(a)
Interpretation:
To explain the following result obtain from theHammett equation.
Concept introduction:
Hammett reaction constant (
The negative value of the
(b)
Interpretation:
To explain the following result obtain from theHammett equation.
Concept introduction:
Hammett reaction constant (
The negative value of the
(c)
Interpretation:
To explain the following result obtain from theHammett equation.
Concept introduction: Hammett reaction constant (
The negative value of the
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Chapter 15 Solutions
ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
- When the three benzaldehydes shown below were exposed to HCN under identical conditions it was found that the equilibrium constants, K, for the three cyanohydrin formation reactions were different. Based on principles that govern equilibrium processes for reversible carbonyl addition reactions, place the K values for the three reactions in ascending order (smallest to largest). Briefly justify your answer. (Hint: Recall that electron deficient carbonyls tend to react faster with nucleophiles and have larger equilibrium constants for the addition reaction.) H X O + HCN pH ~ 9-10 X = H, NO₂, OCH 3 OH H+CN Xarrow_forwardFill the blank space. Compounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and ---------. The correct name (or abbreviation) of an example compound containing a phenol group with antioxidant properties is: ---------.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forward
- Explain why a carbonyl absorption shifts to lower frequency in an α,β-unsaturated carbonyl compound—a compound having a carbonyl group bonded directly to a carbon–carbon double bond. For example, the carbonyl absorption occurs at 1720 cm−1 for cyclohexanone, and at 1685 cm−1 for cyclohex-2-enone.arrow_forwardCompounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and The correct name (or abbreviation) of an example compound (discussed in the lecture videos) containing a phenol group with antioxidant properties is:arrow_forwardFuran undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient.For example, furan reacts with bromine to give 2-bromofuran. Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.arrow_forward
- *20. The two isomeric compounds with the formula C10H14 have NMR spectra shown below. Make no attempt to interpret the aromatic proton area between 7.1 and 7.3 ppm except to determine the number of protons attached to the aromatic ring. Draw the structures of the isomers. C1,H14 5.10 7.5 7.0 1.10 2.15 3.04 2.94 4.0 3.0 2.0 1.0 (а) C1,H14 5.10 7.5 7.0 2.14 2.06 2.06 2.98 4.0 3.5 3.0 2.5 2.0 1.5 1.0 (b)arrow_forwardFor following substituted benzenes: [1] C6H5Br; [2] C6H5CN; [3] C6H5OCOCH3: Does the substituent activate or deactivate the benzene ring inelectrophilic aromatic substitution?arrow_forwardA solution of acetone [(CH3)2C=O] in ethanol (CH3CH2OH) in the presence of a trace of acid was allowed to stand for several days, and a new compound of molecular formula C7H16O2 was formed. The IR spectrum showed only one major peak in the functional group region around 3000 cm−1, and the 1H NMR spectrum is given here. What is the structure of the product?arrow_forward
- The reaction of 1-bromopropane and sodium hydroxide in ethanol occurs by an SN2mechanism. What happens to the rate of this reaction under the following conditions?(a) The concentration of NaOH is doubled.(b) The concentrations of both NaOH and 1-bromopropane are doubled.(c) The volume of the solution in which the reaction is carried out is doubled.arrow_forwardAromatic heterocyclic chemistry: State whether the following drugs are aromatic heterocycles and if they follow the 4 aromaticity rules (unsaturation, (4n + 2)pi electrons, cyclic and flat/planar), NAME ANY HETEROCYCLES. Draw the structure of the core of any aromatic heterocycles in the drug. Riociguat, Imatinib, Clopidogrel, Glatiramer acetate, Axitinibarrow_forwardCompounds A and B are isomers having the molecular formula C4H8O3. Identify A and B on the basis of their 1H NMR spectra.Compound A: δ 1.3 (3H, triplet); 3.6 (2H, quartet); 4.1 (2H, singlet); 11.1 (1H, broad singlet)Compound B: δ 2.6 (2H, triplet); 3.4 (3H, singlet); 3.7 (2H triplet); 11.3 (1H, broad singlet)arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning