Concept explainers
(a)
Interpretation:
The reason as to why the unpaired electron in the allyl radical is delocalized over
Concept introduction:
Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure.
(b)
Interpretation:
The reason as to why the unpaired electron in the allyl radical is delocalized over
Concept introduction:
The molecular orbital is a combination of two atomic orbitals. It is used to represent the regions in a molecule where the electron is likely to be present in an orbital. It represents the wave-like nature of an electron in a molecule.
Want to see the full answer?
Check out a sample textbook solutionChapter 28 Solutions
Organic Chemistry
- Following is a balanced equation for bromination of toluene. (a) Using the values for bond dissociation enthalpies given in Appendix 3, calculate H0 for this reaction. (b) Propose a pair of chain propagation steps and show that they add up to the observed reaction. (c) Calculate H0 for each chain propagation step. (d) Which propagation step is rate-determining?arrow_forwardWrite a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. A. Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. B. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. C.Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Cl- will act as the base in this reaction.arrow_forwardThe C‚N triple bond in acetonitrile has a dipole moment of about 3.6 D and a bond length of about 1.16 Å. Calculate the amount of charge separation in this bond. How important is the charge-separated resonance form in the structure of acetonitrile?arrow_forward
- What is the function of CH2Cl2 in the bromination reactions? Why can it fulfil this rolearrow_forwardIn cells, vitamin C exists largely as its conjugate base X. X is an antioxidant because radicals formed in oxidation processes abstract the labeled H atom, forming a new radical that halts oxidation. Draw the structure of the radical formed by H abstraction, and explain why this H atom is most easily removed.arrow_forwardExplain the substituent effect on properties of selected molecules such as resonance stability, acidity, acidic properties, basic properties and carbocation stabilityarrow_forward
- You are required to synthesize 2-bromopentane from the reaction between an alkene with HBr. Which alkene, 1-pentene or 2-pentene, should you react with HBr in order to get 2-bromopentane? Give an explanation.arrow_forwardIllustrate how diazomethane and ozone can both behave as 1,3-dipoles. Indicate, by drawing their resonance forms, how they can do so and draw the products of their reaction with styrenearrow_forwardHaving one mole of carbon suboxide (C2O3) means that you havearrow_forward
- Diels–Alder reaction of a monosubstituted diene (such as CH2=CH– CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant, and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.arrow_forwardAccount for the fact that among the chlorinated derivatives of methane, chloromethane has the largest dipole moment and tetrachloromethane has the smallest dipole moment.arrow_forwardDiels—Alder reaction of a monosubstituted diene (such as CH2 = CH – CH = CHOCH3) with a monosubstituted dienophile (such as CH2 = CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning