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Sample_Exam_2 - (20 points total 1 Draw the structure of...

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(20 points total) 1. Draw the structure of the following compounds: a) b) 2-methyl-2-pentanol t -butyl alcohol 2 pts. 2 pts. c) 4-bromocyclohexanol 2 pts. 2 pts. d) 2-methoxy-2-methylbutane e) f) ethyl isopropyl ether 2,2-dimethyloxirane 2 pts. 2 pts. g) isobutylene 2 pts. 2 pts. h) (E)-2-bromo-3-methyl-2-pentene i) (Z)-3,4-dimethyl-3-hexene 2 pts. j) 2 pts. 3-phenyl-1-butyne
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(12 points total) 2. Which of the above carbocations is a secondary (2 o ) carbocation? a) Which one is the least stable carbocation? c) (2 pts.) (2 pts.) A B C (+) (+) CH 2 (+) Which is the most stable carbocation? b) (2 pts.) ~ ~ ~ ( A, B, C ) ~ ~ ~ 3. a) Which gives the lowest yield of substitution product when reacted with c) (2 pts.) (2 pts.) Br Which of the above halides reacts fastest by an S N 1 mechanism? b) (2 pts.) Br Br NaC CH ? X Y Z ~ ~ ~ Which of the above halides reacts fastest by an S N 2 mechanism? ( X, Y, Z ) ~ ~ ~ ( X, Y, Z ) ~ ~ ~
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(16 points total) 4. Draw structures in the boxes to complete the following reactions. Show stereochemistry in all cases: a) NaOCH 2 CH 3 2 pts.
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