Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 19.5, Problem 7P
Explain why cyclopentadiene (pKa = 15) is more acidic than pyrrole (pKa - 17), even though nitrogen is more electronegative than carbon.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Explain why cyclopentadiene (pKa = 15) is more acidic than pyrrole (pKa ∼17), even though nitrogen ismore electronegative than carbon.
Draw the structure of the predominant form of CF3CH2OH (pK a = 12.4) at pH = 6.
(NH4)3PO4
Pb(NO:)4
->
Pb3(PO4)4
NHẠNO3
Chapter 19 Solutions
Organic Chemistry (8th Edition)
Ch. 19.1 - Name the following:Ch. 19.2 - Prob. 3PCh. 19.2 - Prob. 4PCh. 19.3 - Draw the product of each of the following...Ch. 19.5 - Prob. 6PCh. 19.5 - Explain why cyclopentadiene (pKa = 15) is more...Ch. 19.5 - When pyrrole is added to a dilute solution of...Ch. 19.6 - Prob. 10PCh. 19.6 - How to the mechanisms of the following reactions...Ch. 19.6 - Prob. 12P
Ch. 19.6 - Rank the following compounds from easiest to...Ch. 19.7 - Prob. 14PCh. 19.7 - Prob. 15PCh. 19.7 - Prob. 16PCh. 19.7 - Prob. 17PCh. 19.7 - Prob. 18PCh. 19.7 - Prob. 19PCh. 19.7 - Prob. 20PCh. 19 - Name the following:Ch. 19 - Prob. 22PCh. 19 - Rank the following compounds from strongest acid...Ch. 19 - Which of the following compounds is easier to...Ch. 19 - Rank the following compounds from most reactive to...Ch. 19 - One of the following compounds undergoes...Ch. 19 - Benzene undergoes electrophilic aromatic...Ch. 19 - Pyrrole reacts with excess...Ch. 19 - The dipole moments of furan and tetrahydrofuran...Ch. 19 - Name the following:Ch. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - a. Draw resonance contributors to show why...Ch. 19 - The chemical shifts of the C-2 hydrogen in the...Ch. 19 - Explain why protonating aniline has a dramatic...Ch. 19 - Prob. 36PCh. 19 - Propose a mechanism for the following reaction:Ch. 19 - Prob. 38PCh. 19 - Propose a mechanism for the following reactions:Ch. 19 - Prob. 40PCh. 19 - Prob. 41PCh. 19 - Prob. 42PCh. 19 - Organic chemists work with tetraphenylporphyrins...Ch. 19 - Show how the following compounds can be prepared...
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
- (CH3)2C=CHCH2CH3 and Ozone (o)3 /Zn product?arrow_forwardTreatment of indene with NaNH2 forms its conjugate base in a Brønsted–Lowry acid–base reaction. Draw all reasonable resonance structures for indene’s conjugate base, and explain why the pKa of indene is lower than the pKa of most hydrocarbons.arrow_forwardTreatment of indene with NaNH2 forms its conjugate base in a Brønsted– Lowry acid–base reaction. Draw all reasonable resonance structures for indene's conjugate base, and explain why the pKa of indene is lower than the pKa of most hydrocarbons.arrow_forward
- (c) Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluorophenol.arrow_forwardConjugate base acid Cyclopentadiene pKa 1) Consider the reaction AH(+) + H₂O →> A:+H3O+. For the following named acids: 1) draw the structure of the acid, 2) give the approximate pKa of the conjugate acid (±1 pKa unit), 3) give the name of the conjugate base, and 4) draw the structure of the conjugate base. For the purposes of answering this question you may use pKa values evenly divisible by 5. p-Methoxyanilinium cation pKa Benzenesulfonic acid Butanal pKa pKaarrow_forwardDraw a resonance structure of the acetonitrile anion, :CH2C =N, and account for the acidity of nitriles.arrow_forward
- The enamine prepared from acetone and dimethylamine is shown here in its lowest-energy form. (a) What is the geometry and hybridization of the nitrogen atom? (b) What orbital on nitrogen holds the lone pair of electrons? (c) What is the geometric relationship between the p orbitals of the double bond and the nitrogen orbital that holds the lone pair? Why do you think this geometry represents the minimum energy?arrow_forwardCalculate ΔH° for the rate-determining step of the reaction of CH4 with I2. Explain why this result illustrates that this reaction is extremely slow.arrow_forwardCompare and contrast the physical and chemical properties of: • propan-1-ol and propan-2-ol; • (E)-butenedioic acid (fumaric acid) and (Z)-butenedoic acid (maleic acid)arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY