CHM235 Spring 06

Exam 1R

February 17, 2006 Name on last page please!

125 points + 1. (30 points) Lewis Structures and formula of organic molecules: (a) The skeleton of xanthine, a derivative of caffeine shown below. Add pi bonds and LP to make adenine the best Lewis Structure with no formal charges. Show all LP and pi bonds. All NH and OH bonds are shown. All Carbons are sp2. Don't show C-H.
H O N O N N N H

What is the Molecular formula of xanthine?

C__ H __ O

N __

(b) The structure of Methyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate is shown below. (DON"T NEED TO DRAW ANYTHING HERE)
H3C O O CH3 N

How many CH2 groups?. How many sp3 CH groups? Number of LP electrons

How many sp2 C's? How many rings are in cocaine? pi bonds

2. (15 pts) The reaction of sodium propanoate and hydronium chloride is shown below. O O + NaCl(aq) H OH2 + Na H3C OH H3C O Cl

sodium propanoate

hydronium chloride

propanoic acid

sodium chloride

(a) Identify Acid, conjugate acid, base, conjugate base. (b) HCl has a pKa = -5, while H3O+ Cl- has a pKa = -3. Which is the stronger acid? What is the effective pKa of HCl dissolved in water Explain. (c) The pKa of propanoic acid = 5 and the pKa of H3O+ = -3, pKa of HCl = -5 and the pKa of H2O = 16. Which direction will the reaction proceed? What is the value of Keq of this reaction?

3. (24 pts) Resonance and formal charge.

(a) Indicate the correct formal charges and draw a resonance structure for nitromethane
O H3C N O form A form B

formal charge of O = N = C =

hybridization of C = N = O =

Are both resonance structures of equal significance for nitromethane? Explain.

(b) Draw pi bonds for the three resonance structures that fit the molecules shown below. All formal charges and all H's are shown here for you.
O H3C C
-

O C H C CH3 H3C

O C C H

O C

O CH3 H3C C C H

O C CH3

Which structure is the least important resonance contributor?

4. (9 pts) Give structures that have

(a) a tertiary carbon (circle the tertiary C)

(b) a (2-methylpropyl) substituent

(c) What is the common name for (2-methylpropyl)?

5. (6 pts) Oxidation states. Given that H has an ionic charge of +1 and O has an ionic charge of -2,

what is the oxidation states of the C in the following structures.

O HO C OH H3C O C CH3

Carbonic Acid

carbonyl carbon in acetone

(15 pts) Explain the following data: (a) Neopentane, 2,2-dimethylpropane, has the following structure. Draw two other isomers of neopentane?
6.
H3C H3C CH3 CH3

BP
(b) Predict the order of boiling points: Highest, Middle, Lowest (b) 1-Propanol, CH3CH2CH2OH BP= 97*C Isopropyl alcohol CH3CH(OH)CH3 BP= 82*C Which is more volatile? Briefly explain?

8. (16 pts) Provide the best name for the following alkanes:
CH3 H3C H3C CH3 H3C CH3 CH3 CH3 H3C CH3

H3C

CH3

CH3 CH3

9. (12 pts) Draw the following alkanes from name.

4-(1-methylethyl)heptane

cis-1,2-dimethylcyclobutane

3,4-diethylhexane

10. (10 points) Functional Groups: Circle and identify all the functional groups below. NO ALKANES PLEASE.

Name:

Points from Page 1 Page 2 Page 3 Page 4 Total Total Points out of 45 points. out of 39 points. out of 43 points. out of 10 points. 137 points out of 125 points.