Concept explainers
(a)
Interpretation:
The compound has to be matched with appropriate
Concept introduction:
Resonance effect:
Organic compound contains double bonds, it will involve in the overlap of p-orbitals on the two adjacent carbon atoms.
Inductive effect:
The electronic effect arises due to the polarisation of σ bonds within a molecule and it is due to an electronegativity difference between the atoms.
(b)
Interpretation:
The compound has to be matched with appropriate
Concept introduction:
Resonance effect:
Organic compound contains double bonds, it will involve in the overlap of p-orbitals on the two adjacent carbon atoms.
Inductive effect:
The electronic effect arises due to the polarisation of σ bonds within a molecule and it is due to an electronegativity difference between the atoms.
(c)
Interpretation:
The compound has to be matched with appropriate
Concept introduction:
Resonance effect:
Organic compound contains double bonds, it will involve in the overlap of p-orbitals on the two adjacent carbon atoms.
Inductive effect:
The electronic effect arises due to the polarisation of σ bonds within a molecule and it is due to an electronegativity difference between the atoms.
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Chapter 21 Solutions
Organic Chemistry
- Phenacetin, a substance formerly used in over-the-counter headache remedies, has the formula C10H13NO2. Phenacetin is neutral and does not dissolve in either acid or base. When warmed with aqueous NaOH, phenacetin yields an amine, C8H11NO, whose 1H NMR spectrum is shown. When heated with HI, the amine is cleaved to an aminophenol, C6H7NO. What is the structure of phenacetin, and what are the structures of the amine and the aminophenol?arrow_forwardPhenacetin is an analgesic compound having molecular formula C10H13NO2. Once a common component in over-thecounter pain relievers such as APC (aspirin, phenacetin, caffeine), phenacetin is no longer used because of its liver toxicity. Deduce the structure of phenacetin from its 1H NMR and IR spectra.arrow_forwardWhat is the concentration of Enol and Keto from this NMR Spectra?arrow_forward
- How would you distinguish between methyl benzoate and phenylacetic acid using 1H NMR spectroscopy?arrow_forwardMatch each compound with its appropriate pKa value. Q.) 4-Nitrobenzoic acid, 4-nitrophenol, 4-nitrophenylacetic acid pKa 5 7.15, 3.85, and 3.41arrow_forwardA naturally occurring amino acid such as alanine has a group that is a carboxylic acid and a group that is a protonated amine. The pKa values of the two groups are shown.(a). If the pKa value of a carboxylic acid such as acetic acid is about 5, then why is the pKa value of the carboxylic acid group of alanine so much lower? (b). Draw the structure of alanine in a solution at pH = 0. (c). Draw the structure of alanine in a solution at physiological pH (pH 7.4).(d). Draw the structure of alanine in a solution at pH = 12. (e). Is there a pH at which alanine is uncharged (that is, neither group has a charge)? (f) At what pH does alanine have no net charge (that is, the amount of negative charge is the same as the amount of positive charge)?arrow_forward
- Draw a mechanism of a reversible reaction of acetophenone and strong acid (H-A) to form a protonated acetophenone and a weak base. Draw all the electron pairs of the molecules and the arrows. Predict 1H NMR spectra of acetophenone and the protonated acetophenone.arrow_forwardSuggest an explanation for the following observation. The carbonyl group of methyl salicylate absorbs at a significantly lower wavenumber than the carbonyl group of methyl benzoate.arrow_forwardWhen but-2-enal is treated with 3-phenylpropenal in the presence of a strong base, a compound is formed whose formula is C13H12O. In its 1H NMR spectrum, one signal has a chemical shift around 10 ppm, several overlapping signals have chemical shifts between 7 and 9 ppm, and several other overlapping signals have chemical shifts between 5 and 6 ppm. Integration of those sets of signals gives a 1∶5∶6 ratio.(a) What is the structure of the product?(b) Draw a complete, detailed mechanism that accounts for the formation of the product.arrow_forward
- Explain why the pKa of compound A is lower than the pKa's of bothcompounds B and C.arrow_forwardAnalyse the high resolution proton NMR spectrum of a compound with a molecular formula of C8H16O2 and and write its name. Options: A. 2-ethylhexanoic acid B. 1,4-cyclohexanedimethanol C. ethyl hexanoate D. butyl butyrate E. ethyl 2,2-dimethylpropanoatearrow_forwardCarbon NMR Spectrum A has peaks at delta 71, 40, 19, and 12. Spectrum B has peaks at delta 72, 38, 31, 29, 22, 12, and 10. Which spectrum corresponds to 1-heptanol, and which corresponds to 4-heptanol. Explain your answer using structures.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning