exam2spr05ans - Exam 2 — CHM 2211 Spring 2005 Davidson...

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Unformatted text preview: Exam 2 — CHM 2211 Spring 2005 - Davidson Name: Kati UF mash—a.— I understand that this examination is governed by the University’s policies on Academic Honesty, and my signature below indicates that all work shown on these pages is my own. S i gnature 1. (4 points each, 28 points total) Draw the structures for the major organic products for the reactions shown below. If no reaction occurs, write “no reaction”. 0 a) ll 0 1)hotKMnO4,NaOH.H20 o a 2) H+ cl-Tot-l O b ) 0 o “ CH3 C- CH3 _NL.. / NH3,CH3OH / 0) CH3 CO,HCI o 3 AlCIalCuCI '5 H d) o O o 0 cu—E—CH u “0+ QE—o ——3- w a 3 AICI3 «radix/GM 0 it U + Han—n—d—NHZ —~H Cf H g) 1 S' BH 3 CH3CHZCH2—CEC-H ) '82 Oriaui’zmzwac'” 2) H202, H20 2. (3 points each, 12 points total) Nomenclature. Give the correct name or draw the correct structure for the following compounds. 21) b) benzophenone c CI 0 II 1. NH EDD/G @ ‘t Z 3 .—qu are -'-i Aux—Hal c) p-nitrobenzaldehyde d) 0 CH3 “ '* 1‘0H3 HO . 1- F . l @N0L 0: m-Jfi claw-ad‘ka 3. (12 points) Consider the pairs of molecules drawn below. Circle the molecule that has the greater value for the condition listed. O—OCHS vs_ O—CHZCHa reactivity toward electrophiiic aromatic substitution O—NHz vs, @ deactivation of the ring ‘3 E? C-H vs. C-CH3 rate of reaction with KCN 4. (12 points) When anisole is reacted with 2-methyl-1-propanol in the presence of an acid catalyst, the major product is 4-tert-butylanisole, as shown below. Give a detailed mechanism that accounts for the formation of the electrophile and the predominant formation of the para product. Show all important resonance structures. Be sure to indicate the correct flow of electrons using curved arrows. (EHS H+ ?H3 CH 0 + H3C-CH-CH OH _. CH 0 c-CH a O p 2 a 0% a w t“ 7H CIH’ GB 9’3 I 1' c“ -?%OH -——-'> orig—fir‘Cl-I-fifdz -‘" CHE-fraufi ---'3 CH3???“ H H H {limboka c.0393 'l" H- .. - H e——) are. - a Geo-Emma. Cece flees; 5. (12 points) Write a detailed mechanism for the formation of the imine shown below. Be sure to include all important intermediates and formal charges, and show the correct flow of electrons using curved arrows. & “KL/:0: N.—CI-I2c++3 + HZHCHZCHs i... we . _. #2993 H“'D’l b/ He; thwtcklg HE fh—l figmws " ‘H 1' V‘ H ---\ --—~7 LA/ \fi/ Ham/l A, “gag Du. / 2, “fir/Haul; N .u 6. (12 points) Complete the reaction scheme shown below by drawing the structures for the products of each of these reactions. 3 o @ ho! KMn04 gLOH‘ u a‘ NaOH. H20 g (then H”) LiAlH(0-t-Bu)3 O 7. (6 points each, 12 points total) Synthesis problems — Outline a detailed synthesis of the molecules shown below. If more than one pathway is possible, choose the one that generates the desired product in the greatest yield. Note: It may take more than one step to complete these transformations. ) H+,HLD 0H ht? ‘ ' (bl/7’) ‘1, o T I’M 9r jug fiifi 3‘05) 9' > o —-—-) *9 ma. >16 la b) o o 0 MH Ho H not! Ho \’ o /_\ D Waring” 0 ...
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This note was uploaded on 06/18/2008 for the course CHM 2211 taught by Professor Castalleano during the Spring '06 term at University of Florida.

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exam2spr05ans - Exam 2 — CHM 2211 Spring 2005 Davidson...

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