Concept explainers
(a)
Interpretation: The stable carbonyl compound,
Concept introduction: Electron withdrawing groups pulls electron density towards itself, and thus destabilizes the benzene ring, whereas electron releasing groups push electron density away from it, that is towards benzene ring, and thus stabilizes the benzene ring more.
(b)
Interpretation: The compound that forms higher percentage of hydrate at equilibrium is to be identefied.
Concept introduction:
(c)
Interpretation: The compound that exhibits carbonyl absorption at higher wavenumber in its
Concept introduction: Electron releasing groups decreases the bond order of the
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ORGANIC CHEMISTRY W/CONNECT PKG
- Match the ff reagents: a. Br₂ in CH₂Cl₂ b.CrO₃ , H₂SO₄, acetone c. concentrated HCl with ZnCl₂ d. aqueous FeCl₃ e. aqueous NaHCO₃ f. ammoniacal AgNO₃ 1. 4-bromophenol from benzene 2. hexane from 1-hexene 3. 1-hexanol from hexanal 4. hexane from hexanoic acid 5. 2-hexanol from 2-methyl-2-hexanol 6. 1-hexene from 1-hexynearrow_forward1. a. 4-methoxybenzoic acid is less or more polar than 4-methoxyacetophenone? explain why (WITHOUT DRAWINGS) b. 3′-chloro-4′-methoxyacetophenone is less or more polar than 4-methoxyacetophenone? explain why (WITHOUT DRAWINGS)arrow_forward1. Why does H2 not give an IR spectrum? 2. Explain why primary amines and unsubstituted amides have two NH stretching absorptions. 3. Why do anhydrides show two carbonyl peaks? 4. HCl is known to give addition reactions to carbon-carbon double bonds. Why is this behavior not observed in this reaction? 5. Predict the structure of the product expected from addition of molecular bromine to maleic acid.arrow_forward
- 1. a. 4-methoxybenzoic acid is less or more polar than 4-methoxyacetophenone? explain why (WITHOUT DRAWINGS) b. 3′-chloro-4′-methoxyacetophenone is less or more polar than 4-methoxyacetophenone? explain why (WITHOUT DRAWINGS) 2. a. 4-methoxybenzoic acid has a higher melting point than 4-methoxyacetophenone. explain why? (WITHOUT DRAWINGS) b. 3′-chloro-4′-methoxyacetophenone has a higher melting point than 4-methoxyacetophenone. explain why? (WITHOUT DRAWINGS)arrow_forwardExplain each statement. a. The pKa of p-nitrophenol is lower than the pKa of phenol (7.2 vs. 10). b. The pKa of p-nitrophenol is lower than the pKa of m-nitrophenol (7.2 vs. 8.3).arrow_forwardIdentify products A and B from the given 1H NMR data.a. Treatment of CH2 = CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?b. Treatment of acetone [(CH3)2C = O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forward
- Identify products A and B from the given 1H NMR data. a.Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A? b.Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forwardWhich of the following set of reagents will make cyclobutamine from bromocyclobutane? a NaN3 / ethanol and LiAlH4 in ether solution b NH3 and NaBH4 in ethanol solution c NaCN and LiAlH4 in ether solution d NH3 and H2 /Pdarrow_forwardSearch a reaction scheme for each reaction and draw the step-by-step mechanism using curved arrows for the following reactions. Explain how the IR spectrum (IR peaks of the functional groups) of the product would differ from that of the reactant in each reaction Grignard reaction Reduction of aldehydes or ketones Acetal or Ketal formation Wittig reactionarrow_forward
- What compound is formed when a dilute solution of cyclohexanone is shaken with NaOD in D2O for several hours?arrow_forwardDrawing a Dehydration Reaction with a Rearrangement Show how the dehydration of alcohol X forms alkene Y using a 1,2-hydride shift.arrow_forwardUse the four compounds shown below to answer the following questions: a. Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid?b. Why is o-fluorobenzoic acid the weakest of the ortho-halo-substituted benzoic acids?c. Why do o-chlorobenzoic acid and o-bromobenzoic acid have similar pKa values?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningMacroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole