The pK, value for a protonated amine (R3NH*) dependson the number of alkyl groups attached to N, as shownhere. This order disagrees with what we would predictusing charge stability.(a) From least acidic to most acidic, what is the orderCH3ONH,NH3H3CH3CON.HạC H CH3`CH3pKa = 9.2510.6610.739.81that would be predicted using charge stability?(b) Can you explain the reason for the discrepancy? Hint: These pK, values are all measured in water.

(a) The stability of a positively charged species depends on the groups attached to the positively…

Answered: The pK, value for a protonated amine…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter20: Acidity And Pka Of Phenols

Section: Chapter Questions

Problem 9E

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Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. (a) (b) (c) (d)
The following are equivalent ways of asking about the acidity of an H atom: • What is the most acidic H on the molecule? • Which H is associated with the published pKa value? • Which H on the molecule is easiest to remove? • Which H on the molecule takes the least energy to remove? • Which bond to an H is most polarized? • For which H atom is removal least uphill in energy? • Which bond to an H atom, when broken, results in the lowest PE conjugate base? We will often find the last of these questions is easiest to answer. To do this, find all the different Hatoms on the molecule, and draw all possible conjugate bases.Only the lowest-energy one is the “real” conjugate base. Identify this structure, and you have found the most acidic H. Use this strategy to find the most acidic H on each of the following molecules. Note: Each structure hasat least three different kinds of H’s, so draw at least three unique conjugate bases for each.
Summarize the relationship between pKa and acid strength by completing the following sentences: a. The higher the pKa of an acid, the stronger or weaker the acid. b. The lower the pKa of an acid, the stronger or weaker the acid.
Rank the following conjugate bases in order of decreasing basicity, putting the most basic first. H2C=CH HC=C CH3 II Multiple Choice || > |> |II |> || > III III > || > | III > | > ||
As we will see in later chapters, many steps in key reaction sequencesinvolve acid–base reactions. (a) Draw curved arrows to illustrate the flow of electrons in steps [1]–[3]. (b) Identify the base and its conjugate acid in step [1]. (c) Identify the acid and its conjugate base in step [3].
1. Identify the acids and bases in the following reactions: (a) CH3OH + H+ CH3OH2+ (b) СН3ОН + NН2 CH30- + NH3 (c) ZnCl2 || || + ZnCl2 H3C° H. H3C H.
3. For the following acid - base reaction, (a) predict the products; (b) identify the Bronsted acid, Bronsted base, conjugate acid, and conjugate base; (c) use curved arrows to show the flow of electron pairs in the reaction. CH3 CH2C-OH + NaNHa
What is the increasing order of basicity among the following compounds ? NH NH NH OH OH OH II III IV O1< || < III < IV OIV < III < || < | OI< II < || < IV OIl
3) а) decreasing acidity and explain your answer. CHCHNΗ Arrange the following compounds in order of CH,CH,OH CH,CH,CH, b) part (a) in order of increasing basicity and explain your Arrange the conjugate bases of the acids given in answer.
b My Questions | bartleby O Dashboard O Course: Chem 120 - Organic Che X O LOCAL clicker + -> A cpp.edu/~Isstarkey/local/clicker/bonding/acid-base.html What is the most acidic proton in methanol, CHOH Which is the stronger base? Explain briefly. (H, or H,)? Explain briefly (CB = Conjugate Base). NH3 NH2 H-0-C-H H. ammonia aniline A) H, is more acidic. Because carbon is less clectronegative, CB-b is more stable than CB-a. A) Because this is more stable: aniline is the stronger base. -NH2 B) H, is more acidic. Because carbon is less electronegative, H, is more stable than Hp- B) Because this is more stable: ammonia is the stronger base. -NH2 C) H, is more acidie. Because oxygen is more electronegative, CB-a is more stable than CB-b. C) Because this is more stable: NH3 aniline is the stronger base. D) H, is more acidic. Because oxygen is more electronegative, H, is more stable than Hp. D) Because this is more stable: NH2 ammonia is the stronger base. E) H, is more acidic. Because oxygen…
Proivde your view on this "The acidity of HA increases when the conjugate base A:− is resonancestabilized" ?
H2SO4 + NH3 ==== HSO4- + NH4+ . Which of the products is a conjugate base?

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