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First Three Letters of Last Name:
TA Name:
Hour Exam #1 5.12 Spring 2005 Organic Chemistry I
Printed name_ Signature ID# Pre-requisite (circle one): 5.112 5.111 3.091

1. 2. 3. 4. 5.

Make sure your exam has 9 numbered pages plus a periodic table. Write your initials on each page. Look over the entire exam before you begin to familiarize yourself with its length. Do what you know first, then attempt the harder problems. Read the instructions carefully and budget your time. Show all of your work. Partial credit receives points!
Page 1 2 3 4 5 6 7 8 Total 9 XC
Possible Points 6 16 10 10 16 12 12 18 100 4 104
Total
1.
(1 pt) What is the pKa of a sp hybrdized carbon atom a) 25 b) 35 c) 45 d) 50

2.

(2 pts) a) Circle the letter of the molecule with the lowest barrier to rotation (or ringflip). b) Box the letter of the molelcule with the highest barrier to rotation (or ring-flip). a) ethane b) p¡¦(»ý·«)

3.

4.

5. (6 pts) a) Enter the pKa value for each acid in the boxes below. b) Indicate whether the reactants or products will be favored at equilibrium by circling the appropriate set of equilibrium arrows (a longer arrow is drawn toward the species favored at equilibrium).

6. (10 pts) a) Provide structures in the boxes to complete the following acid-base (protontransfer) reactions. b) For each set of reactants, draw in all lone pairs of electrons and show the electron movement by us



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