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mid-term2011 version2 - CHM 1321 Mid Term 1(February 4 2011...

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1 CHM 1321 Mid Term 1 ( February 4, 2011) Answers 1) Identify the stereochemical relationship between the following molecules (enantiomers, diastereomers, same molecule, meso compound) ( 4 Points ) a) b) c) d) Cl H CH 2 CH 3 CH 3 and relationship and (R)-2-bromobutane relationship OH OH and OH HO relationship H H 3 C OH H Br and Br OH relationship Br Cl Enantiomers Same Diastereomers Diastereomers 1 1 1 1 2) Draw the following as line structures: ( 4 points ) a) 5,6-dimethyloctan-4-ol OH 2 b) (CH 3 ) 2 CCHCH 2 CH 2 CHCH 3 NHCH 3 H N 2 3) For the following compound: 1 2 O 3 4 NH 2 a) What is the hybridization of both carbons, and both oxygens? ( 4 points ) C 1 = sp 3 C 2 = sp 2 N 3 = sp 3 O 4 = sp 2 b) What is the geometry of both carbons, the nitrogen and the oxygen? ( 4 points ) C 1 = tetrahedral C 2 = trigonal N 3 = tetrahedral O 4 = trigonal c) What molecular orbitals connect the following pairs of atoms? ( 4 points ) C 1 and C 2 = σ C 2 and O 4 = σ + π N 3 and H = σ 4) Give IUPAC names for the following: ( 6 points ) a) 2,5,6-trimethyloctane 3
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