CH 201 Name ______________________________

Exam #1

September 25, 2002

Page Points

1 ______ (06)

2 ______ (18)

3 ______ (16)

4 ______ (14)

5 ______ (23)

6 ______ (16)

7 ______ (07)

Total ______ (100)

1. In the molecule below describe the types of orbitals which overlap to form the bond indicated. (6 pts)

a. The atomic orbitals used to form the sigma (s) bond are an ________ and an _________.

b. The atomic orbitals used to form this bond are an ________ and an _________.

c. The atomic orbitals used to form this bond are an ________ and an _________.

2. Give the correct IUPAC name of the molecule at the left. (12 pts)

3. Provide structures for the following molecules. (6 pts)

1,3-Diethylcyclopentane bicyclo[4.2.0]octane

4-isopropyl-2-methylheptane

4. Each molecule below contains 2 functional groups. Write the functional groups present in each of the following molecules on the lines below.(6 pts)

5. Write the molecular formula for each of the following compounds on the line to the right (4 pts).

6. In each of the following structures or pairs of structures, which of the indicated bonds (1 or 2) is the shorter one. (6 pts)

7. a. Circle the most acidic proton of the two protons in bold. (2 pts)

8. a. Write a resonance structure for the following anion and circle the most important contributor. (3 pts)

b. Write a resonance structure for the following cation and circle the most important contributor. (3 pts)

8. Use the table at the end of the exam to look up the pKa values for the acids in the following equation.

a. (5 pts) Label each molecule as acid or base. Calculate the value of Keq for the reaction below.

Phenol (C6H5OH)

b. Does the reaction lie to the left or the right?________ (1 pt)

10. Provide the condensed molecular formulas and full lewis dot structures to the right for the following (include charge where appropriate): (9 Pts)

Lewis Dot Structure

Acetate _________________

Carbonic acid _________________

Methoxide ________________

14. Circle the strongest acid in the following pairs. (14 pts)

CH3CF2CH2OH or CH3CH2CF2OH

CF3COOH or CBr3COOH

CH3CH2CCl2COOH or CH3CH2CHClCOOH

HI or HF

15. Which ion is the stronger base? Explain why (use structures in your answer). (3 pts)

b. Are the following structures resonance structures? (2 pts)

15. Write an equation for the acid-base reaction when methanol (CH3OH, an acid that donates a proton) is treated with the strong base NaH (Na+ and H: -) Show electron pushing arrows. (5 pts)

Does the reaction lie to the left or the right?_________

16. Show the structure of the ion that forms when the following molecules are treated with HCl.

(In each case you are adding a proton, where does the proton go?) (6 pts)

17. Which of the following compounds is the stronger base? (Please Circle) (To answer this question consider which nitrogen is more basic?) Explain.(3 pts)

18. Match the following acid dissociation constants (Ka) with the correct acids by writing the Ka next to the right structure. (4 pts)

5.13 x 10-2 2.3 x 10-1 1.75 x 10-5 1.54 x 10-3

CH3COOH ________________

ClCH2COOH ________________

Cl2CHCOOH ________________

Cl3CCOOH ________________