Concept explainers
(a)
To determine: The initiation and propagation steps that account for the given reaction.
Interpretation: The initiation and propagation steps that account for the given reaction is to predicted.
Concept introduction: The
(b)
To determine: The value of
Interpretation: The value of
Concept introduction: The chemical reaction which proceeds through the formation of radicals is known as chain reaction. It involves three steps, initiation, propagation and termination. The initiation step occurs in the presence of light. The quantum yield of chain reactions is very high.
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ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
- The compound below is treated with chlorine in the presence of light. H₂C CH3 H₂C CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. Undoarrow_forwardAs we will learn in Section 15.12, many antioxidants-compounds that prevent unwanted radical oxidation reactions from occurring-are phenols, compounds that contain an OH group bonded directly to a benzene ring. a. Explain why homolysis of the O-H bond in phenol requires considerably less energy than homolysis of the O-H bond in ethanol (362 kJ/mol vs. 438 kJ/mol). b. Why is the C-O bond in phenol shorter than the C-O bond in ethanol? -O-H CH,CH2-0-H phenol ethanolarrow_forwardAlcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forward
- Following is a balanced equation for the allylic bromination of propene. CH2==CHCH3 + Br2 h CH2==CHCH2Br + HBr (a) Calculate the heat of reaction, H 0, for this conversion. (b) Propose a pair of chain propagation steps and show that they add up to the observed stoichiometry. (c) Calculate the H 0 for each chain propagation step and show that they add up to the observed H 0 for the overall reaction.arrow_forwardThe compound below is treated with chlorine in the presence of light. CH3 CH3CHCH₂CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. n [ ]# ?arrow_forwardMost supersonic planes produce exhaust of hot gases containing many compounds, including nitric oxide (NO). Nitric oxide is a radical that is believed to play a role in ozone depletion. Propose propagation steps that show how nitric oxide can destroy ozone in a chain process.arrow_forward
- 1. Predict the product(s) and propose a mechanism of the following nucleophilic substitution reaction. Remember that a mechanism should contain arrows to show movement of electrons, all intermediates and appropriate formal charges. Br + H₂O →arrow_forwardThe compound below is treated with chlorine in the presence of light. CH3CH2CH2CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond.arrow_forwardThe compound below is treated with chlorine in the presence of light. H₂C CH3 H3C CH₂CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms.arrow_forward
- Please answer the two items. The following compounds are major products of an elimination reaction with an alkyl halide. Determine the structure of the alkyl halide. Write the overall reaction mechanism. Tip: Remember your Markovnikov’s rule. Follow the progress of the reaction and look at the stability of the intermediate products and transition states to determine the minor and major products.arrow_forwardAlcohols are acidic in nature. Therefore, a strong base can abstract the acidic hydrogen atom of the alcohol in a process known as deprotonation. The alcohol forms an alkoxide ion by losing the proton attached to the oxygen atom of the hydroxyl ( -OH) group. The alkoxide formed can act as a base or a nucleophile depending on the substrate and reaction conditions. However, not all bases can abstract the acidic proton of alcohols and not all alcohols easily lose the proton. Deprotonation depends on the strength of the base and the acidity of the alcohol. Strong bases, such as NaNH2, can easily abstract a proton from almost all alcohols. Likewise, more acidic alcohols lose a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ► View Available Hint(s) CH3CH,OH + NH3 →CH,CH,O-NH CH3 CH3 H3C-C-H+NH3 → H3 C-C-H OH O-NH CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3 CHC12 Cl₂…arrow_forwardA benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning