Name: ___________________________

Date: _______ Score: /59

Polar Bonds and Polar Reactions Exercises 1. When liquid water freezes into ice, the water molecules form up into an orderly repeating pattern and it ceases to flow. (6 points) a. According to Model 1 and your firsthand experiences, which takes up less space: H2O in the orderly repeating pattern found in ice or H2O in the fluid arrangement of molecules found in liquid water?

b. Is your answer to the previous question consistent with the fact that ice floats in water? Explain.

2. Energy must be added to liquid water in order to make it boil (or evaporate) into gaseous water. In what ways does the energy that has been added change the system? (3 ponts)

3. For each of the following molecules (10 points)

a. Calculate the EN difference for each polar bond. (Assume CC and CH bonds are nonpolar.) b. Draw a dipole moment arrow for each polar bond. c. Add + and to atoms you expect to have a lack or excess of electron density. d. Sketch the electron cloud for the molecule so as to indicate areas of high and low electron density.

4. Carbon tetrachloride (CCl , boiling point = 77 C) is a very potent ozone depleter. An

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unscrupulous technician decides to dispose of 100 mL (approximately 1 mole) of CCl4 by boiling it off into the atmosphere. Estimate the percentage of C-Cl bonds in the original ~6 x 10 molecules of CCl4 that are broken during this boiling process. (2 points)
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5. It seems to me that a molecule without a dipole moment should be a gas at any temperature. What is wrong with this statement? (3 points)

6. A student decides to graph bp vs. molecular weight. This graph is shown below, on the left. a. What boiling point trends are highlighted by this graph? (2 points)

b. The alkyl bromide (R-Br) line seems out of place to this student. The student feels the alkane line (RCH ) should be farthest to the right. Construct an explanation for why she thinks this. (2
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points) (3 points)

c. Someone suggests that the student make a new graph with a different property plotted on the x axis. When the student does this, the graph comes out as she expected. What molecular property is plotted along the x axis of this new graph? (Shown above, right.) (2 points)

7. Propanal (bp 48 C) and propanol (bp 97 C), both found on in the table of molecules in Model 4, have very similar surface areas and dipole moments. Construct an explanation for the large difference in boiling points between the two. (3 points)

8. Rank the following molecules from lowest to highest boiling point. (4 points)
OH OH O OH

Summary of key intermolecular attractive forces: [strongest] hydrogen bond: polar molecules with [H on N, O, or X] and [lone pair on N, O, or F] [weak] dipole-dipole forces: polar molecules [weaker] dipole-induced dipole: when polar molecules or surfaces interact with nonpolar molecules [weakest] induced dipole-induced dipole: most important force for nonpolar molecules

9. For each molecule below, draw the conjugate acid or conjugate base or both if the molecule has both a conjugate acid and a conjugate base (e.g., water). (8 points)
O H H CH3 O O HO S O S CH3 Cl O O

H O

10. For each structure you drew in the answer to the previous question, classify it as a strong acid, strong base, weak acid, or weak base. (4 points)

11. Use curved arrows to show an acid-base reaction between each of the following pairs of reactants. In each case, the base is drawn on the right. Write the products of the reaction below each box. (6 points)

12. Mark each of the following statements True or False. If false, correct the statement. (6 points) a. The conjugate base of a strong acid is always a weak base.

b. The conjugate acid of a strong base is always a weak acid.

c. The stronger the acid, the weaker its conjugate base, and vice versa.