2212 spring 09 exam 4

2212 spring 09 exam 4 - 810 first NAME CHEMISTRY 2212 Exam...

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Unformatted text preview: 810# first NAME CHEMISTRY 2212 Exam 4 April 22, 2009 Be sure to read each question carefully. Partial credit will be assigned where appropriate. To receive full credit you must answer the question completely. Relax and good luckll l. (13 points) Draw structures corresponding to each of the following names. a. 2—propylpentanoic acid b. methyl phenylacetate c. cyanoacetic acid fl r\J(:# Clafi9a<1oc:*i'i d. 2-propcncnitrile //\C. N 0 e. acetic propionic anhydride f. N,N-dimethy]formamide SCORE Bonug TOTA L 2 Provide IUPAC names for the following structures. H30 H H>:$:o W'l” EUTEF'N D‘H. CHLD [1: 55 LE) ——~ Cl . i _ I OH Erbxo—z- PHEN‘JLHEXHNOH. eat: 2. (16 points) Using the curved arrow formalism, provide a detailed and stepwise mechanism for the Fischer esterification of acetic acid with ethanol using anhydrous HC] gas as a catalyst. h. i. NAME K E y last, first 8 1 O# 3. [10 points] Write a structure for the major product of each of the following reactions. C) O H 1. LDA, THF, -7BUC .- __+__+ “a I 0 1. BH3/THF 0” o H 1. DIBAL, toluene. -78 I56 2. 1430+ KMHO4 I CI H20 \ \. Ci 4. (20 points) Complete the following synthetic roadmap by writing the necessary reagents or drawing structures for the major products in the provided boxes. (1*or full credlt you must .cIearly draw the reagents and structures.) + 9 \ O\/ who THF (solvent) CUL P3 Fe. CHZCIQ (solvent) 0Q”: I 1. NaBH4. ethanol w OWN H 2. H30* of *—— i i 1. CHSMgBr, ether 0 + 2' H30 pyridine 0 EDGE UV 1. Lirflle.‘1 ether H (LN __.. N 2; benzene. BOUC 2- H30 1. NHOH, H20 2. H3o+ NH2 HCl Q/mfl'b H— . CH30H UV CDLH last, first 810# S. (l 2 points) Using 5-breme-5—methylhexanal and any other reagents. propose a brief synthesis for 2,2-dirnethyl-6-exehexaneie acid. 0 O _.____.—p H H Br H M0 6. (12 points) Using the aeetoacetie ester synthesis, make l-eyclopentyl-l ~ethanone from a non- eyclie alky] halide starting material. 0 o 0 OJK “Sing MOA 1—cyelepentyl4 -ethanene 7 . (12 points) Provide a brief synthetic sequence for each of the following. Note: Unnecessarin long sequences will not receive full credit. K E7 last, first 810# NAME Bonus (10 points) Butyrolactone, a cyclic ester containing four carbon atoms, reacts with ammonia to form 4—hydroxybutanamide. Using the curved arrow formalism, provide a detailed and stepwise mechanism for the formation of 4—hydroxybutanamide from butyrolaetone. < ;o + NH3 Ho/\/\[(NH2 H20 0 butyrolactone 4-hydroxybutanamide at; n.6,; "" H I:_\I_'+JL NH3 In a N H3 PJ iggl N H“:— + N u“ 63 O o .. '—‘ N + _ o : Arr" M Hi. ...
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2212 spring 09 exam 4 - 810 first NAME CHEMISTRY 2212 Exam...

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