PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 17, Problem 17.50P
a. Explain why protonation of pyrrole occurs at
b. Explain why A is more acidic than C, the conjugate acid of pyridine.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The presence of a pi bond also makes a compound a base. With this in mind, draw the conjugate acid of ethylene, CH2=CH2.
Carboxylic Acid Derivatives
Resolve the reactions.
Explain why the pH of 0.1 M acetic acid (pH = 3) is higher than the pH of 0.1 M trifluoroacetic acid (pH = 1).
Chapter 17 Solutions
PKG ORGANIC CHEMISTRY
Ch. 17 - Prob. 17.1PCh. 17 - Problem 17.2 What orbitals are used to form the...Ch. 17 - Problem-17.3. Give the IUPAC name for each...Ch. 17 - Prob. 17.4PCh. 17 - Problem-17.5 What is the structure of propofol,...Ch. 17 - Problem 17.6 What is the structure of a compound...Ch. 17 - Problem 17.7 How many NMR signals does each...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Problem 17.14 Januvia, the trade name for...Ch. 17 - Prob. 17.15PCh. 17 - Problem 17.16 Rank the following compounds in...Ch. 17 - Problem 17.17 Draw the seven resonance structures...Ch. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Problem 17.22 How many NMR signals does ...Ch. 17 - 17.23 Name each compound and state how many lines...Ch. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 17 - 17.28 Draw a structure corresponding to each...Ch. 17 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 17 - Prob. 17.30PCh. 17 - Prob. 17.31PCh. 17 - Prob. 17.32PCh. 17 - 17.33 Label each compound as aromatic,...Ch. 17 - Prob. 17.34PCh. 17 - 17.35 Pentalene, azulene, and heptalene are...Ch. 17 - 17.36 The purine heterocycle occurs commonly in...Ch. 17 - Prob. 17.37PCh. 17 - 17.38
How many electrons does C contain?
How...Ch. 17 - Prob. 17.39PCh. 17 - 17.40 Explain the observed rate of reactivity of...Ch. 17 - 17.41 Draw a stepwise mechanism for the following...Ch. 17 - Prob. 17.42PCh. 17 - 17.43 Draw additional resonance structures for...Ch. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - 17.46 Which compound in each pair is the stronger...Ch. 17 - 17.47 Treatment of indene with forms its...Ch. 17 - Prob. 17.48PCh. 17 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 17 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - 17.53 How many signals does each compound...Ch. 17 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 17 - 17.55 Propose a structure consistent with each...Ch. 17 - 17.56 Propose a structure consistent with each...Ch. 17 - 17.57 Thymol (molecular formula ) is the major...Ch. 17 - 17.58 You have a sample of a compound of molecular...Ch. 17 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 17 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 17 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 17 - 17.62 Answer the following questions about...Ch. 17 - 17.63 Stanozolol is an anabolic steroid that...Ch. 17 - Prob. 17.64PCh. 17 - 17.65 Use the observed data to decide whether C...Ch. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - Prob. 17.68PCh. 17 - 17.69 Although benzene itself absorbs at in its ...
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
- Give the products of the following acid–base reactions and indicate whether reactants or products are favored at equilibrium. a.CH3COH + CH3O− b. CH3CH2OH + −NH2 c. CH3COH + CH3NH2 d. CH3CH2OH + HClarrow_forward3. a) Explain why the protonation of pyrrole occurs at C2 to form A, rather than the N atom to form B b) Explain why compound A is more acidic than C, the conjugate acid of pyridine. H H C2 +N -H Pyrrole pKa=0.4 pKa=5.3 A B C .Harrow_forwardThe pKa of ascorbic acid (vitamin C, page 55) is 4.17, showing that it is slightly more acidic than acetic acid (CH3COOH, pKa 4.74). Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.arrow_forward
- 4. Draw the structure and name the first ten (10) members of Acid Halides using bromine as the halide.arrow_forwarda. Explain why protonation of pyrrole occurs at C2 to form A, rather than on the N atom to form B. b. Explain why A is more acidic than C, the conjugate acid of pyridine.arrow_forward78) Why are primary alcohols more acidic than tertiary alcohols, in general? Because tertiary alcohols have less acidic hydrogens. Because primary alcohols have less electron-donating groups which create more effective charge separation between oxygen and hydrogen atom, making it more acidic. Because primary alcohols are more polar than tertiary alcohols. Because primary alcohols have less electron-donating groups which decrease electron density on oxygen, making it more susceptible for H+ to depart from the structure.arrow_forward
- Ethyne (HC‚CH) has a pKa value of 25, water has a pKa value of 15.7, and ammonia (NH3) has a pKa value of 36. Draw the equation, showing equilibrium arrows that indicate whether reactants or products are favored, for the acid–base reaction of ethyne with a. HO- . b. -NH2. c. Which would be a better base to use if you wanted to remove a proton from ethyne, HO- or -NH2?arrow_forwardDraw the products of each proton transfer reaction. Label the acid and base in the starting materials, and the conjugate and base in the products. а. СH,он + NH c. CH;CH2-0-H + H-Br b. CH;CH d. CH;C=C- + H2O + CH;O =arrow_forwardBriefly, but clearly, explain why the –OH hydrogen in acetic acid (CH3CO2H) is more acidic than in ethanol (C2H5OH).arrow_forward
- Predict the principal organic product of this reaction. HC CNa 1. liquid ammonia 2. H₂O+arrow_forwardProvide the product of reactionarrow_forwardOne step in the synthesis of lisinopril, a drug used to treat high blood pressure, involves the reaction of A with B in the presence of a reducing agent to form C. What is the structure of C?arrow_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 Learning
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY