Assignment _7 answer key - Chem 360 Homework assignment #7...

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Unformatted text preview: Chem 360 Homework assignment #7 (Chapter 20: amines and heterocycles, Chapter 21: carbohydrates, and Chapter 27 nucleic acids) Due Date: Wednesday, 05/05/2010 Do the following problems in Chapter 20: 4, 7-11, 13-15, 17—20, 27, 29, 30, 32, 33, 35, 38, 39, 42, 44 1. List the following compounds in the order of decreasing reactivity in electrophilic aromatic substitution reactions: ' /\ /\\ 4IL3 5 2. Give the mechanism of the following reactions: OH A OH o MeOH,H+ 0 “go OH _’ “go OMe / / OH OH 9” /° H ‘ ' t) H Flori»? 1‘ . .VyL-og M‘eUH ,. H0 A 8H1 is HHo' A M) WXN‘Q 0 I1 0 H H 0 \ {7. 0” “hag 3. Which one(s) of the following compounds are more acidic? Why? (a) 2-methylpyridine, (b) 3—methylpyridine, (c) 4-methylpyridine a MA C pawl s-bvlu'te (h13a‘flve altij an N) 4. When pyrrole is protonated, which atom should be protonated? Why? 2_ — Post-m n. (55mg ruu 9 h m wlvj Idaho ph-‘l! C Mo mml -’< 914,}, (. 0LL' UVWLJl orl Z— POSjel‘fo'n /' l I" W ’ (D : no vzxommuL Khulle (29 ‘lng 6’) +’\N H 6-5 H H H H 1,1 3 l I + I . . O w H 41’ 5. Give the structure of the followmg compounds H H (a) lactose: D—galactose linked to D-glucose in a [3—1,4’—g1ycosidic linkage Ho (0H /0H ‘ ‘7 I /Q/ ' Hakovt‘voflw ./ “I W" (b) maltose: a disaccharide with two D-glucose unit linked with 0L-1,4’-glycosidic linkage :65 H .0 n f .2»: RV 1;) H° «on (c) a oligonucleotide 5’-AUCG-3’ (in the final exam, the structures of the bases will be given) ((1) a dexoyoligonucleoti 15’-ATCG-3’ é‘jx q A: - 3 6. Solid phase oligonucleotide synthesis. (a) complete the following synthesis of an oligonucleotide by filling in the five rectangles: R1—O Basez-Pr I :0: I R —0 _ 1 O Basez Pr R1—o Baseypr O , ll l O o R / \R I II, 2 3 ' /P\ + ——--—-—--)-— R2 0 Rz—P=O Base1-Pr ——> l o O Base1-Pr HO Base1-Pr O O O | o 0 Solid Support | | Solid Support Solid Support Draw the structures of R1, R2, and R3 1?” -—> “36% =+ «PW/1,39“ ...
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Assignment _7 answer key - Chem 360 Homework assignment #7...

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