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 6.18YT
Interpretation Introduction
Interpretation:
The difference in pKa between the protonated and uncharged
Concept introduction:
Generally, the charged species is significantly higher in energy and thus less stable than its uncharged species. A proton is significantly more acidic when the atom to which it is attached is positively charged than when that atom is uncharged. The pKa value of charged species is less as compared to uncharged species. The less pKa value means more acidic species.
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[References]
Answer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D below each structure. The pKa's for the acids of interest are: acetic acid (pK,
4.8), and hydrogen bromide (pK,=-9).
CH3
Br
CH3
H-Br
OH
B
acetic acid
bromide
acetate
hydrogen bromide
a) The stronger base is
b) Its conjugate acid is
c) The species that predominate at equilibrium are (two letters, e.g. ac)
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Answer questions a-c about the Bronsted acid-base reaction below using the Q41
identifying letters A-D below each structure.
A table of pk, values for various organic and inorganic acids can be found in the
references section.
NH₂
A
amide
B
ethyl acetate
CH₂
NH3
C
ammonial
+
I
CH₂
D
ethyl acetate
enolate
a) The weaker acid is
b) Its conjugate base is
c) The species that predominate at equilibrium are (two letters, e.g. AC)
8. Draw the structures of the conjugate acid and base for the following reaction. Provide
the mechanism for their formation using curved arrows.
pK
-17
-35
conjugate acid
conjugate base
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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- 1) Consider the reaction AH+ H₂O A:+H3O¹. For the following named acids: 1) draw the structure of the acid, 2) give the approximate pKa value of the acid in multiples of 5, 3) give the name of the conjugate base, and 4) draw the structure of the conjugate base. m-Chlorophenol 3-Pentanone acid Conj. base acid Conj. base pKa Benzoic acid pka_ iso-Butyl ammonium ion pka_ Diethyl Malonate pka_ Benzyl oxonium ion pka_ 1-pentyne pKa pKa Ethyl Acetate pKaarrow_forward14. Rank the indicated protons in order of decreasing acidity. HOT TeH 2 IZ 3 SeH-5arrow_forwardWhich of the following statements are TRUE for molecule below? i iv H2N, но. NH i H2N NH General pKa values: Protonated amines (with a positive charge): 9-11 Alcohols: 15-17 Carboxylic acids: 3-5 O This molecule will have a net charge of 0 at pH=7 O This molecule will have a net charge of +1 at pH=7 This molecule will have a net charge of +2 at pH=2 i is more basic than ii due to resonance O iv is more acidic than v due to resonancearrow_forward
- Rank the following molecules according their acidity. (1 = lowest pka) OEt O 요 ii iiNet il 요 NEt₂ O O CF 3 Predict how the highest pka from question 9 compares with the lowest pka from question 8.arrow_forwardUsing the pk, table, estimate pk, values for the most acidic group on the compounds below, and draw the structure of the conjugate base that results when this group donates a proton. Use the pka table above and/or from the Reference Tables. a) b) O. O H OH O O -NH₂ -NH₂ Answer a. The most acidic group is the protonated amine, pka ~ 5-9 b. Alpha proton by the C=O group, pka ~ 18-20 c. Thiol, pka 10 d. Carboxylic acid, pka ~ 5 e. Carboxylic acid, pka ~ 5 c) OH H₂N SH NH₂ OH asparagine H lysergic acid. OH N H CH3 Can someone please explain these answers. Including which protons being compared on the compound.arrow_forwardAnswer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D below each structure. A table of pK, values for various organic and inorganic acids can be found in the references section. CH3- CH3 но HO HO. OH acetic acid bicarbonate acetate carbonic acid a) The weaker base is b) Its conjugate acid is c) The species that predominate at equilibrium are (two letters, e.g. AC)arrow_forward
- 2. Show the structures of the missing substance(s) in each of the following acid-base equilibria. Write your answers in the blank space of the missing substance(s). Example: CH,-CH,-NH, CH;-CH,–NH, + H,0 = + OH (ANSWER) -NH, + H,O = -NH, а. (ANSWER) + H,0 = CH;-CH–NH,-CH, + OH b. (ANSWER) Diethylamine + H0= C. (ANSWER) (ANSWER)arrow_forward10. Rank the following in order of acidity of their -OH group (1-4: 1 for strongest) Explain the reasoning for your answr. Do not say" because of their pKa values!" You need to use ARIO and solvation to explain the reason underlying their relative_pKa values 10.a он OH он он CI 10b. ОН ОН OH OHarrow_forwardA ka of weak acid is 1 E-6, this means that For 1 million unionized acid, there is just one molecule is ionized .a O The concentration of hydronium ion equals the square root of its pKa value .b O For 1 million ionized acid, there is just one molecule is unionized .c O The concentration of hydroxyl ion equals the square root of its pka value .d Oarrow_forward
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