Concept explainers
Interpretation:
The leaving group in Table 9-4 that is the weakest base is to be identified from the
Concept introduction:
A weak base is stable and is, therefore, a good leaving group. The
The rate of an
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Organic Chemistry: Principles and Mechanisms (Second Edition)
- the dissociation constant of 0.25 M propanoic acid C2H5COOH is 1.3 × 10-⁵. a) What is the dissociation rate of C2H5COOH in this solution?arrow_forwardStep 1: Fast, reversible HA = H+ + A- Step 2: Fast, reversible X + H+ = HX+ Step 3: Slow HX+ = products What effect would adding A- to the solution have on the reaction rate?arrow_forwardThe 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_forward
- All of the following acid-base reactions are reactions that we will study in greater detail in the chapters to follow. Propose the mechanism and then clearly label the acid, base, conjugate acid, and conjugate base: Add curved arrows to show the mechanism for the given reaction. H 8.--8-2 OH Harrow_forwardFor the Reaction: NH3+ H2O = NH4+ OH- When adding NH3+ phenolphthalien+ HCl What stress is applied and what direction does the equilibrium shift? When adding NH3+ phenolphthalien+ NH4Cl What stress is applied and what direction does the equilibrium shift? When adding NH3+ phenolphthalien+ NaOH What stress is applied and what direction does the equilibrium shift? When adding NH3+ phenolphthalien+ HCl What stress is applied and what direction does the equilibrium shift?arrow_forwardDraw 3 RC for each of these anions (when converted to their conjugate base). Based on these, rank the order of acidity. i o 0 NE OH OH OHarrow_forward
- 6. Clearly label the Lewis acid and Lewis base in each reaction. Fill in all lone pair electrons on the reactants and products, and use curved arrows to show the mechanism of the reaction. Identify formal charges on the product(s), if not already noted. 4.x-x H st H-A-H H CH, CI fo -H AIH₂ MgBrarrow_forward1. Rank the following molecules in terms of increasing acidity. Explain your rankings in terms of stability of the corresponding conjugate base. OH HO, SH NaNH2 =H HO,arrow_forward11) For the following reaction, identify the Lewis acid and the Lewis base and draw the curved arrow mechanism. H H -N - +) NH2 lewis base lewis Aciol SHN pinb!7 (P 12) Which of the following solvents can be used with NaNH2 and why? 02H (2 (9 HOʻHO H A.arrow_forward
- aund= ney, churge Na O NH2 attack Tonic c) CH3CH2CH2CH,Li + NH3 (acid CH 3 CH2 CH2-CHz t WH2 (Conj acud) (base) (ca bu 2. The equilibrium idea means that if the reaction is reversible there will be four species in solution at one time, the acid, the base, the conjugate acid, and the conjugate base. Sometimes this is what is required, but at other times we need to choose bases that will completely deprotonate every molecule of acid, i.e. send the reaction completely to the right. These bases will include CH3CH,CH2CH;Li, NaNH2, and LiN(i-Pr)2. Weaker bases will include NaOH, NAOCH3, KOtBu, and NaOCH2CH3. For each of these bases, give the products formed when they react with H2O, then use pKa values to get an idea of the relative base strengths of these compounds. You will provided 7 separate reactions. 3. In CHEM 3112, we will study reactions based on the deprotonation of ketones such as acetone, (CH3)2C=0, which has a pKa of 19. Given the bases LiN(i-Pr)2 and NaOCH3, decide which one…arrow_forwardAll of the following acid-base reactions are reactions that we will study in greater detail in the chapters to follow. Propose the mechanism and then clearly label the acid, base, conjugate acid, and conjugate base: Add curved arrows to show the mechanism for the given reaction. 8.--8-- + OH= 13+ DO нан + H₂O, IU Z 0 a 60 Harrow_forward1. 1a) 1b) 1c) 1d) For each of the following reactions: Draw a reaction mechanism (curved arrows) and comeplete the reaction on the right side. Then predict which side of the equilibrium is favored, left, right or either. Circle the stronger acid. If the strength are euqal, circle both. Give one word from the HIRE rules to state the most important factor in your determination and put it in the box. O N SH + F3C OH + + _N_ + OH Oo. 8arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning