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Final_3331_B - V A NOMENCLATURE 1 Give an aCCeptable name...

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Unformatted text preview: V A. NOMENCLATURE 1) Give an aCCeptable name, including correct stereochemical designations, for each of the following structures. (3 points each) m —__ a) w b) d) OH , ’00 F B. FACTS: 18 points. 3 points each "t ‘ ‘iace the foliowing compounds in order of increasing frequency of the bond stretch indicated by the Edna-OW. (‘l = lowest frequency, 37: highest frequency) ,V , H20: N \ H30 ‘fi‘ NHQ (DH [3 Cl C] 2. Label the hybridization of the atoms indicated in the molecule below. + as H20 9° “—“" CH3 fififi‘ EDD {r'l L) L lace the following compounds in order of increasing acidity. (“l : least acidic, 3 2 most acidic) GHSSH _ CH3NH2 CHsOH E] E El 4. Place thetollowing compounds in order of increasing reaction rate in an E1 process. (1 = slowest rate 3 = fastest rate) Ci OM M M Cl D 1 [3 ,. rmjflzéxw. 2 i"i'-Jt_in$L ‘ _, . , J .. 1 ’00 F [:l 5. In the box provided, draw the most stabie conformation of the the compound below, C(CHa)a a : CH3 CH3 6. Label the pair of compounds below as enantiomers, diastereomers, structural isomers or identical. CH20H I .. cHo - Br H H Br M CHO - I CH20H firming; m .i: i. C. REACTIONS 1) Complete each of the following by piacing in each box the correct starting matezialCS), reagents and reaction conditions, or product(s). 4 points each 1) HgSO4/HESO4/HZO ——-——-—-———-——-—-——-—-——-—-n—bv '9 . 2) NaBH4 H3C 0802 CH3 1) KCNICH3CN b) \e c, ‘ 2) Us ’ H " " H 3) (CH3D2S C) — H M..— 0 d) 1) 2 eq. NaNi-IQ \ 1 eq. I-IC ECH 2) mm c) 1) MCPBA 2) $130+ H f) OCHS OCH3 ' ' g) m— I ‘ NBS / hv + H W more stable less stable HCBI‘Z h) 50% NaOH/HZO -—‘—--‘--H"W——"-'—’—>” 1) gm\ E W H OH H C[ j) \A ‘_. 3 G14! 2% D. Mechanism: 10 points For the following roaction. propose a detailed. step by step mechanism to explain the formation of the pr lCt. Show all Intermediates and formal charges, and use curved arrows to Indicate electron flow. 0 H+ O W—f H2O 0H E. Synthesis: 10 points Syc‘ncsizc the following compound from a_lkanes. alkenes, alkynes, or alcohols ofthree carbons or fess, ar __ xxdlzmg or reducmg agents, and any Inorganic reagents. 9H 0 H CH3“ C—C wFH-CHS I CH3 CH3 F. Spectroscopy: 10 points Five infrared spectra are shown below. Place the letter of the compound in the box beside its spectrum. OH ‘ . _ CN ’0 ' CH3 H CH3(CH2)ECH2“NH2 CH3(CH2)4CH2'C\ CH3(CH2)SCE OH OH A B c E -un.__..u - I_I 3 E r i g ifliflfiggglfi I IINTIIIHI D ' “WMJMMWW~Q' I flaggrmlmffl f ‘- ' Willi m “’5” ilifiiék .1 “UHF .wg if m r mifi fiai‘ m I _ ._ gm: Hg m!“ 1;. li.. EEEEEE‘; .. 1!." 7 I "em * .. mfimflq 'IfiLnfif .: ‘i :fidzzsagifii " mmmn i “-- ‘ ' rialiasmaiiifimm5am:L. J g... Illllllllllll III HEEfiIHE-iih' "Illuminaqu III I r "mm: ,umsufigaul I I ith ~ m . Hawaii "Ea" I ‘ H}: diigfl a IHIIE """' .Illl ' llllll ' IIIIIIIIII “II I IIII . ' ; I - -I liai, ' D a i um '1; "a inn-I H‘— ‘ ‘ 1” i ' ‘ ._ :r ‘:‘I‘£‘ :‘ Illnmlllfltllflllflnllllllllm 43* § s s ..... m 3500 3000 2560 2000 1560 1500 1400 1200 1000 we see 460 200* KAI-4.: cu yum. ru-u m. ,A.,3‘U..“..f“fi?iwc' FREQUENCY . cu" Egg-Elia“- 1000 : $5553.43- z , = 1400 1200 J 3500 3000 2500 2000 1800 1600 Allin Chamicaf Corp.. Plastics Dim, Morristown. NJ. FREQUENCY . cm“ nuvnauv :' , .ll! “99% . .J m .rl! 1800 1400 1200 1000 2000 1500 FREQUENCY - CM" tum-m" FREQUENCY GROUP RANGE ism“) INTENSITY“ r A. Alkyl C-—H (stretching) 2853 41962 (In—s} Isopropyi, --CH[K’JI-13)2 1380— 1385 (s) ‘ ‘ and 1365—1370 (5‘) ten-Butyl, ——C(CH3)3 1385~ 1395 (m; k and ~ 1365 (5} B. Alkanyl C—-H (stretching) 3010—3095 (In) C=C (stretching) 1620—11680 (v) R—CH=CH2 ' 93541006 (8) and 905—920 (s) R2C%CH2 (out-of—planc I 880—900 (s) m's-RCH=CI-IR CqH bending“) 675—730 (a) rrmu-RCH=CHR 950—975 (3} C. Alkynyi ’ ECw—H (stretching) ~3300 (5) Car: (stretching) ' 2100—2260 (v) D. Aromatic Arm-H (stretching) I ~ 3030 (v) Aromatic substitution type {C—H out‘ofiplane headings) Monosubstimtcd 690—71 0 (Var? 5) and 730—770 (vary 5) - 0 Disubstitutcd 735—770 (s) m Disubstituted ‘ 680—725 (S) and '750—810 (vary. 5} - p Disubstiruted 800~860 {vent s) E. Alcohols, Phenols, and Carboxylié Acids O--H {stretching} Alcohols, phenols (dilute solutions) 3590-3650 (sharp, v) Alcohols, phenols (hydrogen bonded) 3200—3550 (broad. 5) Carboxylic acids (hydrogen bonded) 2500—3000 (brflai V) F. Aldehydes, Kefcones, Esters, and Carboch Acids ' C=O (stretching) 1630-4780 (8} Aldehydes ‘ 1590— 1740 (S) Katones I 1530—- 17.50 (3) Esters 1735—1750 (S) Carboxylic acids 1710—1780 (S) Amides 1630—1690 (s) G. Amines ' N—H 3300-3500 (m) H. Nitrnes ' c.=. N ' - 222fl—2260 I Cm) W " hbmiaxioms: s = strong, :1 "—3 medium w = weak, v = variable, ~ - appmxirnamly. ...
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