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310M-makeup-KEY - CH 310/318M — Makeup FINALWilIiams —...

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Unformatted text preview: CH 310/318M — Makeup FINALWilIiams — Fall 2010, MWF 12:00 — 1:00 pm EID: Name (print): Signature: Do Section I (Scantron) in #2 PENCIL! Do Section II in blue or black PEN! Please write the first three letters of your last name in the boxes Bubble the answers into your Scantron in advance — you will NOT have time once the exam is over to do so! GOOD LUCK!! CH 310/318M - Makeup FINALWiiIiamS — Fall 2010, MWF 12:00 — 1:00 pm EID: N 00 w 00 '_ ifs-action I Raw Total T-Score CH 310/313M - Makeup FINALWilliams — Fall 2010, MWF 12:00 — 1:00 pm EID: Characteristic 1H NMR Chemical Shifts Hydrogen Type Chemical Shlft (El) Hydrogen Type Chemical Shaft (El) (CHglssi 0 (reference) RC(0)CH R 2 _ PART 1 MULTIPLE CHOICE : choose the best answer, there is only one correct choice. 3 CH 310/318M — Makeup FINALWilliams — Fall 2010, MWF 12:00 - 1:00 pm EID: {5 PTS EA: 175 PTS in this section) 1) Which atomic orbitals overlap to form the carbon-hydrogen 0' bonding molecular orbitals of ethyne, HCECH? a. C2p + H15 c. Cspz + H15 d. Csp3 + H15 2) What is the IUPAC name of the following compound? a. 1-isopropyI-4,6-dimethylcyclohexane c. 4-isopropyl-1,3-dimethylcyclohexane d. 4-isopropyI-1,5-dimethylcyclohexane 3) which of the following are epoxides? /\0/ Z 5 :0: 0 0 a. onlyr 2 and 3 c. only 2, 3 and 4 cl. 1,2, 3and4 4) What is the IUPAC name of the following compound? Won _ b. 2-methyI-1-penten—5-ol c. 5-hydroxy-Z-methyl-l—pentene CH 310/318M — Makeup FINALWilIiams — Fall 2010, MWF 12:00 — 1:00 pm EID: d. 4-methyI-5-penten-1-ol 5] Which of the following statements is true? a. All mirror images are enantiomers b. All molecules that have stereocenter centers are chiral d. Superposable structural isomers are enantiomers 6) Which of the following is present in the highest concentration upon dissolution of HF in water? 7) The reaction of 1-bromopropane with sodium iodide gives 1—iodopropane. What is the effect of doubling the concentration of Na] on the rate of the reaction? a. the rate increases by a factor of 4 c. the rate by decreases a factor of 2 d. the rate remains the same 8) What is the major organic product obtained from the following reaction? Br OEt 1. Nail” \IA 2. EtBr 1 2 3 4 51.1 b. 2 c. 3 9) What type of molecular orbital is formed by the overlap of atomic orbitals shown? CC) C)- 5 CH 310/318M — Makeup FlNALWiIIiams — Fall 2010, MWF 12:00 - 1:00 pm EID: b. o antibonding c. Tl: bonding d. It antibonding 10) Which of the following is the strongest acid? a. CH3CH3 b. CHSNHz d. CH3F 11) Which of the following alkvl halides undergoes the fastest solvolvsis reaction with methanol, CH30H? a. methyl chloride b. ethyl chloride c. 2-chloropropane 12) Which of the following statements is not true? a. homolvtic cleavage of a bond in a neutral molecule gives two radicals b. radicals have one or more unpaired electrons c. movement of single electrons is depicted using a ”fishhook arrow" 13) What is the IUPAC name of the following compound? a. (R)—4—methy|—2-hexyne c. (R)—3-rnethyl-4-hexyne CH 310/318M — Makeup FINALWiIIiamS - Fall 2010, MWF 12:00 —- 1:00 pm EID: d. (S)-3—methy|~4—hexyne 14) Which of the following structures represent the same stereoisomer? CH3 CHlCHalz OH “H J?” u HCleclz 0H Hsc 0H Hume): $1.3 1 2 3 a. only 1 and 2 b. only 1 and 3 d. 1,28nd3 15.) What is the major organic product obtained from the following reaction? 1. (sia)zBH HacHZC-CEC-H —r-— 2. H202, NaOH b. cis-Z-butene c. 2-butanol d. butanone 16) What is the major organic product obtained from the following reaction? OH PBr Br PBr; —-3b- / 1 2 3 b.2 (L4 17) Which of the following is an accurate statement of Hammond’s postulate? CH 310/318M - Makeup FlNALWilliams - Fall 2010, MWF 12:00 - 1:00 pm ElD: b. the transition state of an exothermic reaction will resemble the products more than the starting materials (reactants) c. the transition state of an endothermic reaction will resemble the starting materials (reactants) more than the product d. the difference in energy between the starting materials (reactants) and transition state controls the rate of a reaction 18) Which of the following alcohols undergoes the most rapid dehydration upon treatment with H2504 to give an alkene? OH OH 0H \/\0H W © 1 2 3 4 a. 1 b. 2 d. 4 19) Which feature in the 1H NMR spectrum provides information about the relative number of each type of proton in a compound? a. number of signals c. splitting d. chemical shift 20) Which of the following terms describes the role of ethyne in the acid-base reaction shown? HCECé-HA Gill—:2 CH 310/318M — Makeup FINALWiIliamS — Fall 2010, MWF 12:00 — 1:00 pm EID: b. Bronsted-Lowry base c. Lewis acid d. Lewis base 21) Which of the following statements is not true regarding resonance structures? a. All resonance structures must have the same number of electrons b. The resonance structures may have different energies c. All resonance structures must have the same arrangement of atoms 22) Which of the following is not a terpene? @CQQQEC’ c. 3 d. 4 23) What is the best choice of reagentis) to perform the following transformation? m ? ..——’.. O a. 03 c. 0504; followed by NaHSO; d. H20, H250“ 24) What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with HCI to give tert-butyl chloride? CH 310/318M — Makeup FlNALWilliams — Fall 2010, MWF 12:00— 1:00 pm ED: 3. ten-bowl radical b. tert-butyl anion cl. tert—butoxide 25) What is the major organic product obtained from the following sequence of reactions? OH OH W Yk/ Hz 1 2 >6 1.HC=CNa Llndlar —)- —:-- 2 HzO OH 0 / M /|>\/ 3 4 a. 1 b. 2 I d. 4 26) Which of the following alkenes undergoes allyiic bromination to form a single monobrominated product? 0%WW 3 4 b.2 c.3 d.4 27) What is the major organic product obtained from the following reaction? NaOCH3 °°H3 \J\ \/T'\ CHgOH OCH; 1 10 CH 310/318M — Makeup FINALWilIiams - Fall 2010, MWF 12:00— 1:00 pm EID: a.1 b.2 c.3 28) How many stereogenic centers are there in the following molecule (the naturally occurring stereoisomer is the male hormone testosterone)? a. Three b. Four d. Seven 29) 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 30) What is the hybridization of carbon atoms labeled i — iii in the following structure? if H26: c=cn2 i iii a. i= sp; ii= sp; iii: Sp b. i: spz; if = p; iii = sir)2 d. i= 3:32:13": 3.02; iii = sp2 11 ZI asummd aldonowoq ;0 Had JO]. am: 5! Bumouo; 314: ,to 143ng (ME euexauopflo 'p HOOO’(ZHO)OZOH ‘pgoe ogogpauexau 'o H09(zHO}OH ‘Iomauexeu-Q‘L '9 HO 4—- ’OIH H0 auonoeaJ Bugmouo; am tum; peugemo lanpmd oguefuo Jolew an; 5! 12mm (55 v 'p 9 ‘9 I |, '8 v e a L H 1'H H "‘H H /ozH H O: 936 @133 O = (B MOHOOZH] ;o ammms sq; o1 uonnqmuoo 193619| aux saxew sampnns aoueuoseJ Sugmouo; aq; p qogqm (25 v 'P E '3 2 ‘q r e a L H H H cHo 9H0 o‘H EHo H tHo H H H H EH0 t‘14:) H “H3 H “H0 H 5H9 H 8H3 8H3 aauemqlhmaw-z p uogewaowoa a|qezs 150w aq; szuaseuda; sunmaload uewmaN Sugmouo; am ;0 '43ng (1:5 3C||3 “M 00:11 - 00131" dMW 'O'EOZ lled — SWEHHM'IVNH dnanew — WSIE/OIE H3 CH 310/318M — Makeup FlNALWilIiams — Fa|12010, MW? 12:00 — 1:00 pm EID: 1. They will appear at the same chemical shift in an achiral {i.e., nonchiral) environment 2. They will appear at the same chemical shifts in a chiral environment a. onlyl b. onlyz c. neither 1 nor 2 35) What type of intermediate is formed in the Hg2+ catalyzed hydration of an alkyne? a. an alkoxide b. an enolate d. a 1,2-diene END OF SECTION 1!! 13 CH 310/318M — Makeup FlNALWiiIiams — Fall 2010, MWF 12:00— 1:00 pm EID: Section II - Short Answer Format (225 P13 in this section) 1.) Mechanism: Hydroboration of Alkynes. Use the arrow pushing formalism to unambiguously indicate the electron flow. Draw all intermediates and push arrows for each step, being sure to include all lone pairs and charges! You do not need to draw the structures of the sia groups, simply indicating them as "sia" will suffice. Then provide answers to the following questions regarding this reaction below. (38 pts page total) (2 ea set arrows. 4 ea structure/step) H 1)(SialzBH W0 + 90” 2.)H202,NaOi-l H ’sia H20 H-‘B \. sue i 62.30.; e“UH “(2- H H ,QH H / ,5Ia / 2,189." / C)_ B —)- E).- .‘ B-‘saa | I Sla :5 r H sia H sua .. Hsra Circle the correct option in parentheses and fill in the blanks below. (12 points) One key step of this reaction mechanism involves a TAUTCIMERIZATION from an ( ENOL , ALDEHYDE ) to an ( ENOL , ENOLATE- These ( ONSTlTUTIONAL lSOMERS STEREOISOMERS) exist in equilibrium and differ by the placement of a HYDROGEMPROTON) and a DOUBLE_BDND relative to a heteroatom. 14 CH 310/318M — Makeup FINALWiIIiams — Fall 2010, MWF 12:00 — 1:00 pm EID: 2.} Resonance Structures: Book 1.75. As you learned in chapter 6, ozone is used to cleave alkenes to produce aldehydes and ketones. Draw a suitable Lewis structure for ozone, 03 below (remember that ozone is acyclicl). Draw the four contributing resonance structures of ozone, including all lone pairs and formal charges. Use the arrow pushing formalism to show how the resonance structures are converted into one another. Draw a square around the two most contributing structures. (26 pts total) Why are the other two resonance structures only minor contributors? the oxygens hearing the formal positive charge are lacking a full octet/valence Extra Credit (5 raw points): This semester we learned about asymmetric hydrogenation of alkenes, work for which Noyori and Knowles won the 2001 Nobel Prize in Chemistry. in these asymmetric hydrogenations, a chiral element (or ligand) is used to bind to the metal and create a chiral environment for thereaction. What is the name (acronymlcommon name) of the chiral ligand used in the ruthenium-catalyzed asymmetric hydrogenations we discussed in class ? 15 CH 310/318M — Makeup FINALWiIIiams — Fall 2010, MWF 12:00 — 1:00 pm BID: 3.) Chairs: Book 2.50. There are four cis,trans isomers of 2-isopropyI-S-methylcyclohexanol. Using the planar cyclohexane rings below, draw the structural formulae for the four cis,trans isomers. Then unambiguously draw THE MOST STABLE chair conformation for each of your answers using the chair templates provided. 0f the four, the most stable isomers are that found in nature: menthol. indicate menthol by circling both enantiomers. (Hint: -AG (Ax-Eq) = OH: 0.93, CH3: 1.74, lPr: 2.15 kcal/mol, keep the smallest group axial!) {28 pts.) (4 ea. Structure, 2 ea. Circle) a. lsomerl Me Chair —" 0H Me Me All eq h. Isomer ll OH Meg“ 0H Chair ME —>— Me Me Me Me ax CH C. lsomer III Me —’.. Me all eq d. Isomer IV Me “\OH Me Chair _—,.. "'ngr M8 M 0H Me Me OH ax 16 CH 310/3181“ — Makeup FINALWiIIiamS — Fall 2010, MWF 12:00-— 1:00 pm EID: 4.) Ranking. Rank the following sets of compounds based on the stated criteria for each. (38 pts} 2 pt ea 3. Nucleophile strength (I: strongest, 5 = weakest) II CH30H NaCN " NaSCHa 36/ CON\ ”0/ \OH I [BE] E] I 1:). (ZIP priority. {1 = highest, 5 = lowest} H XCHS Kcazcoon k0=cuz j‘qcnzcmcnz REHZCHZCI [BI E] E] c. Acid strength. (1: strongest, 5 = weakest) o q\\/,OH i Me/—\Me 0K0 Et\NH2 HCI E] [Z] [3 [3 d. Reactivity in solvolysis reactions with ethanoi. (1: most, 4 = least) Me Br Me |\/\ > \ M MB 17 CH 310/318M - Makeup FfNALWiIIiamS — Fall 2010, MWF 12:00 - 1:00 pm EID: 5.) NMR. For the following constitutional isomers of CsHmo below, write how many sets of equivalent protons exist on the top line under each structure. Using the bottom line space, predict what splitting pattern (singlet, doublet, etc.) might be observed in the 1H NMR spectrum for the protonls) indicated by an arrow in each structure. (36 points total) JILL .hl 0 Me \ Me 3 # H's: _..__ 4% Me # H's: —Q" l°” _(.0_ # H's: u}, # H's: 18 CH 310/318M — Makeup FINALWiIIiams - Fall 203.0, MWF 12:00 - 1:00 pm EID: 6.) NMR Spectra. The following three spectra are of three of the structures in #5. Assign the correct compound to each spectrum in the boxes provided, label the resonances in each spectra according to the "a,b,c” naming system and assign all signals to the corresponding protons in your proposed structure. (26 points) NMR Spectra A: NMR Spectra B: PPM NMR Spectra C: PPM 19 CH 310/318M -— Makeup FlNALWiIIiams — Fall 2010, MWF 12:00 — 1:00 pm EID: 7.) Fill in the Box. For the boxes A and B given below, provide the correct product. For the boxes C — L in the table below, provide the correct reagents needed to complete the desired transformation table (more than one step may be required). Make sure you put your answers in the right box! (28 pts) F racgmic \ M Me 0H 9 E Eto\/‘Q.J\// C Me racemic ‘——-—"' EtO ¢ G Me OH 2 Me, 0” Cl\/J‘<’OH / Et°\/'km\ Me racemic A M OH :5: racemic» 9, EtO ’ \D L a. .\ l“ “W0 racemic H O H OH kc, + A racemic Me 0 H \Miil's CH 310/318M — Makeup FINALWiIIiams —- Fall 2010, MWF 12:00 — 1:00 pm EID: 8.) Two Step. Fill in the boxes below with the correct products and/or reagents for the given transformations. if there is more than one step, make sure to include the reagents for both steps! if you must draw a product that is racemic, indicate so by writing “racemic”, but you only need to draw one enantiomer. (24 pts total) A. Me Me (22?; b ' H2304 I T O” —'5 ‘ + ”2° Me Me 2 2 0H (”F W \|'_(‘ END OF SECTION 2 and Exam!!! 21 ...
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