Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 2.SE, Problem 41AP
The O-H hydrogen in acetic acid is more acidic than any of the C-H hydrogens. Explain this result using resonance structures.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Why is H3C-O-SİH3 ether a weaker base
than (CH3)3O?
Predict reagents needed to complete this E1 elimination reaction.
Br
3. Explain in 2 sentences why acetic acid is more acidic than butanoic acid.
Chapter 2 Solutions
Organic Chemistry
Ch. 2.1 - Prob. 1PCh. 2.1 - Prob. 2PCh. 2.1 - Use the electronegativity values shown in Figure...Ch. 2.1 - Look at the following electrostatic potential map...Ch. 2.2 - Ethylene glycol, HOCH2CH2OH, may look nonpolar...Ch. 2.2 - Make three-dimensional drawings of the following...Ch. 2.3 - Calculate formal charges for the nonhydrogen atoms...Ch. 2.3 - Organic phosphate groups occur commonly in...Ch. 2.6 - Which of the following pairs of structures...Ch. 2.6 - Draw the indicated number of resonance forms for...
Ch. 2.7 - Nitric acid (HNO3) reacts with ammonia (NH3) to...Ch. 2.8 - Prob. 12PCh. 2.8 - Amide ion, H2N-, is a much stronger base than...Ch. 2.9 - Prob. 14PCh. 2.9 - Prob. 15PCh. 2.9 - Prob. 16PCh. 2.11 - Using curved arrows, show how the species in part...Ch. 2.11 - Prob. 18PCh. 2.12 - Of the two vitamins A and C, one is hydrophilic...Ch. 2.SE - Prob. 20VCCh. 2.SE - The following model is a representation of...Ch. 2.SE - cis-l, 2-Dichloroethylene and trans-1,...Ch. 2.SE - The following molecular models are representations...Ch. 2.SE - Predict the product(s) of the acid/base reactions...Ch. 2.SE - Use curved arrows to draw the protonated form of...Ch. 2.SE - Prob. 26MPCh. 2.SE - Double bonds can also act like Lewis bases,...Ch. 2.SE - Prob. 28APCh. 2.SE - Use the electronegativity table given in Figure...Ch. 2.SE - Which of the following molecules has a dipole...Ch. 2.SE - Prob. 31APCh. 2.SE - Phosgene, C12C=O, has a smaller dipole moment than...Ch. 2.SE - Prob. 33APCh. 2.SE - Methanethiol, CH3SH, has a substantial dipole...Ch. 2.SE - Calculate the formal charges on the atoms shown in...Ch. 2.SE - Assign formal charges to the atoms in each of the...Ch. 2.SE - Which of the following pairs of structures...Ch. 2.SE - Prob. 38APCh. 2.SE - 1, 3-Cyclobutadiene is a rectangular molecule with...Ch. 2.SE - Alcohols can act either as weak acids or as weak...Ch. 2.SE - The O-H hydrogen in acetic acid is more acidic...Ch. 2.SE - Draw electron-dot structures for the following...Ch. 2.SE - Write the products of the following acid-base...Ch. 2.SE - Rank the following substances in order of...Ch. 2.SE - Which, if any, of the substances in Problem 2-44...Ch. 2.SE - The ammonium ion (NH4+, pKa = 9.25) has a lower...Ch. 2.SE - Prob. 47APCh. 2.SE - Prob. 48APCh. 2.SE - Calculate Ka values from the following pka’s:...Ch. 2.SE - Calculate pKa values from the following Ka’s:...Ch. 2.SE - What is the pH of a 0.050 M solution of formic...Ch. 2.SE - Prob. 52APCh. 2.SE - Maleic acid has a dipole moment, but the closely...Ch. 2.SE - Assume that you have two unlabeled bottles, one of...Ch. 2.SE - Identify the acids and bases in the following...Ch. 2.SE - Which of the following pairs represent resonance...Ch. 2.SE - Draw as many resonance structures as you can for...Ch. 2.SE - Carbocations, which contain a trivalent,...Ch. 2.SE - We’ll see in the next chapter that organic...Ch. 2.SE - The azide functional group, which occurs in...Ch. 2.SE - Phenol, C6H5OH, is a stronger acid than methanol,...Ch. 2.SE - Thiamin diphosphate (TPP), a derivative of vitamin...Ch. 2.SE - Determine if each compound or ion below has a...Ch. 2.SE - Prob. 64APCh. 2.SE - Prob. 65APCh. 2.SE - Draw the conjugate base for each compound below...Ch. 2.SE - 1, 1, 1-Trichloroethanol is an acid more than 1000...
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
- Although we normally think of acetic acid as an acid, it can also act as a weak base. Treated with a strong acid, it can become protonated. The conjugate acid of acetic acid is shown. H₂C :O-H H* Draw curved arrows for resonance structure 1. H₂C Derive a resonance structure for this ion which, taken with the given structure, would show that the two -OH groups are equivalent, the two C-O bonds are equivalent, and the positive charge is shared equally by the two oxygens. с The skeleton for the second resonance structure is provided. Add the bond(s), charge(s), and unshared pairs of electrons. Then draw the curved arrows to show the flow of electrons that transforms each resonance structure into the other. : OH || H3C- I.. -H OH :0 -H Complete the structure of resonance structure 2 and draw curved arrows to transform it to resonance structure 1. *K H₂C -C OH OHarrow_forwardWhich is more acidic? Explain your reasoning H3C, OH HO ČH3 2-methylpropanoic acid ethanoic acidarrow_forwardOH CH3 HNO3, H₂SO4 orarrow_forward
- 1) Answer the following questions using the table below: Acid Benzoic Acid, C6H5CO2H Benzylammonium ion, C6HSCH2NH3* Chloroacetic acid, CICH2CO2H Hydrogen Sulfide, H2S Ka 6.31 x 10-5 4.47 x 10-10 1.35 x 10-3 1.00 x 10-7 Nitrous Acid, HNO2 4.47 x 104 a) Which is the strongest acid? b) Which acid has the highest pH, and what is the chemical formula of the conjugate base? c) Write the reaction of nitrous acid (HNO2) acting as a Brønsted-Lowry acid in water and write the Ka expression.arrow_forward16. Draw significant resonance structures for the following compound. Which of this is/are most significant resonance structure(s)? Explain why. (a) مهم (b) the H H- (c)arrow_forwardPart G Give the IUPAC name for compound shown below. Spell out the full name of the compound. 2-methylheptanoic acid Submit Previous Answers Request Answer X Incorrect; Try Again Part H CH3 HC-CH2-CH-CH2-CH2-CH2-COOH OH CH3 CH3 -CH2-COOH Give the IUPAC name for compound shown below. Spell out the full name of the compound. HỌC CH–CH HC Submit Previous Answers Request Answer × Incorrect; Try Againarrow_forward
- O—CH,CH,CH HBrarrow_forwardDraw an expanded structural formula of pent-1-en-3-yne/ CH3-CC-CH=CH2 and then label each carbon. Indicate the longest and shortest C-H bond and predict the C—C single bond that has the highest BDE(bond dissociation energy).arrow_forwardWrite the systematic (IUPAC) name for each of the following organic molecules: structure OH CH3 C CH3 CH3 CH₂ CH3 CH3CH2C–CH2–CH2C−CH2CH3 CH3 CH2 OH CH3 CH3-CH₂ OH CH₂ CH3 CH3—CH,—CH–CH2–CH2–CH–CH2–CH-CH2CH3 namearrow_forward
- Compound A Compound F HCI CH3OH H₂SO4 Compound B CH3 CH₂ CH₂ Cl Compound E NaOH K₂Cr₂O7 H₂SO4 Compound C K₂Cr₂O7 H₂SO4 Compound D a. Draw the structural formulas of compounds A, C, D, E and F in the boxes provided above.arrow_forwardWhich is a correct resonance structure for compound A below: H2C=CH-C*H-CH=O (Compound A) 2. H2C=CH-CH=CH-O* 3. H2C=CH-c*H=CH-O I. H2C*-CH=CH-CH=O 4. H2C=C*H=CH-CH=DO O 3 and 4 O 2 and 3 O 1 and 4 01 and 2 MacBook A 20 F3 O00 F1 F2 F4 F5 F6 $ 2 6. Q W E Y S D F G T # 3arrow_forwardSelect the stronger acid from pair and explain your reasoning. For stronger acid, write a structural formula for its conjugate base. Q.) CH3CH2OH or CH3C=(three sticks in equals)CHarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY