118BSpr11MT1Key - ]. Reactions: (24 pts). Draw the...

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Unformatted text preview: ]. Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct relative stereochemistry, if the reaction is racemic indicate this by either drawing both enantiorners or drawing one and writing racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. 0%? I OH I / H \2;~ W9 A) \/ H2804 ‘13) :1 H2, Pd/C B) Y Q) C9 5‘ Bl HCI (excess) M C) and M %—-———> H2304 (cat) D) ___’ ‘ C”? n heat C (CH3)COK, CHCI3 I t) t" “"‘ . E) M ——3—-——> @C e W (I) H _—. 2) H202, H20, bf iDi’s Eat/l4- 2. Reactions: (12 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct relative stereochemisny, if the reaction is racemic indicate this by either drawing both enantiomers or drawing one and writing racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. HBr, noon N:— A) M __________> Cl 3, W 5 + (CH3)3COH " 1 O H C) l 3 [AV/40 J/\/ W —“——*’ } + o 2) Zn, CHSCOOH ' €79 @ 3. Vocabulary: (13 pts) Fill in the blanks with the appropriate vocabulary word. If two words are given circle the correct one. A) The pKa of an alkyne H is about 2; while the pKa of an alkene H is about W this is due to greater 5 E VG . character in the orbitals. B) An E2 elimination with a hindered base will give the more ubstituted alkene which demonstrates H ogmann regioselectivity. C) When new groups are added to opposite faces of an alkene the reaction is considered to be syn D) False In 13 C NMR an alkene generally shows up around 120 ppm. B) A carbene generally has (a electrons around the central carbon. F) True liFals Additional substituents around an alkene make it less stable. G) A trans alkene i always always sometimes never a cis alkene. [F es never an E alkene, and a Z alkene is H) Addition of an alcohol to an alkene in strong acid proceeds by “ffi’firv Marth regioselectivity and syn / anti linixe ereoselectivity. 4. Mechanism: (12 pts.). Show detailed reaction mechanism for the following reaction. Include the structure of the expected products and appropriate stereochemistry for all steps. Assume all reagents are in excess. 012,0H30H % 7?? fig C l9 (5} {Ll / {:9 a CA /\ g ///<' “a [/75 <9 q z © WA E) s" % /¢LZ§C‘ L we * 0 CH5 1‘,“ H CH3 CH$OH 7 J + MC! 9 0 ® niam xC‘ ICH3 2' gagsfl 1/” Cl revE¥S\\)\4 5. Synthesis: (16 pts) Show how you would carry out the following synthesis. Include the reagents you would need for each step and the structure of the intermediate products formed in each step. You may use any inorganic reagents you need and organic reagents of five or fewer carbons. QA gr —-———-——> g 6. Coupling: (7 pts). In each case indicate which proton is described A, B, C, D or none of the above. Hc Hb Hd7€~<Ha A) The coupling between Hc and H3 is a V {CAM‘Q' type coupling with a Cl: 5 orientation. It generally has a range of {9 ~ M Hz. Couplings of this type will b sometimes / never give a doublet at Hc. it B) The coupling between HA and HD is a is a QM type coupling W generally has a range of § 2’3 Hz. Couplings of this type will be always / @ never give a doublet at HA. 7. Nomenclature: (8 pts.) Provide the systematic names or structure of each of the following compounds include E/Z or R/ S where relevant. OH g y A) 1 /€-{ ///1 E? no A}: i 5' u 3 (’5 E)~L/—ejk~1l-‘iflvclimeik1ldu-3-en-(g'\/v1-2-cl Br B) a 1 all-B-bmmo—t’a-isaa propinyCloLexer-e ‘ (L13-3’Emnnu 45 ’ {H‘ii‘rx‘ii elk?! Cycloh up: ‘Er D) (1 E,32)-2-bromo—5—butyl-8,8-dimethylcycloocta—1,3-diene 8. Spectroscopy: (20 pts.) The unknown compound A (C10H1402).gives the following proton and carbon NMR spectra Significant IR peaks were also observed. What is compound A? M 1M 2M»); " HA H3 2 6 5 4 3 - 2 1 200 150 100 50 0 IR: 3342 (broad), 3098, 2947, 2207, 1700, 1645, 1210 and fingerprint cm“. Ha=lHJ=16Hz(d),7Hz(q) 535:4 7 Hb=1HJ=16Hz(d),2Hz(q), V IrIc=3PLJ=7Hz(d),2Hz(d) ’l h x 5‘:— ! {3:414 C \ '7 CH3 /{ lpfi’ m...“ \ g f“ /# y’C‘O \ \hN/ 53C @ l 6 gap}- CH CH Pb ij W 53H x 7’ 212T ...
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This note was uploaded on 02/21/2012 for the course CHE 118B 118b taught by Professor Many during the Spring '12 term at UC Davis.

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118BSpr11MT1Key - ]. Reactions: (24 pts). Draw the...

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