Microsoft Word - substitution and elimination sample problems key

Microsoft Word - substitution and elimination sample problems key

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CH 2 CH 3 H I CH 2 CH 3 H I Key Substitution and Elimination Sample Problems 1:3 H 2 O:acetone CH 3 OH NaBr Br CH 3 OH Br CH 3 OH CH 3 ONa OSO 2 CH 3 CH 3 OH OSO 2 CH 3 KCN acetone CN H 3 C H H H 3 C H H + + hydride shift H 3 C H 3 C H 3 C OCH 3 H 3 C OCH 3 H 3 CO H 3 C major Sn 1 major E 1 secondary substrate good nuc, weak base Sn2 secondary substrate poor nuc Sn1/E1 OCH 3 secondary substrate good nuc, strong base, unhindered E2 major Sn2 minor secondary substrate good nuc, weak base Sn2 secondary substrate poor nuc Sn1/E1 CH 2 CH 3 H Br H 3 C H 3 C H OCH 3 OCH 3 + CH 3 H 3 C H + methyl shift CH 3 H 3 C CH 3 H 3 C H CH 3 H 3 C H CH 3 H 3 C H H 3 CO CH 3 H 3 C H H 3 CO CH 3 H 3 C H CH 3 H 3 C H CH 3 H 3 C H H 3 CO CH 3 H 3 C H H 3 CO major Sn1 all four stereoisomers major E1 secondary substrate poor nuc Sn1/E1 CH 2 CH 3 H OH CH 2 CH 3 H HO H 5 C 6 H CH 3 H H H 5 C 6 CH 3 H major E1
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C 6 H 5 C 6 H 5 C H 3 H C H 3 Br NaCN acetone CH 3 H C 6 H 5 H C 6 H 5 Br CH 3 CH 2 ONa CH 3 CH 2 OH C 6 H 5 C 6 H 5 C H 3 H C H 3 Br 1:3 H 2 O:acetone OH H 2 SO 4 H 2 SO 4 OH tertiary substrate poor nuc Sn1/E1 C 6 H 5 C 6 H 5 C H 3 H C H 3 OH C 6 H 5 C 6 H 5 C H 3 H O H CH 3 C 6 H 5 C 6 H 5 C H 3 H C H 2 H 5 C 6 H 3 C C 6 H 5 CH 3 H 3 C H 5 C
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Unformatted text preview: 6 C 6 H 5 CH 3 major E 1 secondary substrate good nuc, strong base, unhindered E2 major Sn2 minor CH 3 H C 6 H 5 H C 6 H 5 Br CH 3 H OCH 2 CH 3 H C 6 H 5 C 6 H 5 H 3 C H 5 C 6 H C 6 H 5 H 3 C H 3 C H + CH 3 H 3 C H + methyl shift CH 3 H 3 C CH 3 H 3 C H CH 3 H 3 C H CH 3 H 3 C H CH 3 H 3 C H major E1 H 3 C H 3 C + + major E1 hydride shift C 6 H 5 C 6 H 5 C H 3 H C H 3 CN C 6 H 5 C 6 H 5 C H 3 H NC CH 3 tertiary substrate poor nuc Sn1/E1 secondary substrate strong acid E1 secondary substrate strong acid E1...
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