chm2211exam1spring2005key

chm2211exam1spring2005key - Exam 1 — CHM 221 1 Spring...

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Unformatted text preview: Exam 1 — CHM 221 1 Spring 2005 - Davidson Name: E fl UF ID: 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. Signature 1. (4 points each, 24 points total) Draw the structures for the major organic products for the reactions shown below. Be sure to indicate proper stereochemistry (using dashes and wedges) were necessary. a) o 9.05 \ MCPBA 0’“ ( o '3) db .__ 2 We» UZHS CHaNHz [ tum" #2 ray. .\‘ N ‘ 0) “5’2 NBS O hv (1 ~— 2 '13 ) / on) ‘ ‘F M C10 g + H-c-c-c-N —-~ " ‘ CH3 CH3 e) t; CH3 0 9 0A3 “ K/ \K/ *HICCH3 “a (0’ “new; \ H ECHa u ll... 0 a“; o o f) 2. (4 points each, 16 points total) Nomenclature. Give the correct name or draw the correct structure for the following compounds. 13) 4-nitroaniline Wow -— I {Dr Moivrwrup -—l MN“ #87! W e) m-chloroac etophenone r - ‘ sLL. 30“ BO 9 Wants @ 3 °°”3 (av Ll—Imuww) CE 3. a) (6 points) Draw the two organic products for the substitution reaction shown below. CHzBr 6900*; m we. @“3 @A‘} m: (you-*2. b) (6 points) Draw a detailed mechanism below that supports the formation of your products. Be sure to use'arrows to show the proper flow of electrons, and include formal CH30H heat char es where needed. Q anti an all: an... wg A 3 “‘9 3 e—a 65"}. 3 q, H- gm Web-a H I/ cm ‘3‘" 6““ We c) (4 points) Which of the two products is the thermodmfl'c product? Why? 0—1 be“. {u hum. SPELL . I 4. (4 points each, 16 points total) For each of the molecules and ions drawn below, give the number of TI: (pi) electrons and indicate if the molecule or ion is aromatic, antiaromatic, or non-aromatic. A ‘ 'cf' ‘H H 211:2” “311—4: 11 1121' [fin—4’ i 516%“ (1M; awh‘a On Dh'c amt- . 5. Consider the Diels—Alder reaction shown below. t QN—H + Co E» endo and exo products 0 . ‘ . Aim. dA my Lub— a) (4 points) Label the compounds above as diene and dienophile. b) (6 points) Draw the endo and exo products for this reaction, and clearly indicate which is which. c) (6 points) At 25°C, the predominant product is the endo product; however, at 90°C, the exo product is preferred. Based on this statement, which product, endo or exo, is more stable for this molecule? Justify why you chose your answer. __._.—----I 6. (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. a) | hI CH WIMI'WM 1514-“ "M‘s"— km“ “fin? o —- CH30H20H2-0-(l3-(33H3 alkyl halide (EH3 e 6.01 omd- L049? + “3‘39?” L CJ-lbcl-lZLHLOH 4' @4495”? T PndJA—d" {edgier} + Na (0y Nil—H) ...
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chm2211exam1spring2005key - Exam 1 — CHM 221 1 Spring...

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