Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 22, Problem 22.75AP
Interpretation Introduction
(a)
Interpretation:
The conjugate acid structure of the two given compounds
Concept introduction:
The basicity of the compound depends upon the stability of its conjugate acid. The more stable the conjugate acid, the more basic the given compound. It also depends on the charge, inductive effects, the role of atom present, resonance, orbitals.
Interpretation Introduction
(b)
Interpretation:
The conjugate acid structure of tropone is to be predicted. The reason as to why the basicity of tropone is basic unusually is to be stated.
Concept introduction:
The basicity of the compound depends upon the stability of its conjugate acid. The more stable the conjugate acid, the more basic the given compound. It also depends on the charge, inductive effects, the role of atom present, resonance, orbitals.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Arrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenol
(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is
formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the
structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it
is dispensed under strict controls because it also causes birth defects.
PPha
NaOCH,CH3
HO-
isotretinoin
HO
A
Br
X
Y
19.48 Phthalic acid and isophthalic acid have protons on two carboxy groups
that can be removed with base. (a) Explain why the pKa for loss of the
first proton (pKa1) is lower for phthalic acid than isophthalic acid. (b)
Explain why the pKa for loss of the second proton (pKa2) is higher for
phthalic acid than isophthalic acid.
OH
OH
phthalic acid
pKa1 = 2.9
pKa2 = 5.4
HO
isophthalic acid
pkat = 3.7
PK a2 = 4.6
pKa2
Draw out the single
anions (one
deprotonation) and bear
in mind that there is free
rotation
about C-C single bonds.
OH Look for stabilization
based on the
conformations possible
from
Such rotation.
Chapter 22 Solutions
Organic Chemistry Study Guide and Solutions
Ch. 22 - Prob. 22.1PCh. 22 - Prob. 22.2PCh. 22 - Prob. 22.3PCh. 22 - Prob. 22.4PCh. 22 - Prob. 22.5PCh. 22 - Prob. 22.6PCh. 22 - Prob. 22.7PCh. 22 - Prob. 22.8PCh. 22 - Prob. 22.9PCh. 22 - Prob. 22.10P
Ch. 22 - Prob. 22.11PCh. 22 - Prob. 22.12PCh. 22 - Prob. 22.13PCh. 22 - Prob. 22.14PCh. 22 - Prob. 22.15PCh. 22 - Prob. 22.16PCh. 22 - Prob. 22.17PCh. 22 - Prob. 22.18PCh. 22 - Prob. 22.19PCh. 22 - Prob. 22.20PCh. 22 - Prob. 22.21PCh. 22 - Prob. 22.22PCh. 22 - Prob. 22.23PCh. 22 - Prob. 22.24PCh. 22 - Prob. 22.25PCh. 22 - Prob. 22.26PCh. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Prob. 22.30PCh. 22 - Prob. 22.31PCh. 22 - Prob. 22.32PCh. 22 - Prob. 22.33PCh. 22 - Prob. 22.34PCh. 22 - Prob. 22.35PCh. 22 - Prob. 22.36PCh. 22 - Prob. 22.37PCh. 22 - Prob. 22.38PCh. 22 - Prob. 22.39PCh. 22 - Prob. 22.40PCh. 22 - Prob. 22.41PCh. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - Prob. 22.44PCh. 22 - Prob. 22.45PCh. 22 - Prob. 22.46PCh. 22 - Prob. 22.47PCh. 22 - Prob. 22.48PCh. 22 - Prob. 22.49PCh. 22 - Prob. 22.50PCh. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Prob. 22.54PCh. 22 - Prob. 22.55APCh. 22 - Prob. 22.56APCh. 22 - Prob. 22.57APCh. 22 - Prob. 22.58APCh. 22 - Prob. 22.59APCh. 22 - Prob. 22.60APCh. 22 - Prob. 22.61APCh. 22 - Prob. 22.62APCh. 22 - Prob. 22.63APCh. 22 - Prob. 22.64APCh. 22 - Prob. 22.65APCh. 22 - Prob. 22.66APCh. 22 - Prob. 22.67APCh. 22 - Prob. 22.68APCh. 22 - Prob. 22.69APCh. 22 - Prob. 22.70APCh. 22 - Prob. 22.71APCh. 22 - Prob. 22.72APCh. 22 - Prob. 22.73APCh. 22 - Prob. 22.74APCh. 22 - Prob. 22.75APCh. 22 - Prob. 22.76APCh. 22 - Prob. 22.77APCh. 22 - Prob. 22.78APCh. 22 - Prob. 22.79APCh. 22 - Prob. 22.80APCh. 22 - Prob. 22.81APCh. 22 - Prob. 22.82APCh. 22 - Prob. 22.83APCh. 22 - Prob. 22.84APCh. 22 - Prob. 22.85APCh. 22 - Prob. 22.86APCh. 22 - Prob. 22.87APCh. 22 - Prob. 22.88APCh. 22 - Prob. 22.89APCh. 22 - Prob. 22.90APCh. 22 - Prob. 22.91APCh. 22 - Prob. 22.92APCh. 22 - Prob. 22.93APCh. 22 - Prob. 22.94APCh. 22 - Prob. 22.95APCh. 22 - Prob. 22.96APCh. 22 - Prob. 22.97APCh. 22 - Prob. 22.98AP
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
- Using the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.arrow_forwardPyridine forms a stronger Lewis acid-base complex with SO3 than SO2. However, pyridine forms a weaker complex with SF6 than with SF4. Explain the difference.arrow_forwardFor each of the following pairs, indicate which of the two is the stronger base: (a) F─ or I─ (b) CH3-NH2 or CH3-NH3+arrow_forward
- Provide an explanation without using the pka values : Why is phenol stronger acid than butanoic acid?arrow_forwardAniline (conjugate acid pKa 4.63) is a considerably stronger base than diphenylamine (pKa 0.79). Account for these marked differences.arrow_forwardThe following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Of these three anticonvulsants, one is considerably more acidic than the other two. Which is the most acidic compound? Estimate its pKa and account for its acidity. How does its acidity compare with that of phenol? with that of acetic acid?arrow_forward
- In each of the following reactions, two possible organic products can be formed. Draw both organic products in each case and then circle the one formed in greatest quantity in each case. HC (a) 1) NaH, 2) acid (b) CH,CH,OH (c) CH,CH,OH NH2 (d) Oarrow_forwardWrite equations for the reactions of the following Bronsted bases with water: (a) NH3 (b) TeO3 2- (c) CH3CH2CO2arrow_forwardUsing molecular structures, what will happen in the following situations: 1) Benzoic acid is dissolved in diethyl ether and then 1 M HCl (aq) is added: 2) Ethyl 4-aminobenzoate is dissolved in dichloromethane and then 1 M NaOH (aq) is addedarrow_forward
- 19-33 Rank the amines in each set in order of increasing basicity. (b) sbims ne (a) NH2 NH2 N. H (c) H (d) NH2 NH2 NH2 H3C H2 (е) NH2 CH,NH, CONH,arrow_forwardPhthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base. (a) Explain why the pKa for loss of the first proton (pKa1) is lower for phthalic acid than isophthalic acid. (b) Explain why the pKa for loss of the second proton (pKa2) is higher for phthalic acid than isophthalic acid.arrow_forwardWhich Nitrogen containing compound is the most basic? N (A) H-C N (B) NH4 (C) (D)arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning