Quiz 1C KEY - Faculty.piercecollege.edu

<strong>KEY</strong><br />

Paroxetine (structure shown at the right) is an anti-depressant also known by the trade<br />

names Aropax, Paxil, Seroxat, and Sereupin. It is used to treat major depression,<br />

obsessive-compulsive disorder, panic disorder, social anxiety, and generalized anxiety<br />

disorder in adult outpatients.<br />

c<br />

O<br />

O<br />

O<br />

H<br />

N<br />

F<br />

1.(4) Using the notation (Atom orbital - Atom orbital), describe all FOUR bonds to the<br />

carbon labelled "a".<br />

Csp3–Csp2) σ<br />

(Csp3–Csp3) σ<br />

(Csp3–Csp3) σ<br />

(Csp3–Hs) σ<br />

2.(4) Name each functional group appearing at the following letters as labeled above:<br />

b______amine__________<br />

c_____ether____________<br />

3.(4) What is the molecular formula of the molecule drawn<br />

above?______C19H20FNO3___________<br />

b<br />

4. (1) How many lone pairs are in the above molecule?_____10 lone pairs_____<br />

5.(1) What is the least electronegative atom in the molecule above?_______H______<br />

6. (1) What is the geometry around the C at "a"? _____tetrahedral______<br />

7.(1) If the single-bonded oxygen on the functional group labeled “c” was replaced with<br />

a carbonyl group, what would be the resulting functional group?_____ketone______<br />

8. (1) How many pi bonds are in the above molecule?___6____<br />

a<br />

9. (1) What is the hybridization of the nitrogen labeled “b”?_____sp3____

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10. (10) Draw two additional resonance structures for molecule “A” in the boxes<br />

provided.<br />

OH OH OH<br />

A<br />

11. (1) Of the two contributors that you drew in question 10, which is more significant?<br />

Circle a letter: B or C ?<br />

12. (3) In the space below, draw the resonance hybrid of A, B, and C.<br />

δ+ δ+<br />

OH<br />

δ+<br />

B C<br />

13. (4) In the space below, draw the VSEPR diagram for tetrafluoromethane, CF4.<br />

Indicate which bonds are polar by drawing dipole arrows parallel to the bond. In the<br />

space next to the molecule, draw the direction of the net dipole (if any) or write “no net<br />

dipole”.<br />

F<br />

F<br />

F F<br />

all 4 dipoles cancel out due to symmetry - no net dipole<br />

14. (4) By substituting, adding, subtracting, or otherwise changing no more than ONE<br />

atom of tetrafluoromethane, draw a molecule with a HIGHER boiling point than<br />

tetrafluoromethane..<br />

2

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F<br />

F<br />

H F<br />

No longer symmetric - net dipole results in higher BP<br />

3