02Exam2 - Name_ (Last) (First) CHEM 61 HOUR EXAM II October...

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Name___________________________________ (Last) (First) CHEM 61 HOUR EXAM II October 25, 2002 Please answer all questions succinctly in the space provided . (8) 1. Draw bond–line structures for the following substances: ( Z )–3–fluoro-3-heptene trans -2-methyl-3-hexene F (12) 2. Secondary halides can undergo nucleophilic displacement by either an S N 1 or S N 2 process, depending on the reaction conditions. Show how the stereochemistry of the product(s) from treatment of the following chloride with ethanol would vary depending on which mode of reaction occurred. Cl C 6 H 5 H CH 3 CH 3 CH 2 OH Δ S S N 1 reaction would give: OCH 2 CH 3 C 6 H 5 H CH 3 CH 3 CH 2 O C 6 H 5 H CH 3 + R S N 2 reaction would give: CH 3 CH 2 O C 6 H 5 H CH 3 Which mode of reaction would be expected in this case? Why? S N 1 CH 3 CH 2 OH is a protic solvent (and a weak nucleophile) The chloride is 2° and benzylic.
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(28) 3. Rank each of the following series according to the indicated property by writing “highest” and “lowest” under the appropriate members. nucleophilicity
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02Exam2 - Name_ (Last) (First) CHEM 61 HOUR EXAM II October...

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