Concept explainers
Interpretation:
It is to be explained why
Concept introduction:
The proton of the
The ease of this deprotonation also depends on the presence of a substituent on this carbon. An alkyl substituent reduces the acidity of this proton because the electron-donating character of an alkyl substituent reduces the electron-withdrawing effect of the carbonyl groups.
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Chapter 6 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Complete the following acid-base reactions. (a) CH3CH2CH2CH2Li + CH3COOH (b) CH3CH2CH2CH2MgBr + CH3CH2OHarrow_forwardRank the following substances in order of increasing acidity: (a) (CH3)2CHOH, HC≡CH, (CF3)2CHOH, CH3OH (b) Phenol, p-methylphenol, p-[trifluoromethyl) phenol (c) Benzyl alcohol, phenol, p-hydroxybenzonic acidarrow_forwardOne acid–base classification defines a base as a substance that acts as a proton (H+H+) acceptor, and is also known as a Bronsted–Lowry base. All bases contain a non‑bonding pair of electrons. In each of the molecules, identify the atom that behaves only like a Bronsted–Lowry base. The atom in compound A that behaves only like a Bronsted–Lowry base is the nitrogen. the oxygen on the carbonyl. the oxygen bonded to hydrogen. the hydrogen bonded to oxygen.arrow_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_forwardhydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone. CH,ČCH, H CH,CH, H Acetone Ethane pK, 20.2 pK, 51arrow_forwardThe Keq for the reaction: A + B ↔ AB is 3.793 What is the Keq for 2 + AB ↔ 2 A + 2 B Keq = ?arrow_forward
- Hydration of aldehydes and ketones can be catalyzed by acid or base. Bases catalyze hydration by: protonating the carbonyl oxygen making the carbonyl group more electrophilic employing hydroxide ion, which is a better nucleophile than water making the carbonyl group less electrophilic shifting the equilibrium position of the reaction to favor productsarrow_forward2. Consider the following equilibrium: H₂O(l) + HC₂H₂O₂(aq)=H₂O*(aq) + C₂H₂O₂(aq) Why will the addition of NaOH to a solution of acetic acid cause the concentration of the acetate ion to increase? ringarrow_forwardOH 6 From ethyl bromide and a substituted phenyl derivativearrow_forward
- Give 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_forwardIn each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions. Draw any nonbonding electrons to show how they participate in the reactions.(a) (CH3)2NH + HCl ¡ (CH3)2 NH+2 + Cl-(b) (CH3)2NH + CH3Cl ¡ (CH3)3 NH++ Cl-arrow_forwardAcetic acid, CH3COOH, is a weak organic acid, pKa 4.76. Write an equation for the equilibrium reaction of acetic acid with each base. Which equilibria lie considerably toward the left? Which lie considerably toward the right? Q.) NaHCO3arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning