322bs05_e3_key

322bs05_e3_key - Organic Chemistry 322 DL Spring 2005 Exam...

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Unformatted text preview: Organic Chemistry 322 DL Spring 2005 Exam 3 March 23, 2005 K5 1" Total Initial of Last Name C] T.A.’s Name (30 pts) (5 pts) (1 0 pts) (12 pts) (15 pts) (12 pts) (16 pts) _ 5L «a lo _ _ 1. Write the products of the following reactions. Assume normal aqueous WOfk-U5 (30 psi; M «fin/Mr . a. QB M.» ac 02H 2) co CH3 2 CV13 0 Cell b. O‘E\H 1) HCN,catbase ; CN ‘— f- < >—c:H2 \CHg—NHE-O—CHZQ Qtw“\C\/1;N 00?. ‘H21atm; C O O I + CH2=O + H—G> ?\ CH3 V13 0 n c!) HOCH—LCHCCH-COOH do $0 fl 0 O N 1 N a EtO-C-CHQ—CH2-CH2-CH2-C_OEt ) a0 : La 2) Neutralize Lo.) 1m7‘wm +~ 05w 2. In no more than en-e-ee-nt-enee explain why the boilingpoint of N-ethylacetamide (b.p. ' 205°C) is higher than N,N-dimethylacetamide (b.p. 166°C) despite the fact that their molecular weights are the same. (5 pts.) i ii 3. (a) The pKa of acetic acid is 4.76. Calculate the approximate concentration of H309 in a 1 molar aqueous solution of acetic acid. (b) The pKa1 of malonic acid (2.9) shows that it is a stronger acid than acetic acid. On the other hand, its pKa2 (5.7) shows that eOzC—CHz-COQH is a weaker acid than acetic acid. 193 Use structure(s)and no more thangne‘sentenceQO account for these results. (10 pts.) 7’0 flair-c; ~ \ k (‘ //<4t >quo/c 4/c 4 e‘ wtflxr‘cwv waldcié 0:“ (00‘ 0 {leaf ¢ oflw ~CODHZ/tka ClczlLCooHu; 3 '. Kt Ah momentum ( ken V; 5-0 wk {nut/[ey- MUM 0“ “ a sfilclrzq 4/ /c—~Q:\@‘(—’/,L—IOM£{ % (KMMRC ‘ “LU—"i" )4‘3 W14 [FAMz 4 f/C.-0 O 1. Write the product(s) oft ction below. The product is a poly _ / k m, @9me This is an example of a ___W , _ polymerization. ’ori‘uci‘pol, ' In such reaction, what is WtheArequlrement ,to achieve high molecular weights? (12pts.) 3‘20 9 O]C\A“W \o>\;.,wL \w (of MMMArSj CH3 O=C=N N=C=O OH \Q/ + HO/V ? i 64M /Nll*C/O/\/O}. \ '3 {How w Mr of ,oo/ymeh @ A9 9 Given Dithiane m N-LI ,n -Butyllithium, benzyl chloride Q—CHzCI / H’\H /< methyl iodide, ethyl bromide, propyi bromide and any inorganic reagents, i? prepare QCHZ-C-CHg-CHs . Be certain to write the structure of intermediate ,LDA products. (15 pts.) W0? >< 5g gray/UV ©CWCW/J‘w3 (304,, W0 63 W” Y O O u 0 II II 6. Given ethyl acetoacetate CHg-C-CHg-COQEt, diethyl malonate EtO'C'CHg‘C’OEt, 1,2-dibromoethane, 1,3-dibromopropane, 1,4-dibromobutane and ethanol, and any inorganic (If-CH3 . o O 0, ) grog): ngg o reagents you need, prepare methyl cyclopentyl ketone (12 pts.) 7. Given , NO , NO ,methyl iodide,ethyl bromide, and 0 CH3 H 0 any inorganic reagents you need prepare @D O 0 o ...
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322bs05_e3_key - Organic Chemistry 322 DL Spring 2005 Exam...

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