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8bFall10MT2key - l(l 8 pts Fill in the following blanks...

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Unformatted text preview: l. (l 8 pts). Fill in the following blanks with the appropriate word or phrase or circle the correct word in bold print. A) B ‘ acetals of glucOse are generally not digestable by humans. B) CQHUigé is a polysaccaride that is a structural building block of wood and grass, while 5,911)“ g is a polysaccaride that is used as energy storage for plants. C) A sugar which cyclizes to a 6-member ring is a gm “0%? a sugar which cyclizes to a S-member ring is a GJW ”035 . D) A nucleophile generally adds to carbonyls by a nucleophtl it (122! 6i A mechanism. E) In the aldol condensation an aldehyde can acts as a nucleophile / electrophile/ ’/ neither. F) A weakly basic nucleophile generally adds 1,2- @0 a conjugated enone. G) The Kilt?! i-FI'SLLN‘ synthesis is used to extend a sugar by one carbon. H) The formation of a hemiacetal is @ irreversible and can occur in the presence of acid / base / eithe / neither. 1) An oligosaccaride will have between 3 and )0 monosaccarides. J) The enol form of a compound is always / @I never more stable than the carbonyl form. K) The carbonyl of a class II carbonyl generally acts as a nucleophile lélectrophilQ while the carbon adjacent to the carbonyl generally acts as a- / electrophile. L) An L-Sugar has a®@onfiguration at the la t§l~£§l— E dating carbon. Xx.) 2. (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. Afr—”aw A) , CHO COOH H OH HNOg, heat fl OH 8) 'H OH ’ rt ‘OH cHZOH 000W CH0 1 KCN, HCI “CHO CH0 » D) H——}—OH _)_._.______.._, OH {4 \1 CH O 2) Pd, 88804, H2 0", 2 H C 3) H20 “2!,“ HwH ( CH0 fl’o’l, >6k E) O 1) NaOH crap?! 2 eq W \/\ l4 H 2) H30+, Heat flab 0H F) 1) CH3CH2MgBr ________, u ct! 2) H30+ 2, .3 fits each. 3. (l 6 pts.). Show a detailed reaction mechanism for the following reaction including resonance structures of the intermediates and the structure of the expected product. , " o CH3OH H3CgiCH3 C2) /U\ H2804 {V «H50 +1 0 H we»? to? :43): jig 23(2) 31346 “g“ a H We we H507 .. ‘i‘w’ P \t/ is W ”8079 . //\ ,7 OCfi @ + O‘Cflg 3 acre W297 wt (2-) v V i What is the name of the functional group in the product? 0‘ ((71 I 0 Would this reaction produce the same product with NaOCH3 instead of H2804? YlO (D 4. (13 pts) Show how you would carry out the following synthesis using the reagents show below. Show the reagents used for each step and the structure of the intermediate products formed in each step. Not all reagents need be used, some may be used multiple times. 0 O ———_> H300 OCH3 0r- crgouo HC/ Q) CH 36+:0Qa, CflgCfllOH' MW CD bLiAH-ly ® 2) {430+ Ho/VW/ HOW : CH30Na, CH3OH CH3CH20Na, CH3CH20H CH3OH, HCl +130+ H20 CH30H LiAIH4 CHgMgBr (CH3)2CHCH2MgBr (CH3)ZCHCHZCH2MgBr Brz, H20 HCI, H20, Heat NH3 CchHzBr (CH3)2CHCH28I’ (CH3)ZCHCHZCHZBr Pd/C, H2 HZCrO4 (aq), Heat soc:Z 5. (25 pts). Identify the following carbohydrates. OH CH0H 0 CH0 H “0 HO+H OH CH OH‘ HCHZOH 0H OCHchs 2 c ' D B OH CH OH OH . OH 0 o 2 HOHZC 0 H1910 HOH H 0” Ho OH 0 o CHQ'OH CHZOH 0 , F. OH OH CHZOH E G H ' OH ‘ CHZOH o . ' CHEOH HOHZC H H ‘ 0 H SH 910 0” Ho H OH H0 0 0 H OH Ho H H 0H CH OH HO OH H OH 2 K/ OH L CHZOH 1 .1 CHZOH HO CH3 ‘ Ho 0 HO H HOHzC o CHZOH Ho / 0 OH H OH H OH H0 H0 H H OH’ - ‘ 0H CHZOH CHQOH 0H 0H 1) Which of the above are disaccarides? A H K ii) Which of the above monosaccarides are L sugars? D 3 M N / iii) Which of the above monosaccarides are ketoses? E L? iv) Which of these are non-reducing due to glycoside bonds? 361 H v) Which of the disaccarides are a—linked? fl}; H 1 k A . vi) Which of the cyclized monosaccarides are pyranoses? C 1 Fl M vii) Which ofthe monosaccarides are tetroses? B 1 t * V . vii) Which of the above is glucose: ? , ribose 6’ , fructose '— viii) Which of the above is a deoxy sugar I , an alditol V' N l Pom'l’ our." exlm-v ' V111 mh‘ne is 4 {Al 6. (18 pts.) Provide the systematic (IUPAC) names of each of the following compounds or draw the appropriate structure. OH O (“4" ,2— p-ehhhovée A) ' M W I WINK" 1 z 3 z ‘ E - S’bromahkxvlve‘ad or )1 M B) NH brans-S'Bromo fer-en , 3 'l'Sopmpyl— 494nm hept‘ahd O H Babromo- Ll' ehwy/ benzalclekygle D) ;:brama' V' eMIbenzewcarloaUekrde Br ‘ . O E) 5,6-dibromo-N,N—dimethyI-S-oxononamidwkN 1 Br 3 -O>(o bultunoh (Judd F) /U\/U\OH ...
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