CoursePack Exam 1 Key.pdf

1. Assign the hybridization of each of the indicated atoms in the molecules below. sp2 sp sp O...

1. Assign the hybridization of each of the indicated atoms in the molecules below. sp2 sp sp O 2 2 2 N sp3 O 2 H N C O sp2 2 sp sp2 2 2 2. Draw the resonance contributor indicated by the arrows below. NOTE: Be sure to show any hydrogen atoms attached to charged carbons. Draw all lone pairs and charges for full credit. S H S 4 H N C O H N C O 4 H 4 3. Draw the molecule given the IUPAC name. Br Br Br Br Br Br Br Br 2,2-dibromo-3,4-diethylhexane 2 /28 4. Draw the conjugate base of butanoic acid, below. NOTE: Draw all lone pairs and charges for full credit. O O H O O butanoic acid conjugate base 4 5. Circle all of the bases below that could be used to deprotonate ethanol (below) with Keq > 103. H O Base O H Base ethanol Base choices H Br N H S CH3 NH3 H 6 6. Provide the curved arrow mechanism for the following acid-base reaction. O O N H N H O O N N 4 7. Assign each chiral center as R/S. NH2 O H O no partial Br O H /26 S S R 4 4 4 8A. Draw the Newman projection for butane below, given the provided perspective. A template is shown for your aid. 8B. What is the relationship H H CH3 between the two methyl H H C CH3 groups? H 3C C anti H H H H CH3 gauche no partial eclipsed 6 2 9. Determine the relationship between each pair of molecules shown. Select only one answer per pair of molecules. constitutional isomers conformers O O H diastereomers enantiomers 4 constitutional isomers F F conformers diastereomers Br Br enantiomers 4 H H constitutional isomers H H H conformers H CH3 H CH3 diastereomers H CH3 CH3 enantiomers 4 constitutional isomers H H O O conformers diastereomers enantiomers 4 /24 10A. Draw the Newman projection of the chiral molecule below, given the provided perspective. 10B. What is Br the H relationship CH3 between the C CH3 H two halogens? Br H C anti F H F H gauche H eclipsed 6 2 11. Answer the H questions about the O cyclohexane molecule X. Draw all 1 substituents on C1, 2 C3, and C5. F molecule X (a) Draw the chair conformation of the (b) Draw the chair flip of the chair molecule using the template provided. conformation you drew in part (a). H F H 1 OH F H 2 H H H OH C1 6 C2 6 (c) Which chair C2 conformation, C1 or /22 C2, is more stable? 2