (treatment with aqueous H2804) d. bromohydiin formation (treatment with Brg, H20) 1) What type of reaction mechanism accounts for the reaction of an alkene with aqueous acid to give an alcohol? a. nucleophilic addition b. nucleophilic substitution c. radical addition d. elimination g) Which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration (treatment with aqueous H2804)? 1 2 3 4 00"!“ 1 2 3 4 Q. Chemistry 333 Exam 3 Nov. 19, 2010 2. Fill in each box with the appropriate starting material, reagent or product to complete the scheme. Make sure you indicate stereoehemistry where appropriate. If more than one product can be formed draw the major isomer or just one of the enantiomers. (30 pts) a) b) 1) BH3 / —-—-—-——> OH 2) H202, c) / _ HBr . 6r l >L/ —-—> HOOH M d) Chemistry 333 Exam 3 Nov. 19, 2010 0v 1) Hg(OAc)2, H20 Q/ / —m—b 2) NaBH4 OH 1) 03 SLOW ——-——D' 2) S(CH3)2 Hoof— Chemistry 333 Exam 3 Nov. 19, 2010 3. Answer each of the following questions. (24 pts) a.) With regards to the radical halogenation reaction with chlorine, write the initiation step (don’t forget to push arrows). flfl M LII-Ll 0% ~'-‘ LCI‘ b) What catalyzes or initiates the initiation? c) Write the product of the radical reaction of 1 equiv. of chlorine with cyclohexane. at 13 + C I? e—% 4— H CA (1) Write out the propagation step that produces the product in part c (don’t forget to push arrows). 6) Write out the one of the termination steps. (don’t forget to push arrows) O + a - we 0' “‘ U V u- +a' -—-9 ded Chemistry 333 Exam 3 ' Nov. 19, 2010 f) We talked that the chlorine radical reaction was exothermic. Does this mean 12.,mt > AH"? (Am #5 m, ydwwtay +W dug/Fwd Mkcjf K264" g) Draw the energy diagram of the exothermic reaction of chlorine with cyclohexane based on what you said in part f. WU ' h) What is t1 ostulate called that suggests the tr ' 10n state either looking like Chemistry 333 Exam 3 Nov. 19, 2010 4. Provide reagents and conditions for the following synthetic transformation. Be sure to include all synthetic intermediates. You will need more than one step to accomplish this. (9 pts) GA " ’r BT1- ‘3V fi/\ H? d/\ ’___> /j/\ k u A o H OH 5. Provide products and key transition states of oxymereuration and hydroboration of propene. Indicate whether to follow Markovnikov addition (16 pts) ‘ H + H @m if H3C H Hg<0Ac)2rrHF-H20 1 “9%) t 3% _.. ' \ 5* "‘ d" / \ K 0/. H I“ H H Ha Sc- “0 x 30 m > C\\4 “5 H .I :L; H39 #H BH3 : THF F) /—\"—“ ———"—" H 7""'§3, H H H"‘“BH2 HSCr ‘ Chemisz 333 Exam 3 Nov. 19, 2010 BONUS (14 pts) (3) Is there any relationship between global warming and the Alcohol Chapter 11? (4 pts) The, wwtw $395}le (2.3 «lull/db W"M 3Wfi wx2u/lwdx wwlol [4-K aulrv‘fi/re‘l L43 beDmA/(S‘W M 03) List at least two good leaving group derivatives of alcohols. (6 pts) {_ - «N 0 flows 3 0..., O "HO-“€43 “’5 ’03 0 6V 0 wofi‘sl-C? “"073” n } ...
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This note was uploaded on 02/20/2012 for the course CHEM 333 taught by Professor Lavigne during the Fall '09 term at South Carolina.

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CHEM333H_practice Exam-3_Solution - Chemistry 333 Exam 3...

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