CHM 2211 TEST #1 (Fall 2013) MAKE SURE TO PLACE ALL ANSWERS ON YOUR ANSWER SHEET!!!

! WATCH YOUR TIME! 1. (27 pts) Consider the pairs of molecules drawn below for each case (a-i) and place the number that corresponds to the molecule that best satisfies the question on your answer sheet. JUST THE NUMBER!

2. (40 pts) Give all significant major organic product(s), starting materials or conditions necessary for the reactions shown below. Make sure to indicate stereochemistry where necessary. Enantiomers are not necessary. If more than one step is required be sure to indicate so with sequential steps but always follow the step restrictions or use the minimal number of steps. a)

b)

c)

d)

e)

f)

g)

h)

3. (11 pts) Give the major organic product or conditions necessary to complete the ROAD MAP BELOW. If multiple steps are necessary make sure to clearly indicate with numbered steps. No reaction should be more than 3 steps. Minimum is best!

4. (10pts) Provide a detailed mechanism to describe the reaction below. Be sure to show all important intermediates, formal charges and the correct flow of electrons using curved arrows.

5. (12 pts) NMR Spectroscopy: a) Choose which molecule corresponds to each spectrum provided. Enter the letter only on your answer sheet. b) Which molecule A-H would have the most deshielded signal? c) Which molecule A-H would have the least number of signals?