
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.

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Chapter 17 Solutions
Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)
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- Identify the mechanism through which the following reaction will proceed and draw the major product. Part 1 of 2 Br KOH EtOH Through which mechanism will the reaction proceed? Select the single best answer. E1 E2 neither Part: 1/2 Part 2 of 2 Draw the major product formed as a result of the reaction. Click and drag to start drawing a structure. Xarrow_forwardWhat is single-point calibration? Provide an example.arrow_forwardDraw the major product formed via an E1 pathway.arrow_forward
- Part 9 of 9 Consider the products for the reaction. Identify the major and minor products. HO Cl The E stereoisomer is the major product and the Z stereoisomer is the minor product ▼ S major product minor productarrow_forwardConsider the reactants below. Answer the following questions about the reaction mechanism and products. HO Clarrow_forwardjulietteyep@gmail.com X YSCU Grades for Juliette L Turner: Orc X 199 A ALEKS - Juliette Turner - Modul X A ALEKS - Juliette Turner - Modul x G butane newman projection - Gox + www-awa.aleks.com/alekscgi/x/Isl.exe/10_u-IgNslkr7j8P3jH-IBxzaplnN4HsoQggFsejpgqKoyrQrB2dKVAN-BcZvcye0LYa6eXZ8d4vVr8Nc1GZqko5mtw-d1MkNcNzzwZsLf2Tu9_V817y?10Bw7QYjlb il Scribbr citation APA SCU email Student Portal | Main Ryker-Learning WCU-PHARM D MySCU YSCU Canvas- SCU Module 4: Homework (Ch 9-10) Question 28 of 30 (1 point) | Question Attempt: 1 of Unlimited H₂SO heat OH The mechanism of this reaction involves two carbocation intermediates, A and B. Part 1 of 2 KHSO 4 rearrangement A heat B H₂O 2 OH Draw the structure of A. Check Search #t m Save For Later Juliet Submit Assignm 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

