Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 6, Problem 6.12P
Interpretation Introduction
Interpretation:
Energy diagram similar to Figure 6-6, using
Concept introduction:
A proton is significantly more acidic when the atom to which it is attached is more positively charged than when it is uncharged. The charged species are much higher in energy than the uncharged species, in the sense that the charged species are significantly less stable. Out of the two species, the one with a higher pKa value indicates a weaker acid than the one with a lower pKa value.
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In each reaction, Label the reactants as a Lewis base (nucleophile) or a Lewis acid
(electrophile). Use curved arrows to show the movement of electron pairs in the reaction.
NH,
H-C-
H-
H.
ONH3
For the following acid-base reaction, predict which side of the equilibrium is favored.
F3C
он
HO,
F3C
Based on the following equilibrium
H++ HCO3- ↔ H2CO3
A)State what would happen if we added HCl to the reaction
B) State what would happen if we added NaOH to the reaction.
Chapter 6 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 6 - Prob. 6.1PCh. 6 - Prob. 6.2PCh. 6 - Prob. 6.3PCh. 6 - Prob. 6.4PCh. 6 - Prob. 6.5PCh. 6 - Prob. 6.6PCh. 6 - Prob. 6.7PCh. 6 - Prob. 6.8PCh. 6 - Prob. 6.9PCh. 6 - Prob. 6.10P
Ch. 6 - Prob. 6.11PCh. 6 - Prob. 6.12PCh. 6 - Prob. 6.13PCh. 6 - Prob. 6.14PCh. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Prob. 6.17PCh. 6 - Prob. 6.18PCh. 6 - Prob. 6.19PCh. 6 - Prob. 6.20PCh. 6 - Prob. 6.21PCh. 6 - Prob. 6.22PCh. 6 - Prob. 6.23PCh. 6 - Prob. 6.24PCh. 6 - Prob. 6.25PCh. 6 - Prob. 6.26PCh. 6 - Prob. 6.27PCh. 6 - Prob. 6.28PCh. 6 - Prob. 6.29PCh. 6 - Prob. 6.30PCh. 6 - Prob. 6.31PCh. 6 - Prob. 6.32PCh. 6 - Prob. 6.33PCh. 6 - Prob. 6.34PCh. 6 - Prob. 6.35PCh. 6 - Prob. 6.36PCh. 6 - Prob. 6.37PCh. 6 - Prob. 6.38PCh. 6 - Prob. 6.39PCh. 6 - Prob. 6.40PCh. 6 - Prob. 6.41PCh. 6 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - Prob. 6.44PCh. 6 - Prob. 6.45PCh. 6 - Prob. 6.46PCh. 6 - Prob. 6.47PCh. 6 - Prob. 6.48PCh. 6 - Prob. 6.49PCh. 6 - Prob. 6.50PCh. 6 - Prob. 6.51PCh. 6 - Prob. 6.52PCh. 6 - Prob. 6.53PCh. 6 - Prob. 6.54PCh. 6 - Prob. 6.55PCh. 6 - Prob. 6.56PCh. 6 - Prob. 6.57PCh. 6 - Prob. 6.58PCh. 6 - Prob. 6.59PCh. 6 - Prob. 6.60PCh. 6 - Prob. 6.61PCh. 6 - Prob. 6.62PCh. 6 - Prob. 6.63PCh. 6 - Prob. 6.64PCh. 6 - Prob. 6.65PCh. 6 - Prob. 6.66PCh. 6 - Prob. 6.67PCh. 6 - Prob. 6.68PCh. 6 - Prob. 6.69PCh. 6 - Prob. 6.70PCh. 6 - Prob. 6.71PCh. 6 - Prob. 6.72PCh. 6 - Prob. 6.73PCh. 6 - Prob. 6.74PCh. 6 - Prob. 6.75PCh. 6 - Prob. 6.76PCh. 6 - Prob. 6.77PCh. 6 - Prob. 6.78PCh. 6 - Prob. 6.79PCh. 6 - Prob. 6.80PCh. 6 - Prob. 6.81PCh. 6 - Prob. 6.82PCh. 6 - Prob. 6.83PCh. 6 - Prob. 6.84PCh. 6 - Prob. 6.85PCh. 6 - Prob. 6.86PCh. 6 - Prob. 6.87PCh. 6 - Prob. 6.88PCh. 6 - Prob. 6.1YTCh. 6 - Prob. 6.2YTCh. 6 - Prob. 6.3YTCh. 6 - Prob. 6.4YTCh. 6 - Prob. 6.5YTCh. 6 - Prob. 6.6YTCh. 6 - Prob. 6.7YTCh. 6 - Prob. 6.8YTCh. 6 - Prob. 6.9YTCh. 6 - Prob. 6.10YTCh. 6 - Prob. 6.11YTCh. 6 - Prob. 6.12YTCh. 6 - Prob. 6.13YTCh. 6 - Prob. 6.14YTCh. 6 - Prob. 6.15YTCh. 6 - Prob. 6.16YTCh. 6 - Prob. 6.17YTCh. 6 - Prob. 6.18YTCh. 6 - Prob. 6.19YTCh. 6 - Prob. 6.20YT
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Draw an energy diagram for the Brønsted–Lowry acid–base reaction of CH3CO2H with -OC(CH3)3 to form CH3CO2-and (CH3)3COH. Label the axes, starting materials, products, ?H°, and Ea. Draw the structure of the transition state.arrow_forwardin e 10 C N g For the following reaction, draw the Lewis Dot structure for each reactant and product including any formal charges. Also identify the Lewis Acid and the Lewis Base for this reaction. CH3CH2CCH+ NH2 -> CH3CH₂CC + NH3 On the product side of the equation, one of the C atoms has 1 unshared pair of electrons and is (-) charged.arrow_forwardNaHCO3 can deprotonate benzoic acid but cannot deprotonate phenol. On the other hand, NaOH can deprotonate both benzoic acid and phenol. Given this information, rank the molecules numbered I to V in order of decreasing acidity. COH cOH он H,0 H,CO, IV CH3 II I II (A) V > II >I > III > IV (В) II > 1 > V > III IV (C) II > V >I > IV > IIarrow_forward
- This example demonstrates how pk, can be used to help determine the favorability of a reaction. Keq is the equilibrium constant and is usually referred to as K₁ in acid-base reactions. Given the pK, of an acid, you can calculate K by taking its antilog. Species H₂O HCO3 H₂CO3 H₂O+ HCO3 + H₂O = base acid pK₁ 15.74 10.33 6.35 -1.74 Complete the balanced equations for the equilibria given in reaction 1 and reaction 2. Then use the pK₂ values in the table to calculate Keq for each reaction, where the Keq expression includes [H₂O]. Be sure to enter Keq in proper scientific notation. Reaction 1: Bicarbonate (acting as a base) reacts with water (acting as an acid). Kca =arrow_forwardWhich structure is a reasonable intermediate for this hydrolysis reaction? H;SO, H-0 HO OHarrow_forwardFor each equilibrium, label the stronger acid, stronger base, weaker acid and weaker base. For each reaction(s), does the position of equilibrium lie toward the right or left? H3PO4 + OH- ⇌ H2PO4- + H2O H2O + Cl- ⇌ HCl + OHarrow_forward
- 5. sy For each reaction, identify the acid, base, conjugate acid, and conjugate base. Determine which direction the reaction will favor. Ka H₂SO3 = 1.54 x 10-2 and 1.07 x 10-7 Kb of CH3NH₂ = 4.4 x 10-4 Ka of CH3OH = 3.20 x 10-16 a. CH3O+ NH3 CH3OH + NH₂ b. HSO3 + CH3NH2 H₂SO3 + CH3NH3* c. 2HF + Ca(OH)2 2H₂O + CaF2arrow_forwardTE Which is the strongest acid? OCarbonic acid 4.3 x 10 OCitric acid K=7.4 x 10 -4 Cyanic acid K2-3.5 x 10-4 OChloroacetic acid Ka = 1.4 x 10-3 Chlorous acid K = 1.1 x 10-2arrow_forwardConsider the acid-base reaction below: Ca(HCO3)2 + Ca(OH)2 ----> Compound A + H2O (OR Ca(HCO3)2 + Ca left parenthesis OH right parenthesis 2 ----> Compound A + H2O) One of the single ions that is used to form compound A is ____.arrow_forward
- A research student is trying to deprotonate A with t-butyllithium (shown above the arrow) which is a strong base to make anion B, however this desired deprotonation was not successful. Which of the following statements explains why the reaction failed? Li (CH3)2CHOH (solvent) A O t-butyl lithium is not a strong enough base to deprotonate A O the proton the student is trying to remove is not the most acidic proton in A O A will deprotonate the t-butyl lithium, rather than the other way around The active base in solution will be (CH3)2CHO` which is not a strong enough base to deprotonate Aarrow_forward. Which of the following reactions is a CORRECT representation for the neutralization of acetic acid by sodium hydroxide? (c) а) H Он H20 b) CH3Cоон + ОН CH3CO0 H20 c) CH3COOH + NaOH = NACH3C00 + H20 d) CHзCOон + Na он CH3CO0 Na H20 + +arrow_forwardFigine CH3 too CH₂ CH3 A 5-6 to NI H₂ No B CH3 CH₂ с CH3 O=C Oarrow_forward
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