322bs04_e4_key

322bs04_e4_key - flmfi‘cc Organic Chemistry 322bL April...

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Unformatted text preview: flmfi‘cc Organic Chemistry 322bL April 21, 2004 4th Hour Exam Name Initial of Last Name T.A.’s Name 1.__________________________ (38 pts) 2._____________________ (15 pts) 3._____________________ (16 pts) 4.____________________ (12 pts) 5.________________ (10 pts) 5-_________________.________ (1 0 pts) Total l 1. Write the products of the following reactions. (38 pts.) .__———__—.—. re W1. 61-03%? vi; cw“:— m .=14C 6H2-CH=C 02 CDL’CM 3 cut. d. H3 Q15 NaOH/KOH A 30? Nae 0 ('3 W Br2/CH30 Na? ._.. it 9' Q—C—NHZ CH3OH ’ / W“ “Gag N02 7— NH2 —— 1) NaNO2/ HCI Q“) -.-_-, i. H 044.3 2) / weak " 0 base CH3 CH3 . NH2 1) NaNOz, HCI c '6 j. 0/ 2) CuCN g CH30 100°C ()3 1) NaN02 , HCI k. [ ——————» “I‘ H (:3 N§D Ph-CH2NH2, dilu e HCI I. <:>=O W t O'NH‘CMW 0* /H M; Man-H, m. H OH 3Ph-NHNH2 . H OH LzfiflNH-P‘h CH2OH “iron {MM n “V” 0 w “or” ' H: :3“ Ema min +. CHZOH "0 H n W) o H \C/ 0- OH OH CHZOH 2. Do either (a) or (b). if you do both only (a) will be graded. (15 pts.) H3 (a) Given toluene prepare Br Br CN we». I ‘ vista. (3 Wm” W , N400; [E j 6, m 3.34%} OH (b) Given benzene prepare Q/ ' Mull“ Given aniline, toluene, sulfuric acid, chlorosulfonic acid, acetyl chloride, acetic anhydride, and any inorganic reagents you need prepare the sulfanilamide below. (16 pts.) 0 (R o Oil “"9 Qua‘gva y wo"“c’ Nfiaclg Q... NH2 Place numbers next to the nitrogens in the biologically important heterocycle histamine: the most basic (1), the next (2), the least basic (3). In what type of orbital is. the lone pair of electrons of the least basic N. In no more that ten words explain why it is least basic. (12 pts.) I K 2- 2- 2 2. i / 3 \m 95%“ ‘5 Wk ‘5‘ 7': \‘fiqv Z Q’V‘My'Llc—v 975%. CH20H CH20 5. HO 0 H H CHZOH HO HO 0 If you dissolve the disaccharide above in water, does its specific rotation of plane polarized light change or not? Use chemical reactions or structure of functional groups to acgaount for your answer. Is it a reducing sugar? Does it react withTollens reagent Ag (NH3)2 in water? If so write the products of this reaction. (10 pts.) ...
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322bs04_e4_key - flmfi‘cc Organic Chemistry 322bL April...

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