Organic Chemistry 354 Quiz - September 24, 1999

Dr. Sundin

1. For each of the following tell if the reaction is a(n): addition; elimination; rearrangement; or substitution:

a. Answer

b. Answer

c. Answer

d. Answer

2. Encircle the nucleophiles and underline the electrophiles.

Answer

3. For each functional group on the right, find an infrared band on the left which would be very helpful in identifying that functional group. Some of the functional groups may require more than one band. Each band on the left must be used at least once on the right!

A. 3400 cm-1 _______________ a. alcohol
B. 3120 cm-1 (weak) _________ b. aldehyde
C. 3000 cm-1 _______________ c. alkane
D. 2700 cm-1 (weak) ________ d. alkene
E. 1720 cm-1 (strong) ________ e. aromatic (arene)
F. 1640 cm-1 (weak) _________ f. ester
G. 1200 cm-1 _______________ g. ether
H. 800 cm-1 ________________ h. ketone Answer

4. Compound A, C5H10O, had significant peaks in the infrared spectrum at 2969, 2699, and 1727 cm-1. The carbon-13 nmr spectrum revealed three different carbon atoms. What is the structure of A. Answer

5. Give the mechanism of the following two step reaction using the curved arrow notation:

CH2=CH2 + HCl--> CH3=CH2-Cl Answer

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