Organic Chemistry - Midterm 1b

Organic Chemistry - Midterm 1b - CHM 1321 Mid Term 1...

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1 CHM 1321 Mid Term 1 Answers 1) Draw the following as Lewis structures: ( 4 points ) a) [CH 3 CH 2 N(CH 3 ) 2 CH(CH 3 ) 2 ] + 2 C H C H N C C H C HH H C H H H H H H H C H H H b) N OH N C C C C CO H H H H H 2 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 2 N H 3) For the following compound: 1 2 O OH 3 4 a) What is the hybridization of both carbons, and both oxygens? ( 4 points ) C 1 = sp 3 C 2 = sp 2 O 3 = sp 3 O 4 = sp 2 b) Show the structure of the molecule using the LCAO method. ( 6 points )
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2 C s C O sp 3 sp 3 sp 3 sp 3 sp 2 sp 2 sp 2 sp 2 sp 2 sp 2 H H p p σ σ σ σ σ π s s O sp 3 sp 3 sp 3 sp 3 H σ H c) Label all the atomic orbitals used in part b. ( 6 points ) d) Label the bonds in part b ( 7 Points ) e) What is the geometry of both carbons, and both oxygens? ( 3 points ) C 1 = tetrahedral C 2 = trigonal O 3 = tetrahedral O 4 = trigonal 4) Give IUPAC names for the following: ( 6 points ) a) b) HO OH 2,5,6-trimethyloctane 4-methylcyclononan-1,3-diol 3 3 5) For each of the following pairs, circle the compound that best fits the criteria. Briefly justify your choice in each case. ( 9 points )
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3 a) b) and c) and Which has the lowest melting point?
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This note was uploaded on 01/16/2011 for the course CHM 1320 taught by Professor Ogilvie during the Fall '08 term at University of Ottawa.

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Organic Chemistry - Midterm 1b - CHM 1321 Mid Term 1...

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