Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 21, Problem 37P
Interpretation Introduction
Interpretation: The reason as to why the
Concept introduction: The more easily an acid loses proton, the more it will be acidic. In case of organic compounds, various factors help to determine the strength of acidity. Acidic strength can be measured by a factor known as
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PQ-3. What is the major product of this reaction?
(A)
CN
H
(B)
CN
O
CN
CN
H
(D)
HCN
OH
CN
Given that pKa for phenol is 9.95 and pKą for the ammonium ion is 9.24, will the following reaction be
favorable? (Will the products be favored at equilibrium?)
OH
+ NH3
phenol
pKa = 9.95
ammonia
phenoxide ion
ammonium ion
pKa = 9.24
Given that pKa for phenol is 9.95 and pKa for the ammonium ion is 9.24, will the following reaction be
favorable? (Will the products be favored at equilibrium?)
HO
+ NH3
phenoxide ion
phenol
pKa = 9.95
ammonia
ammonium ion
pKa = 9.24
Chapter 21 Solutions
Organic Chemistry (6th Edition)
Ch. 21.2 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 21.2 - Problem 23.3 When phenylacetaldehyde is dissolved...Ch. 21.3 - Prob. 5PCh. 21.3 - Problem 23.5 Which bonds in the following...Ch. 21.3 - Prob. 7PCh. 21.3 - Prob. 8PCh. 21.3 - Prob. 9PCh. 21.4 - Prob. 10PCh. 21.5 - Prob. 11PCh. 21.7 - Problem 23.11 Draw the products of each...
Ch. 21.7 - Problem 23.12 Draw the products of each reaction....Ch. 21.7 - Prob. 14PCh. 21.7 - Prob. 15PCh. 21.8 - Prob. 16PCh. 21.8 - Prob. 17PCh. 21.8 - Prob. 18PCh. 21.8 - Problem 23.18 How can pentan-2-one be converted...Ch. 21.8 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 21.9 - Problem 23.20 Which of the following compounds...Ch. 21.9 - Problem 23.21 Draw the products of each...Ch. 21.9 - Prob. 23PCh. 21.9 - Prob. 24PCh. 21.9 - Prob. 25PCh. 21.10 - Prob. 26PCh. 21.10 - Prob. 27PCh. 21.10 - Prob. 28PCh. 21.10 - Prob. 29PCh. 21 - 23.29 Draw enol tautomer(s) for each compound....Ch. 21 - 22.30 The cis ketone A is isomerized to a trans...Ch. 21 - 23.31 Draw enol tautomer(s) for each compound.
...Ch. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - 23.35 Rank the labeled protons in each compound in...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - 23.38 Acyclovir is an effective antiviral agent...Ch. 21 - 23.39 Explain why forms two different alkylation...Ch. 21 - Prob. 40PCh. 21 - 23.42 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - 23.45 Devise a synthesis of valproic acid , a...Ch. 21 - Prob. 57PCh. 21 - 23.57 Draw a stepwise mechanism showing how two...Ch. 21 - 23.58 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 65PCh. 21 - 23.66 Synthesize (Z)-hept-5-en-2-one from ethyl...
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- The following pKa values have been measured. Explain why a hydroxyl group in the para position decreases the acidity while a hydroxyl group in the meta position increases the acidity.arrow_forwardThioglycolic acid, HSCH2CO2H, a substance used in depilatory agents (hair removers) has pKa = 3.42. What is the percent dissociation of thioglycolic acid in a buffer solution at pH = 3.0?arrow_forwardTwo other commonly used sulfonic acids are methanesulfonic acid (CH3SO3H) and triuoromethanesulfonic acid (CH3SO3H). Which has the weaker conjugate base? Which conjugate base is the better leaving group? Which of these acids has the higher pKa?arrow_forward
- Two other commonly used sulfonic acids are methanesulfonic acid (CH3SO3H) and trifluoromethanesulfonic acid (CH3SO3H). Which has the weaker conjugate base? Which conjugate base is the better leaving group? Which of these acids has the higher pKa?arrow_forwardExplain why phenol (C6H50H) is substantially more acidic than methanol (CH3OH), but benzoic acid (C6H5CO2H) is not much more acidic than acetic acid (CH3CO2H). Нас — ОН ОН H3C- ОН OH pKa = 15.5 pKa = 10.0 pk = 4.75 pk = 4.2arrow_forwardPQ-12. What is the major product of this reaction? Н (В) ОН 1) LiAIH4, Et2O 2) H30+ (D) ОНarrow_forward
- Which is more acidic, p-methylphenol or phenol? why? Why is water more acidic than ethanol but slightly less acidic than methanol? Explain the acidity trend of alcohols: 1>2 > 3arrow_forwardPhenol has a pka = 10.0. 4-Hydroxybenzaldehyde has a pka = 7.3. Draw resonance forms of the conjugate base of both and explain why 4-hydroxybenzaldehyde is more acidic. (Acidic H is underlined.) OH phenol OH -H* - H* 4-hyroxybenzaldehydearrow_forwardPQ-23. What are the major products of this reaction? (A) i 18ОН ОН > (B) (D) 180 i Å CH 3 + NaOH (aq) 18ОН OHarrow_forward
- PQ-27. What is the major product of this reaction? (A) (C) (A) HO (C) OCH3 LOCH 3 OCH3 PQ-28. What is the major product of this reaction? O OH OH H3CH₂C CH₂CH3 O (B) (D) (B) (D) OCH3 LOH OCH3 OH O HO HQ CH₂CH3 CH3OH 1) CH3CH₂MgBr 2) NHÀ OH cess CH₂Liarrow_forwardRank the following carbonyls according to their electrophilicity (1 = most) OEt O of O NEt₂ O CF3 Oarrow_forwardExplain why p-nitrophenol (the left molecule) is more acidic than p-methylphenol (the right molecule). OH OH OH NO₂ CH3 pk = 7.14 pk = 9.95 = 10.19 a pkaarrow_forward
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