Organic Chemistry - Midterm 1a

Organic Chemistry - Midterm 1a - 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 ) 2 CHCHCHNHCH(CH 3 ) 2 2 C C C HH H C H H C H N H C H C H C H H b) O NH 2 O C C C C CN H H H H H 2 H H 2) Draw the following as line structures: ( 4 points ) a) 3,3-diethyloctan-2-ol OH 2 b) [CH 3 CH 2 N(CH 3 ) 2 CH(CH 3 ) 2 ] + N 2 3) For the following compound: 1 2 N OH H 3 4 a) What is the hybridization of both carbons, the oxygen and of the nitrogen? ( 4 points ) C 1 = sp 3 N 2 = sp 2 C 3 = sp 2 O 4 = sp 3 b) Show the structure of the molecule using the LCAO method. ( 6 points )
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2 C s o N sp 3 sp 3 sp 3 sp 3 sp 2 sp 2 sp 2 sp 2 sp 2 sp 2 H H H p p σ σ σ σ σ π ss c sp 3 sp 3 sp 3 sp 3 σ σ H s H s σ 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, the oxygen and of the nitrogen? ( 3 points ) C 1 = Tetrahedral N 2 = Trigonal C 3 = Trigonal O 4 = Tetrahedral 4) Give IUPAC names for the following: ( 6 points ) a) b) OH 2,6-dimethylcyclooctanol 2,5,6-trimethyloctane 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 highest boiling 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 1a - CHM 1321 Mid Term 1...

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