Concept explainers
Interpretation:
p-Nitrophenol and 2,6-dimethyl-4-nitrophenol both have a pKa of 7.15 but 3,5-dimethyl-4-nitrophenol has pKa of 8.25. Why 3,5-dimethyl-4-nitrophenol is much less acidic is to be explained.
Concept introduction:
Resonance delocalization occurs only when the molecule is planar facilitating the overlapping of the orbitals. If the substituent groups present prevent co-planarity of the molecule then resonance is not possible.
pKa = -log Ka, where Ka is the dissociation constant of the acid. Thus a stronger acid has a low pKa value.
To explain:
Why 3,5-dimethyl-4-nitrophenol is much less acidic with pKa of 8.25 when compared to p-nitrophenol and 2,6-dimethyl-4-nitrophenol both of which have a pKa of 7.15.

Trending nowThis is a popular solution!

Chapter 17 Solutions
EBK ORGANIC CHEMISTRY
- Assign the functional group bands on the IR spectra.arrow_forwardFind the pH of a 0.120 M solution of HNO2. Find the pH ignoring activity effects (i.e., the normal way). Find the pH in a solution of 0.050 M NaCl, including activityarrow_forwardPlease help me answer these three questions. Required info should be in data table.arrow_forward
- Draw the major organic substitution product or products for (2R,3S)-2-bromo-3-methylpentane reacting with the given nucleophile. Clearly drawn the stereochemistry, including a wedged bond, a dashed bond and two in-plane bonds at each stereogenic center. Omit any byproducts. Bri CH3CH2O- (conc.) Draw the major organic product or products.arrow_forwardTartaric acid (C4H6O6) is a diprotic weak acid. A sample of 875 mg tartaric acid are dissolved in 100 mL water and titrated with 0.994 M NaOH. How many mL of NaOH are needed to reach the first equivalence point? How many mL of NaOH are needed to reach the second equivalence point?arrow_forwardIncluding activity, calculate the solubility of Pb(IO3)2 in a matrix of 0.020 M Mg(NO3)2.arrow_forward
- Order the following series of compounds from highest to lowest reactivity to electrophilic aromatic substitution, explaining your answer: 2-nitrophenol, p-Toluidine, N-(4-methylphenyl)acetamide, 4-methylbenzonitrile, 4-(trifluoromethyl)benzonitrile.arrow_forwardOrdene la siguiente serie de compuestos de mayor a menor reactividad a la sustitución aromática electrofílica, explicando su respuesta: ácido bencenosulfónico, fluorobenceno, etilbenceno, clorobenceno, terc-butilbenceno, acetofenona.arrow_forwardCan I please get all final concentrations please!arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher: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



