Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 3, Problem 43P
The compound at right has (for obvious reasons) been given the trivial name squaric acid. Squaric acid is a diprotic acid, with both protons being more acidic than acetic acid. In the dianion obtained after the loss of both protons, all of the carbon–carbon bonds are the same length as well as all of the carbon-oxygen bonds. Provide a resonance explanation for these observations.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Like nitrogen and carbon, oxygen also shows this same hybridization effect on acidity. Both of the following compounds can lose a proton from a positively charged oxygen with three bonds to give a conjugate base containing neutral oxygen with two bonds. One of these structures has pKa = -2.4, while the other has pKa = -8.0. Show the reaction of each compound with water.
Arrange the following acids in order of decreasing acidity. Justify your choices, making sure to use the space below to analyze each compound and determine the factor(s) contributing to the acidity. Lone pairs and formal charges are not provided. Include resonance structures where appropriate; do not forget to draw lone pairs and formal charges as
necessary.
Why is it not possible to predict whether H3PO4 or H2SO3 is the stronger acid? Show how you can use data to decide which is the stronger acid.
Chapter 3 Solutions
Organic Chemistry
Ch. 3 - Prob. 1PPCh. 3 - PRACTICE PROBLEM 3.2
Write equations showing the...Ch. 3 - PRACTICE PROBLEM 3.3 Which of the following are...Ch. 3 - Prob. 4PPCh. 3 - PRACTICE PROBLEM 3.5 Formic acid (HCO2H) has...Ch. 3 - Prob. 6PPCh. 3 - Prob. 7PPCh. 3 - Prob. 8PPCh. 3 - PRACTICE PROBLEM 3.9 Predict the outcome of the...Ch. 3 - Prob. 10PP
Ch. 3 - Prob. 11PPCh. 3 - Prob. 12PPCh. 3 - Prob. 13PPCh. 3 - Prob. 14PPCh. 3 - PRACTICE PROBLEM 3.15 Nitro groups have a large...Ch. 3 - PRACTICE PROBLEM 3.16
Your laboratory instructor...Ch. 3 - Prob. 17PPCh. 3 - Prob. 18PPCh. 3 - Prob. 19PPCh. 3 - What is the conjugate base of each of the...Ch. 3 - List the bases you gave as answers to Problem 3.20...Ch. 3 - 3.22 What is the conjugate acid of each of the...Ch. 3 - List the acids you gave as answers to Problem 3.22...Ch. 3 - Rank the following in order of increasing acidity.Ch. 3 - Without consulting tables, select the stronger...Ch. 3 - Designate the Lewis acid and Lewis base in each of...Ch. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Write an equation, using the curved-arrow...Ch. 3 - 3.30 What reaction will take place if ethyl...Ch. 3 - 3.31 (a) The of formic acid. What is the? (b)...Ch. 3 - Acid HA has pKa=20; acid HB has pKa=10. (a) Which...Ch. 3 - Prob. 33PCh. 3 - 3.34 (a) Arrange the following compounds in order...Ch. 3 - 3.35 Arrange the following compounds in order of...Ch. 3 - 3.36 Arrange the following in order of increasing...Ch. 3 - Prob. 37PCh. 3 - 3.38 Supply the curved arrows necessary for the...Ch. 3 - Glycine is an amino acid that can be obtained from...Ch. 3 - 3.40 Malonic acid, , is a diprotic acid. The for...Ch. 3 - 3.41 The free-energy change, , for the ionization...Ch. 3 - 3.42 At the enthalpy change, , for the ionization...Ch. 3 - The compound at right has (for obvious reasons)...Ch. 3 - 3.44.
(a) Given the above sequence of...Ch. 3 - Prob. 45PCh. 3 - Prob. 46PCh. 3 - 3.47 As noted in Table 3.1, the of acetone, , is...Ch. 3 - Formamide (HCONH2) has a pKa of approximately 25....Ch. 3 - List all the chemical species likely to be present...Ch. 3 - Prob. 2LGPCh. 3 - Prob. 3LGPCh. 3 - Prob. 4LGP
Additional Science Textbook Solutions
Find more solutions based on key concepts
APPLY 1.2 Express the following quantities in scientific notation
using fundamental SI units of mass and lengt...
CHEMISTRY-TEXT
The cover plate of a flat-plate solar collector is at 15°C, while ambient air at 10°C is in parallel flow over ...
Fundamentals of Heat and Mass Transfer
Determine [OH], [H+], and the pH of each of the following solutions. a. 1.0 M KCl b. 1.0 M KC2H3O2
Chemistry
Practice Exercise 2
By using a conversion factor from the back inside cover, determine the length in kilometer...
Chemistry: The Central Science (14th Edition)
Which of the following are not acids? CH3COOH CO2 HNO2 HCOOH CCl4
Essential Organic Chemistry (3rd Edition)
___________________________________________________
65. Determine the molecular geometry of each molecule.
(a) ...
Introductory Chemistry (6th Edition)
Knowledge Booster
Learn more about
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
- Compare with explanation the acidity of the following pairs of compounds. (Note: You must draw the appropriate resonance structures to support your answers.) (c) (i) .COOH .COOH H3COarrow_forwardYou will not find “hydroxide” in the stockroom, but you will find sodium hydroxide (NaOH) andpotassium hydroxide (KOH). Lithium hydroxide (LiOH) is expensive and used in spacecraft airfilters since hydroxide reacts with carbon dioxide, and lithium is lighter than sodium or potassium.Cesium and francium hydroxides are very expensive and little used. Is this information consistentwith your answer to the previous question?arrow_forwardSalicylic acid, HOC6H4CO2H, and its derivatives have been used as pain relievers for a long time. Salicylic acid occurs in small amounts in the leaves, bark, and roots of some vegetation (most notably historically in the barkof the willow tree). Extracts of these plants have been used as medications for centuries. The acid was first isolated in the laboratory in 1838.(a) Both functional groups of salicylic acid ionize in water, with Ka = 1.0 × 10−3 for the—CO2H group and 4.2 × 10−13 for the −OH group. What is the pH of a saturated solution of the acid (solubility = 1.8 g/L).(b) Aspirin was discovered as a result of efforts to produce a derivative of salicylic acid that would not be irritating to the stomach lining. Aspirin is acetylsalicylic acid, CH3CO2C6H4CO2H. The −CO2H functional group is stillpresent, but its acidity is reduced, Ka = 3.0 × 10−4. What is the pH of a solution of aspirin with the same concentration as a saturated solution of salicylic acid (See Part a).(c) Under some…arrow_forward
- Sulfuric acid (H2SO4) has a pKa value of -10 and it is almost completely ionized in water. Write the ewis structure for the conjugate base of sulfuric acid. Draw all the possible resonance structures for the corresponding conjugate base.arrow_forwardHow is the resonance form of Acid Orange, drawn below, obtained? Redraw the molecule and show all arrows in your rationale. NaO3S HN-N=arrow_forwardList the bond lenghts between the carbon and the oxygen atoms for the carboxylic acid and carboxylate ion and rank from shortest to longest. carboxylic acid carboxylate ion c-o c=o provide an explanation for the differences in the bond lengths and the orientation of the dipole moment between the acid and ion.arrow_forward
- Would CH3NH3C2H3O2 (salt) be neutral, basic, acidic or cannot be determined?arrow_forwardPredict the stronger acid in each pair: benzoic acid (C6H5COOH) or phenol (C6H5OH).arrow_forwardSalicylic acid, HOC6H4CO2H, and its derivatives have been used as pain relievers for a long time. Salicylic acid occurs in small amounts in the leaves, bark, and roots of some vegetation (most notably historically in the bark of the willow tree). Extracts of these plants have been used as medications for centuries. The acid was first isolated in the laboratory in 1838. (a) Both functional groups of salicylic acid ionize in water, with Ka = 1.0 ×× 10−3 for the—CO2H group and 4.2 ×× 10−13 for the −OH group. What is the pH of a saturated solution of the acid (solubility = 1.8 g/L). (b) Aspirin was discovered as a result of efforts to produce a derivative of salicylic acid that would not be irritating to the stomach lining. Aspirin is acetylsalicylic acid, CH3CO2C6H4CO2H. The −CO2H functional group is still present, but its acidity is reduced, Ka = 3.0 ×× 10−4. What is the pH of a solution of aspirin with the same concentration as a saturated solution of salicylic acid (See Part a).arrow_forward
- What is the reasoning behind F3CCOOH being less acidic? Although bromine is larger than fluorine and therefore would have greater acidity, is it because there are 3 fluorines compared to 1 bromine (so the pull is greater)?arrow_forwardThe hydride ion is very basic and reacts readily with compounds having even weakly acidic protons to form H2. True or false?arrow_forwardThe structure of Vitamin C (ascorbic acid) is shown below. As the name indicates, the molecule is somewhat acidic. Actually, one of the hydrogens on the four OH groups is much more acidic than the other three ones. Which one is the acidic hydrogen? Hints: To find the answer, you will again have to draw some resonance structures of the product formed after loss of H+. Consider the product after the loss of H+ for each of the OH groups. Only two of the OH groups have resonance structures after deprotonation; one of these two groups has a much better resonance structure than the other one (again after deprotonation). Note that the oxygen atom that is part of the five-membered ring has nothing to do with the problem.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY