118AWin09MT2Key - 1 Nomenclature(12 points Give the IUPAC name for each of the following compounds include R/S or cis/trans stereochemistry Where

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Unformatted text preview: 1. Nomenclature: (12 points) Give the IUPAC name for each of the following compounds, include R/S or cis/trans stereochemistry Where appropriate, or draw the correct structure for the given name. OH Cl Cl Spbmmo‘q’bdmmbegun-21;: A) 1 q 5‘ 0 0r 1 s B 7 S-lommo'WrdaCh/m ‘2-h-Qpl‘fihol r 3) 1R, 28-cyclopentan-1,2-diol 0” “N bl’l A ° ( __ Cl 0 H "00H C) ZRJBR - lore“ S‘Propylo 3-OC'l1mo] 2.1: 5312 43:10” ’S'PW PY‘OCfln’g'fl D) 2.;eMl aq,,‘So?mpyl '2" CYClakfiKfinal OH “‘r 2. Vocabulary: (15 pts) Fill in the blanks with the appropriate vocabulary word. If two words are given circle the ct one. A) A alcohol in IR has @weak peak at about 30 / 2950/ 2200/ 1700 cm’l. B) An SN} reaction occurs wi scrambling inversion / maintenance of stereochemistry because of formation of a 539' l 3le (F cation. C) A hindered primary haloalkane with a good leaving group and in the presence of a weakly basic nucleophile is likely to undergo SNl and E1 E2 reaction. D) A molecule is dextrorotory rotates plane polarized light to the left / ight and generally has a R / S / stereocenters. E) True / als An sp2 hybridized carbon can be a chiral center. F) In an E2 reaction the leaving group leaves before / after at the same time a an H is removed by base. G) A signal on the “ski side of an 1H NMR is considered to be upfield and more less shielded. H) Diasteroemers are superimposable (not superimposabla and mirror images / not mirror ima es. " I) r is the name of the class of male hormones, While E hS is the name of the class of female hormones. J) A racemic mixture rotates light left / right 3. Mechanism: (10 pts) Show detailed reaction mechanisms for the following reaction. Include the structure of the expected products and appropriate stereochemistry for all steps. “Br H2O Wk} (Solvolysis only) H102 fl r» w N» M]: W“ a we“ .3 C2) 3 )3 ® @ o ,5 (3) H30 4. Reactions (16 pts) Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemz'stry, 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’. 5H hositreodnem /\/C|)js NaSH ' /\/§\ : 2 h, A) DMF 9' KCN C“ B) I 4- / 4- /§‘/ AK ' @ a) (o C) Egar LDA \GL q/k /\r/}\ D) /\/\I 5. Short Answers: A) Determine whether the following stereocenters are achiral, R or S. (8 pts) (2') 3 CH3 qu I QIZCHZOH CH(CH3)2@ ‘\Br 2 “\OH @ k‘CN kCHgCHZCHZCHe, HsCHzC CH3 CIHZC CHé H2NHZC Fk3) Hg) CHéCHs qu'tra‘ 1L 5 5 B) Circle the nucleophile in each of the following pairs that will have a faster 8N2 reaction. (6 pts) A) 'NH vs.'OH B) NH3VS_® C) H20vs@ C) Draw the fischer projections of the given molecule (4 pts) C1429”) cN CN “+0” oruc—l—CH: i3)»: )Cenlef’ (“3011 H Ho CH H ,. OH H 3 no” 0 garr— C) Circle the substrate in each of the following pairs that will have a faster 8N2 reaction. (9pts) Cl Q vs »V CI VS as; ear ’ Br vs E) Determine if the following pairs of molecules are enantiomers, diastereomers, both the same meso, or identical chiral molecules. (8 pts) CHchs CHZCHS A 12 E i ) S Mall; Zpl's 90.0% ON CN QHchs EN 3) NC.CECH3 H30H20‘9§CH3 meso | S V 2‘ NC'?‘CH3 N043 CHchs CH2CH3 CH3 Br . C) (:L 8 Ha Khan-e {S 6H Br Br B R r D) HiCH3 H 201—13 d :CtSlefC’orN r.) Br H H3 H Br 0% F) Circle all of the foilowing moiecules that are opticaily active. (8 pts) 7, pk Eacl's Br J! Perexi‘m /\'/ Cif’CI-Cd C} 0” OH . . . . . . /L<./ H30 (3N 6H CH3 0 CN OH" CH20H3 Br G) Look at the following IR spectrum of unknown A. Circle the molecule(s) that could be unknown A according to the IR. (6 pts) I 3. as. 00 s OCHe OH 00143 ...
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This note was uploaded on 01/20/2010 for the course CHE118A CHE118A taught by Professor Lievens during the Winter '09 term at UC Davis.

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118AWin09MT2Key - 1 Nomenclature(12 points Give the IUPAC name for each of the following compounds include R/S or cis/trans stereochemistry Where

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