Chem_38__Exam_3_R2 - Name Chem 38 Exam 3-This exam is...

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Name:__________________________ Chem 38 Exam 3 —This exam is comprised of 13 problems on 7 pages. Please check to make sure that you have all the pages. 1. (9 points, 3pts each) Please tell which of the following pairs of S N 2 reactions will be faster and briefly tell why. CH 3 -I OH CH 3 -Cl OH CH 3 -OH CH 3 -OH H 3 C C H 3 C H Br H 3 C C H H Br CN CN H 3 C C H 3 C H CN H 3 C C H H CN H 3 C C H H Br HS H 3 C C H H SH H 3 C C H H Br HS H 3 C C H H SH CH 3 CH 2 OH H 3 C S CH 3 O a. b. c. 2. (6 points) Although a very small amount of cyclohexylacetylene is formed from the reaction of the acetylide anion with bromocyclohexane via an S N 2 displacement, the major product of the reaction is a different compound. Please draw the structure of the major product of the reaction and show the mechanism for the formation of the major product . Br C C H + C C H Minor Product Major Product ? + 1
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3. (6 points) Please write the mechanism for the following S N 1 reaction. H 3 C-H 2 C C H 3 C-H 2 C H 3 C Br + H 2 O 4. ( 6 points, 3 points each) In the following sets of organic compounds, please circle the structures in each set that are the same compounds.
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