261_oldexam3_ans - 1(24 points Draw a structural formula...

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1. (24 points) Draw a structural formula for the major organic product of each of the following reactions. Write 'NR' if no reaction occurs. Show or otherwise indicate product stereochemistry when relevant. CH 3 -CH-CH 2 -CH 2 -I CH 3 CH 3 -C-CH-CH 3 Cl CH 3 CH 3 OH CH 3 CH 3 N O O Br (NBS) F H CH 3 Br Na I O CH 3 Na NR O-CH 3 CH 3 CH 3 CH 3 Br CH 3 -C=C-CH 3 CH 3 CH 3 CH 3 -CH-CH 2 -CH 2 -CN CH 3 CH 3 CH 3 Br F I CH 3 H + K CN (a) + Na OCH 2 CH 3 (b) + Na Br + light (c) (d) + (substitution product(s) only) (e) + CH 3 -I (f) S N 2 reaction E2 reaction no leaving group + S N 2 with inversion S N 2 reaction
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2. (12 points) Order the reactions in each series below fastest (#1) to slowest (#3). 3. (4 points) Which of the following is NOT a step in the radical chlorination of cyclopentane? CH 3 -CH-CH-CH 3 CH 3 I CH 3 -C-CH 2 -CH 3 CH 3 I CH 2 -CH 2 -Br Br CH 2 -CH 3 CH 2 -CH 3 Br CH 3 -C-CH=CH 2 CH 3 I CH 3 O CH 3 S CH 3 OH The S N 1 reactions in H 2 O/CH 3 OH of (a) (b) The S N 2 displacement of halide ion by cyanide ion (
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261_oldexam3_ans - 1(24 points Draw a structural formula...

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