CHM 235Exam #2Summer 2005

Prof. Robinson

NameID#

Instructions:

  • Answer any 10 of the following 11 questions.
  • An 11th question may be answered for extra credit (also worth 10 points)

1. Name the five functional groups highlighted in the following compounds (2 pts each):

2. (a) Show the products that will be formed in the acid base reaction between CH3COOH (acetic acid) and Na+F-. (2 points)

CH3COOH + Na+F-

(b) Will products or reactants be favored at equilibrium if the pKa of CH3COOH is 4.76 and the pKA of HF is 3.45? ______(2 points)

(c) What products will be formed in the following Lewis acid/base reactions? Show all lone pairs and include all non-zero formal charge in the products (3 pts each).

  1. (a) Using Newman projections, draw the three staggered conformations of 2-methylbutane, looking down the C2-C3 bond. (5 points)

(b) Indicate how many gauche interactions there are in each conformation (3 pts)

(c) Circle the number of gauche interactions that will be highest in energy (2 pts)

Gauche

Interactions? ______

(Circle highest energy)

4. Write the correct IUPAC name for the following molecule (10 pts):

5. Write the correct IUPAC names for the following molecules (10 pts):

6. Draw condensed structures (such as CH3CH2CH3) for the following molecules:

  • 3-ethyl-2,4,5-trimethyloctane
  • cis-1,4-dibromocyclohexane
  • 2,6-dimethyl-5-(1-methylethyl)nonane

7. Name the functional group in each of the following molecules.

8. Convert the following Newman projection to:

a) the condensed structure (4 pts)

b) the stick or skeleton structure (3 pts)

c) name the molecule (3 pts)

9. a) Draw the most stable conformation of trans-1-tert-butyl-3-methylcyclohexane. (Show the chair conformation and show substituents in the axial or equatorial positions)

b) Draw the most stable conformation of cis-1-tert-butyl-3-methylcyclohexane. (Show the chair conformation and show substituents in the axial or equatorial positions)

10. Consider the following free radical halogenation reaction. Three different monochlorination organic products are formed in this reaction. Give the condensed structure for each organic product, and indicate how many different ways that product can be formed.

Organic ProductNumber of Ways Product Can Form

1)

2)

3)

11. The free radical halogenation reaction between 2-methylbutane and bromine gives several different products, but the major product is 2-bromo-2-methylbutane. Show how this product is formed by showing the initiation step, the propogation steps, and the termination steps in the formation of this product.

Initiation step:

Propagation Steps:

Termination Steps:

1