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Concept explainers
Interpretation:
A pair of chain propagation steps for the radical bromination of propane to give 1-bromopropane has to be written and
Concept introduction:
Halogenation of
Radical chain reaction:
Initiation reaction:
Chain propagation:
Chain termination:
It is a change in enthalpy of a homolysis reaction at absolute zero where a molecule is broken down into two free radicals.
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Chapter 8 Solutions
Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- 2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.arrow_forwardfluorination of alkanes is highly exothermic. Per Hammond’s postulate, assume that the transition state for radical fluorination is almost identical to the starting material. Assuming this fact, estimate the fraction of each monofluoro product formed in the fluorination of 2-methylbutane.arrow_forwardThe compound below is treated with chlorine in the presence of light. H3C 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
- The chlorination of ethane produces many by-products. One by-product that forms in small amounts is 2-chlorobutane. Suggest a mechanism for the formation of 2-chlorobutane from the radical chlorination of ethane. (NOTES: intermediates can only have one radical, 2-chlorobutane should be the product of your termination step, any intermediate radical formed during the propagation phase can be used in the termination step)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_forwardFree‑radical halogenation can occur with chlorine and a source of direct UV radiation or sunlight. Chlorination of 2,4‑dimethylpentane via radical halogenation leads to the formation of all three of the products shown. Estimate the relative percentages of each product that will be formed using this means of halogenation. Presume that 1 equivalent of chlorine is used.arrow_forward
- When HBr adds to (CH3)2C = CH2 under radical conditions, two radicals are possible products in the first step of chain propagation. Draw the structure of both radicals and indicate which one is formed. Then draw the preferred product from HBr addition under radical conditions.arrow_forwardThe compound below is treated with chlorine in the presence of light. CH3 CH3 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. Sn [F ?arrow_forwardWhich of the following is a chain propagation step in the free radical chlorination of methane? · CH3 + Cl · → CH3CI Cl2 2 Cl · CH4 + Cl HCl + · CH3 CH3 + CH4 CH4 + ·CH3arrow_forward
- A 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_forwardUsing the table of average bond dissociation enthalpies at 25°C, determine which of the following reactions are energetically favorable at room temperature. Assume that ▲S = 0. Q.CH2=CH2 + CH4 --> CH3CH2CH3arrow_forwardIn the second paragraph you should explain why 2-chloro-2-methylpropane reacts with water via the SN1 mechanism instead of the SN2 mechanism, and then write the steps in the mechanism for this reaction. Then write the balanced equation for the reaction between 2-methyl-2-chloropropane and water. One of the products of this reaction is HCl. The rate at which HCl is produced is equal to the rate at which 2-chloro-2-methylpropane is consumed. In this experiment, the HCI will be neutralized by incremental addition of a sodium hydroxide solution. Write the balanced equation for the reaction between NaOH and HCI.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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