Q1: Rank the relative nucleophilicity of the following species in ethanol.CH3O¯, CH3OH, CH3COO, CH3COOH, CH3SQ2: Group these solvents into either protic solvents or aprotic solvents.Acetonitrile (CH3CN), H₂O, Acetic acid (CH3COOH), Acetone (CH3COCH3),CH3CH2OH, DMSO (CH3SOCH3), DMF (HCON(CH3)2), CH3OH

Summary:In protic solvents, larger, softer nucleophiles like CH₃S⁻ perform better due to reduced…

Answered: Q1: Rank the relative nucleophilicity…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.63P

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An important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted derivative: Base CH;CH2O OCH,CH3 CH;CH,0 OCH2CH3 H2 Diethyl malonate Base CH;CH,0 °C `OCH,CH3 CH;CH,O OCH,CH3 R Alkyl substituted diethyl malonate NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted derivative. Explain why.
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[Review Topics] [References] Br H3C CH3 H3C H3C 1. Aqueous ethanol + HO +] H. CH3 H. CH3 BH3 O-BH3 f=Sn1 Nucleophilic substitution g = Sn2 Nucleophilic substitution a = Proton transfer d = El Elimination b Lewis acid/base e = E2 Elimination c = Electrophilic addition 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 - gf answers. 2.
[Review Topics] [References] HO pyridine 1. SOCIl, + sO2 + H. Aqueous acetone H3C H20 H3C HBr 2. Br H OH optically active racemic f = SN1 Nucleophilic substitution g = SN2 Nucleophilic substitution a = Proton transfer d = E1 Elimination b = Lewis acid/base e = E2 Elimination c = Electrophilic addition 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. 1. 2.
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