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
- Ketones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+=74 in the mass spectrum?arrow_forwardAnethole, C10H12O, a major constituent of the oil of anise, has the 1H NMR spectrum shown. On oxidation with Na2Cr2O7, anethole yields p-methoxybenzoic acid. What is the structure of anethole? Assign all peaks in the NMR spectrum, and account for the observed splitting patterns.arrow_forward7. Which has the higher boiling point, 1-butanol or 1-butanamine? 8. Circle the stronger base in the pair below, and briefly explain your choice. or (CH3CH2)2NH 9. How might one distinguish a sample of trimethylamine from a sample of n-propylamine using IR spectroscopy? ¹H NMR spectroscopy? ¹³C NMR spectroscopy?arrow_forward
- Show the effect of conjugation on the carbonyl absorption in an IR spectrum ?arrow_forwardFor the product, triphenylmethanol, what peaks should we see in 1) 1H NMR 2) 13C NMR, and 3) IR spectra?arrow_forwardIn 1H and 13C NMR spectra, how many signals does the unsaturated ketone (CH3)2CHCH2C (O)CH=CH2 have? Choices: 6H-6C, 5H-6C, 5H-7C, 6H-7Carrow_forward
- Compound A reacts with 1 equivalent of methyl Grignard reagent to give B as the product. IR of B has a strong absorption at 1680 cm. What is the structure of B? Propose a stepwise mechanism to B. A MeMgBrarrow_forwardPredicting the Relative Position of Carbonyl Absorptions Rank compounds A, B, and C in order of increasing frequency of the carbonyl absorption in their IR spectra.arrow_forward11 8. When benzene is treated with Reagent(s) A followed by Reagent(s) B, Compound P (CaHCIO) is the major product. If the order of reagents is reversed, Compound Q (also CaHCIO) is formed instead (see the scheme below). Both P and Q have a strong IR absorption around 1685 cm, H and "C NMR spectra of P and Q are shown below. Draw the structures of P and Q and list the Reagents A and B. Benzene 10 1. A 2. B 9 Compound P ¹H NMR Compound Q ¹H NMR 2:2 السر 2:1:1 ppm 5 ppm : 3 3 Benzene DEPT-90 DEPT-135 0 DEPT-90 200 180 200 DEPT-135 1. B 2. A 180 160 160 140 12 140 120 120 100 ppm Compound P 13C NMR 2 peaks 60 BO Compound Q 13C NMR 100 ppm 80 60 40 -8 20 20arrow_forward
- Explain 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_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_forwardCompound H (C,H,O,) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens' solution. Following is its 'H-NMR spectrum. Deduce the structure of compound H. Compound H 2H IH IH IH 7 5 Chemical shift (8) 0 ppm 10 9. 8. 3. 2.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning