1. 2. !! HO H a Proton transfer b = Lewis acid/base c = Electrophilic addition 1. KOt-Bu 2. SOCI₂ d = E1 Elimination e E2 Elimination SO₂ + KCI HCI The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - g for your answers. Hot-Bu f = SN1 Nucleophilic substitution g = SN2 Nucleophilic substitution

1. 2. CH3 a 1. www 2. CH3 + Br a = Proton transfer b = Lewis acid/base c = Radical chain substitution HCI مار Na benzene, reflux CH₂ d CI d Radical chain addition e = Electrophilic addition f = E1 Elimination 4 HO-CH + NaBr Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. g = E2 Elimination h = SN1 Nucleophilic substitution i = SN2 Nucleophilic substitution

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1. 2. H₂C 1. MeO 2. -CH3 H₂O a = Proton transfer b = Lewis acid/base c = Radical chain substitution H3PO4 80° MeO CH3 H₂COM₂ CH3 d = Radical chain addition e = Electrophilic addition f = E1 Elimination H₂O Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. g = E2 Elimination h = SN1 Nucleophilic substitution i = SN2 Nucleophilic substitution

1. 2. Ph 1. Ph OH a Proton transfer b = Lewis acid/base c = Electrophilic addition 2. + Na CN NMe₂ DMF H₂SO4 Ph Ph H3C H CH3 H CN OH NM²₂ Tamoxifen anti (brest) cancer drug Ph d E1 Elimination = e = E2 Elimination Ph NMe₂ The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a- g for your answers. f = SN1 Nucleophilic substitution gSN2 Nucleophilic substitution

hydrogen by the resonance and the inductive mechanisms. a = acceptor d = donor n = no effect :0: 1. 2. 3. :0: ——CH,CH,CH,N(CH3)2 Ö: -S-CH3 -Ö: -N(CH3)2 methanesulfonyl Inductive effect Inductive effect Inductive effect Resonance effect Resonance effect Resonance effect alive to

What would be the major and minor product(s) of this reaction?