EXAM1Key(1) - Name: Exam 1 Chemistry 334 (Spring 2012)...

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Unformatted text preview: Name: Exam 1 Chemistry 334 (Spring 2012) Question 1 32 points _ Question 2 18 points _ Question 3 27 points _ Question 4 20 points _ Question 5 16 points Total 11 3 points _ Extra Credit 5 points _ Periodic Table of the Elements 4 l hydrogen I poor metals 5 7 ' 9 I '10 I Eh“;- : alkalimetals I nonmatals N11: 11 ' I alkali-earth metals in noble gases 13 14 15 $6 1? 13 I transatlun metals I rare earth metals Al Si p 8 Cl ’5‘. 20'21_22I23222527.232930 32333536 men»mfiaumna weean 37 as :- 4142 43 44 45 4s 47 48 -- 52 __ Iflfiflfiflflflfiflafififififlfifi Fl | led. H!” OH .1 R—EH f 4—1!- s OH (5) 71 ms: Ma— r—Ma 3‘3 0‘0. -. , Pry-on ‘ e 0 Fl 0 F! '3 °Yfi G Y T' 'i'“2 Y ’i/ H 3% OCH, Ch c 0H5, CH <———> *———b- --l'--——'—-—-'- H fl—IFH 4——-—--- ms 10 9 8 7 6 5 4 3 2 1 D Downtield region 699m Upfleld region or the spectrum of the spectrum Chemistry 334 Exam 1 Spring 2012 1) (32 points) Fill in the blanks. Draw all major products. (Note: some reactions may require more than one set of reagents). bbfi a BL ,CI-Is m o J p in ‘_.. AICI3 CH3 A) ON (ON B) heat H-GI (1 equiv) N —---- C) D) Chemistry 334 Exam 1 Bra (1 equivalent) Spring 2012 Chemistry 334 Exam 1 Spring 2012 2)(18 pioints) Comparing reactivity. Short answers: a) (4 points) Rank in order of reactivity with BrglFeBrs in an electrophilic aromatic substitution (EAS) reaction. (1 = fastest reaction to 4 = slowest reaction) CD 0“ WM 02.2%.. 012% (TWO “Mrs 52:25. E m D 69 t: m Points earned " int: think about the ability of the intermediate c) (6 points) Identify which of the below are examples of resonance structures and draw the arrows (single or double headed arrows) to show the movement of electons. Cross-out the ones that are NOT resonance structures. +l +l (\ gr; .c:> I) CH2 —-CH—CH2 <—> CH2 CH:CH2 CH CH 9% O 3 H (I 2 Points .. .Q/H earned :OH 4" ' 0 "’ ..__.. I .. “CACHQ Am? C] Chemistry 334 Exam 1 Spring 2012 3)(27 points total) a) (6 points) Circle the diene that reacts the fastest in the following Diels-Alder Reaction. Cross out any diene that will not react in a Diels-Alder Reaction. 0 ,— 3o 00 . t; D6 . Dlels—Alder __ . Dlene + I 0 ——" adduct Aciuuwl—vvcg _ I g Pomts O L5 A/ I ' earned wit D b) (6 points) Circle the dienophile that will undergo the fastest Diels-Alder Reaction cyclopentadiene. Cross out the dienophile that will give the slowest reaction. $10M Co 30°C . _ Q + Dienophile —I- Dlgfdfiger at? ' W lll | I E A B c G) c) (5 points) Circle the molecules that are aromatic. Cross out molecules that are antiaromatic. ®H M“, Egg Ll’ll‘e,’ 3912‘ l d) (4 points) For the compounds below, circle the one in which the indicated hydrogen is furthest upfield (lower numbers towards 0 ppm). Put a box around the compound in which the indicated h dro en is furthest downfield (higher numbers t ' . ox e) (6 points) For the com o a I ' i elow, label the different types of protons a W the pattern hat they should show (3, d, t, m) 0H3 555 Proton id. attern | ‘ ‘ * .'- mm H5) ,H. “A m (9 M or“? 3 Hg 0‘ (COWJD 44,4) El RC 8 b0 hex'fll’lbpf‘inal'llj) - 5. Chemistry 334 Exam 1 Spring 201 2 4) (20 points) Draw a complete mechanism for the following reactions. Show resonance structures for intermediates stabilized by resonance. (To get complete credit, draw ALL arrows to represent the movement of electrons.) Points earned Mechanism continued on next pg. Chemistry 334 b) Exam 1 Spring 2012 Points . H2504 earned g 0 0Q B / “u S‘\_OPH (3 ‘~ ® \ ©NY~I7 [D 6% a H, \ CB b5 m c: (9 0 . \ \. H;7\ 05"3"OH or H H Chemistry 34 Exam 1 Spring 2012 5) (16 points.) Propose syntheses for the following two transformations. Show all necessary reagents and reactants for each step. (You do not have to show the synthesis of any reagents.) U N02 A) --\ HUGE ALUB M C3 C) . - l / m OU‘VKCJ'py—r Hm \‘ 5/ 5, Points \Q (:020H3 earned —** ’ ” Cl B) 002cm 1 CIDZCI—[fi RODR II' 13 ha ' Colo“ 10 9 Downfield region of the spectrum Question 1 Question 2 Question 3 Question 4 Question 5 Total Extra Credit Exam 1 Chemistry 334 (Spring 2012) 32 points 18 points 27 points 20 points 16 points 113 points 5 points Periodic Table of the Elements I hydrogen alkali metals :1 alkali earth metals I transition metals poor metals I nonmetals E noble gases I rare earth metals Name: Upfield region oithe spectrum Chemistry 334 Exam 1 Spring 2012 1) (32 points) Fill in the blanks. Draw all major products. (Note: some reactions may require more than one set of reagents). Points earned NBS, noon V\ \A \ light C) CI2 FeCIs W9 D) 01% - I:J |:J I:JI:J Chemistry 334 Exam 1 Spring 2012 D D Bra (1 equivalent) No2 H) Draw para-nitro-aniline: NHL 1; ( N07, El Chemistry 334 Exam 1 Spring 2012 2) 18 points Comparing reactivity. Short answers: a)_ 78“ oints) For each pair, circle the reatant that will react the fastest in an EAS reaction. Points earned int: think about the . ability of the ' termediate b) (4 points) Rank in order of reactivity with Bra/FeBrs in an electrophilic aromatic substitution (EAS) reaction. (1 = fastest reaction to 4 = slowest reaction) 0 M @:$:% map Ukmgjzginsd E D c) (6 points) d) Identify which of the below are examples of resonance structures and draw the arrows (single or double headed arrows) to show the movement of electons. Cross-out the ones that are NOT resonance structures. +( H Y"\ AV‘b ' I) CH2——CH—CH2 q————-—-—-—> CH2 CH:CH2 4" +I§H CH sf 2 es- Q” 2 9 Points earned gid—n-J: Cl Chemistry 334 Exam 1 Spring 2012 e diene that reacts the fastest in the following ene that will not react in a Diels-Alder Reaction. 30°C Dials-Alder Ice—51L ED 6 ——" adduct _ OCH” 23$: A B C I E ndergo t e fastest Dials-Alder Reaction with hat will give the slowest reaction. 3 (27 points total) a.(6 points) Circle th Dials-Alder Reaction. Cross out any di b) {6 points) Circle the dienophile that will u cyclopentadiene. Cross out the dienophilet D. m 30°C Diets-Alder + lienop 1e -——" adduct /d) (4 points) For the compounds below, circle the one in. which the indicated hydrogen is furthest upfield (lower numbers towards 0 ppm). Put a box around the compound in which the indicated h droen is furthest downfield (higher numbers towards u :. 6 ~ e) (6 points) For the compound below, label the different types of protons and predict the patternggg they should show (5, d, t, m) Chemistry 334 Exam 1 Spring 2012 4) (20 points) Draw a complete mechanism for the following reactions. Show resonance structures for intermediates stabilized by resonance. (To get complete credit, draw ALL arrows to represent the movement of electrons.) ° 0 22:25.: © ©* El a) AICI3 6 Q[ .. a o D 9 3; E35 I @fl an )‘x 9mch 2L lmglaClH --C—... Jr NW wCl‘ ""-——39 / : \ (ll/Rh“ Jr lilac3 \ l 69 H C\ Mechanism continued on next pg. Chemistry 334 Spring 2012 Q ~—a (a / ’1 en ' Points earned Chemistry 334 Exam 1 Spring 2012 5) (16 points) Propose syntheses for the foilowing two transformations. Show all necessary reagents and reactants for each step. (You do not have to show the synthesis of any reagents.) o 0 Points Br¢ : : earned A) 0 o D M103“ {+2 / H136“- 0 c; C) ‘i‘ u I ~——-s 0/ A \H O 0 Points earned ...
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This note was uploaded on 02/20/2012 for the course CHEM 334 taught by Professor Wang during the Spring '09 term at South Carolina.

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EXAM1Key(1) - Name: Exam 1 Chemistry 334 (Spring 2012)...

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