Concept explainers
(a)
Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.
Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.
(b)
Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.
Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.
(c)
Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.
Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.
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Chapter 16 Solutions
CNCT ORG CHEM 6 2020
- Rank the following compounds in order of increasing basicity. CH3 CH3 O₂N ||| fo H3C CH3 CH3 IV A) || < | < V < III < IV B) || < V < | < ||| < IV C) IV < I< III < V < || D) || < V < ||| < | < |V H3Carrow_forwardWhen the conjugate acid of aniline, C6H5NH3+, reacts with the acetate ion, the following reaction takes place: C6H5NH3+(aq)+CH3COO(aq)C6H5NH2(aq)+CH3COOH(aq) If Kafor C6H5NH3+ is 1.35105 and Kafor CH3COOH is 1.86105 , what is K for the reaction?arrow_forwardComplete the following acid-base reactions. (a) CH3CH2CH2CH2Li + CH3COOH (b) CH3CH2CH2CH2MgBr + CH3CH2OHarrow_forward
- Write the products of the following acid-base reactions: (a) CH3OH + H2SO4 ² ? (b) CH3OH + NANH2 2 ? (c) CH3NH3+ Cl- + NaOH ?arrow_forwardIn each of the following reactions, two possible organic products can be formed. Draw both organic products in each case and then circle the one formed in greatest quantity in each case. HC (a) 1) NaH, 2) acid (b) CH,CH,OH (c) CH,CH,OH NH2 (d) Oarrow_forwardGive the products of the föllówing twó áčid-bášé réáčtións ánd for eách indicate whether reactants or products are favored at equilibrium. CHCH,ОH + CH;NH3* CH;CH,OH CH;NHNAarrow_forward
- The acid-catalyzed hydrolysis of an ester converts an ester into a carboxylic acid. Although there are two O atoms that can be protonated, the first step in the mechanism is believed to be protonation of the oxygen in the C=0 group. Based on charge stability, why is it favorable to protonate that oxygen? Hint: Draw out the products of each protonation. + Hо HO, НО Carboxylic acid Ester Alcoholarrow_forward4-Methylphenol is more acidic than ethanol (pKa 10.36 vs 16.0) , even though both contain an OH group and a methyl group. Draw the structures of the anions formed from loss of the alcoholic protons from both compounds. Use resonance to explain the difference in their respective acidities.arrow_forwardSection 1: (a) Circle the compound which undergoes decarboxylation when heated. HO2C HO,C CO,H B (b) Which carbon atom has the most acidic hydrogen in the following compound? 2arrow_forward
- (a) Rank the following molecules from most acidic to least acidic. Use the format 1>2 if you want to indicufe lis more acidic than 2. circle the molecules which can be >50% deprotonated in water nor 요.. 애 2 ii 3 A 4arrow_forwardDraw a Lewis structure of sodium ethyl mercaptide (NaSC2H5), showing all relevant lone pairs and formal charges. Based on the structure you drew, do you expect that it would act as a good nucleophile? Do you expect it to act as a strong base?arrow_forwardDetermine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products:(a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning