Exam #1 Student Name: Honor Pledge

:

CH231 Organic I

Jennings (print please) (signature)

Feb. 3, 2009

You have 80 minutes to complete this exam. Exams are due at 6:20 PM. Partial credit will be given when applicable, so remember to show your work. 1. IUPAC Nomenclature (10 pts, 2 pts each) Draw the structures of the molecules written below or provide the names of any structures shown.

Br

4-isopropyl-6-ethyldecane

2-fluoro-3-methylpentane

4-(2,2-dibromoethyl)-3,5-dichloroheptane

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2. Structure and Bonding (10 pts) The structure of urea is shown below. Please answer the following questions.
O H2N C NH2

(a) Fill in any non-bonding valence electrons that are missing from the line-bond structure. (4 pts) (b) What is the hybridization of the carbon atom? (2 pts) (c) What is the hybridization of the nitrogen atoms? (2 pts) (d) What is the predicted NH2-C=O bond angle in urea? (2 pts)

3. Valence electrons (15 pts) Please provide the following information with respect to atom valences according to the following sections. (a) Give the ground-state electron configuration for carbon. (3 pts)

(b) Give the ground-state electron configuration for fluorine. (3 pts)

(c) How many electrons does nitrogen have in its valence shell? (2 pts) Draw its ground state electron configuration. (7 pts)

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4. Drawing Structures (15 pts) Draw the corresponding structures as indicated. (a) Convert the following molecular formulas into skeletal structures that are consistent with valence rules (10 pts).

C2H7N

C3H7Br (provide 2 structures)

C2H6O (provide 2 structures)

(b) Convert the following Kekule structures into skeletal drawings. (5 pts)
H C O C C O

H C C C C H C C N H C H H H

H H

C C

C C

H H

5. Acids and Bases (15 pts. total) Please follow the directions carefully. (a) Put a box around all the Lewis acids in the group of compounds below (4 pts).

O CH3OH N BCl3 HCl FeBr3

(b) Using the curved arrow formalism, show the flow of electrons and products for this reaction. (3 pts).
H H3C O CH3 + H O H

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(c) Refer to the following equation to answer the questions below. Place the letter corresponding to the correct answer in the blank.
A OH pKa = 18 + B K+ -OH C O- K+ + D H2O

pKa = 15.7

The strongest Brønsted-Lowry acid in the equation is The strongest Brønsted-Lowry base in the equation is Will this reaction take place as written? Explain. (4 pts)

. (2 pts) . (2 pts)

6. Resonance (10 pts. total) Please provide the resonance structures below as prompted. Partial credit will be given when applicable. (a) Draw the resonance structures for the species below.
CH3

O

(b) Draw the resonance structures for the species below.

O CH2

(c) Draw the resonance structures for the species below.
O

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7. Conformations of alkanes (15 pts. total) Construct a qualitative potential-energy diagram for rotation about the C-C bond of 1,2-dibromoethane, showing all conformations. Which conformation would you expect to be more stable? Label the anti and gauche conformations.

8. Functional Groups (10 pts. total) The cholesterol lowering agents, called statins, are among the most widely prescribed drugs in the world. Shown below is the structure of Lipitor® which is the number one selling pharmaceutical in the world at ~6-7 billion dollars/year. Circle and identify the functional groups within the molecule.
F

O O N O H N

HO

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Scratch Paper Sheet

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Scoring Sheet 1. 2. 3. 4. 5. 6. 7. 8. of 10 of 10 of 15 of 15 of 15 of 15 of 10 of 10

T.

of 100

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