Sample FinalExam_Key - Chemistry 2521 Fall 2007; Final Exam...

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Unformatted text preview: Chemistry 2521 Fall 2007; Final Exam This exam has 8 problems on 11 pages, Make sure your copy is complete and correct. Printed Name (Last, First) k Scores: Problem 1: / 5 Problem 2: 2 0 Problem 3. Z 5 Problem 4. 3 f Problem 5. 2 0 Problem 6, 20 Problem 7. g 0 Problem 8. g E Total: Q fl 1. (15 pts) Answer the questions on mechanism of the following reaction: OTos _‘\\SH 0 + NaSH + NaOI‘os acetone CH CH3 3 a) Which of the following energy diagrams best represents the course of this reaction (circle the correct answer, 3 pts)? eno ngy to one rgy w readion reaction coordinate coordinate coordinate coordinate 1!) Circle the correct rate equation for this reaction (3 pts): Rate = k x [RTos] Rate: k x lRTos] x [acetone] Rate = k x [RTosl X [HS'] Rate = k x [acetone] X [H57] c) Circle the nucleophile in this reaction (3 pts): Cl“ acetone CH3 Na‘ Tos TosO’ @ (1) Circle the leaving group in this reaction (3 pts): Cl" acetone CI-l3 Na‘ Tos TosO‘ HS’ e) What type of mechanism this reaction has? (circle correct answer, 3 pts) SNl 3N2 El E2 Elcb radical substitution 2. (20 pts) Answer the questions on mechanisms of the following reactions: Reaction 1: Br CZHSONa (j ' CszoH "r/CH3 "’CH3 3) Circle the correct description of the mechanism for this reaction (7 pts): b) What type of mechanism this reaction has? (circle correct answer, 3 pts) SNl 5N2 El E2 Elcb radical substitution Br H Reaction 2: I C2H50H, H20 C 3 "CH3 65 °C a) Circle the correct description of the mechanism for this reaction (7 pts): b) What type of mechanism this reaction has? (circle correct answer, 3 pts) 8”] 5N2 CED E2 Elcb radical substitution 3. (25 pts) Answer the following questions on the structure of the molecules shown in the boxes below, a) (15 pts) Answer the questions about types of bonds that are present in the following molecule (3 pts each correct answer): Number of 0 bonds formed by overlap of Sp2 and sp3 orbitals: Number of 0 bonds formed by overlap of sp2 and sp orbitals: Number of 0 bonds formed by overlap of s and sp3 orbitals: Total number of 0 bonds: his is V“ Total number of n bonds: b) (5 pts) Circle the structure of the most important resonance contributor of the molecule in the box: :99 HzNfic‘NH2 (H :9: HZN’CQNH HZN’ED‘NHZ c) (5 pts) Circle the letter (A-D) indicating the most acidic hydrogen in the following molecule: H | H@$—CH:CH—CEC—H H H 3-bromocyclohexene l-bromocyclohexene 4-bromocyclohexene bromocyclohexane trans-1 ,Z—dibromocyclohexane (Z)»2-pentene l-butene 27butyne 1-bulanol 2-butanone ( Z )-2-pemene ( E )vzipentene (CH2=CH)ZCuLi (Z)-1 ,3-pentadiene (E ). I ,3-pentadiene {(E)-1,4»hexadiene (S)-2»chlorohexane (R)7270hlorohexane ? (R)-2-iodohexane (S)-2-iodohexane ( E)-2—hexene (Z)-2-hexene limethylcyclohexene 3-methylcyclohexene ether (2)71 ,4Ahexadiene OH \/\/k TosCl KI acetone pyridine lvhexene CH3 H2504 OH heat 47methylcyclohexene (Z)-2-hexene (E)-3-heptene (Z)73iheptene Cl OH (E)-1-bromo-1,3-dichloroilibutene 4,4—dichlom-3-buten-2—ol 50C]2 M H ? (Z)-l-bmm0»l,37dichloro—1-butene 4,4-dichloro-3-buten-1-ol Br pyndme (E)-] —bromo—l ,3-dichlor072~butene 4,4-dibromo-3—buten-2-ol 5. (20, 5 pts each) Circle the s‘ructure of the major product in each of the following reactions: Ph Ph P“ H H H H CH3 . H Ph Ph, H HQ H HQ OH H; _ ’ H.‘ _ ’ H." _C’ , I, y, HO/ ‘ CH3 Ph/ ‘hCH3 Ph/ phCH3 6. (20; 5 pts each) Draw the structure of the main product for each the following stereoselective reactions. Draw skeletal structures in the provided boxes; make sure to show the correct stereochemistry for the substituents (»2 pts for wrong stereochemistry). Ph/h-O’OH TosCl NaCN H‘C/\/ . . ‘ii/ pyridine acetone FA : cHZP/i “710/7 ‘1 Ph _ Li,NH3 ’0 \ fl _ \ UH 9/7 1.0504 C> 2. NZHSO3, H20 CHZOH (1 H2, Pd (cat.) CH20H 7. (30, 3 pts each box) Place in each box the molecule of a reagent that is required to perform each of the following reactions: 9 a/ 61/4,; 3 A 0 GB” 4mm - CZHSOH H20 "OH w C H3]: H20 AM; + CHZNH3 Toso- I V fill 0V QSH G J” gs“ CHZCIZ DMSO 10 8. (35, 5 pts each) For each of the following questions (a)~(g) circle the item that is the correct answer. (a) Which one of the following compounds has the highest acidity? CHSI H10 CHjOH LizSO4 (CH3)3CLi (CI-[3)3COH CHJCOZH CH4 (b) Which one of the following molecules is chiral? CHZCH3 CH3 H C CH CH \ CH}\MCH3 g> 3 kg 2 3 A W . CH3 CH3 (c) Which one of the following molecules is a meso compound? CL Cl CL, Br CH r / "’Cl Cl/ ‘H 3' Br H3C ‘H ((1) Which of the following Newman projections represents n-pentane? CH3 CH3 CH3 CH3 H3C H H H H H H H H CH3 H3C CH3 H H H CH3 CH3 H CH(CH3)2 CH3 11 (e) Which of the following species is NOT a nucleophile? Cl“ PH3 CZHSOH CHlLi HO’ Bil3 Nl-I3 (f) Which of the following compounds is the most reactive in the SNl reaction with H20? 1-iodo-2—methylhexane 1Aiodo-Z—methylcyclohexane S‘iodohexane iodocyclohexane 4—iodocyelohexene liiodoil—methylcyclohexane (g) Which of the following compounds will have a characteristic IR peak at about 1700 cm- 1 m a molecular ion M+ = 84in mass-spectrum (atomic mass ofC = 12, H = l, 0 = 16)? 0 0H 0 ll ll H C 0 C 3 \CI HSC/C\CH3 g H3C/ \OCHZCH3 ...
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Sample FinalExam_Key - Chemistry 2521 Fall 2007; Final Exam...

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