(a)
Interpretation:
The mechanism for the free-radical addition of hydrogen bromide to cyclohexene initiated by
Concept introduction:
The general steps followed by free-radical addition reaction are stated below:
• First step is initiation that involves formation of radical.
• Second step is propagation.
• Third step is the termination that involves the formation of stable bond
(b)
Interpretation:
The three radical recombination products that might be formed in small amounts in the termination phase of the reaction are to be suggested.
Concept introduction:
The general steps followed by free-radical addition reaction are stated below:
• First step is initiation that involves formation of radical.
• Second step is propagation.
• Third step is the termination that involves the formation of stable bond
Want to see the full answer?
Check out a sample textbook solutionChapter 5 Solutions
Organic Chemistry
- Furan undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient.For example, furan reacts with bromine to give 2-bromofuran.(a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms ofeach sigma complex, and compare their stabilities.(b) Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.O Br O123furan 2-bromofuranarrow_forwardAlkyl halides can be reduced to alkanes by a radical reaction with tributyltin hydride, (C4H9)3SnH, in the presence of light (hv). Propose a radical chain mechanism by which the reaction might occur. The initiation step is the light-induced homolytic cleavage of the Sn-H bond to yield a tributyltin radical.arrow_forwardFollowing is an equation for hydroperoxidation of cumene. light + O2 for HOO- Cumene Cumene hydroperoxide Propose a radical chain mechanism for this reaction. Assume that initiation is by an unspecified radical, R.arrow_forward
- (3) HI does not undergo free radical addition with 1-butene, even in the presence of a peroxide. Please provide an explanation by analyzing the propagation steps if the same radical reaction occurred with HI. Besides the bond dissociation enthalpies in the appendix, the following approximate bond dissociate enthalpies might be useful to you: ~310 kJ/mol The component of C=C CH3CH₂CH₂CH₂-Br CH3CH₂CH₂CH2-I -290 kJ/mol (C-Br bond) ~235 kJ/mol (C-I bond)arrow_forward• H2O Based on the reaction above, (a) Outline the reaction mechanism. (b) Sketch the energy diagram. (c) Give the rate equation. (d) Explain what happens to the reaction rate if: The leaving group is changed to I. (0) (a) The solvent is changed to DMF. The alkyl halide is changed to (v) The concentration of the solvent is increased by five-fold answer with proper justification and with good explanationarrow_forwardPyrrole is a π-excessive heteroaromatic molecule. (i) Explain, using resonance structures, the term π-excessive heteroaromatic. (ii) Name the reactions typically undergone by aromatic molecules, and discuss how readily these occur for pyrrole. (iii) Pyrrole undergoes polymerisation under acidic conditions. Draw a reaction mechanism to explain this observation.arrow_forward
- The rate law for addition of Br2 to an alkene is first orderin Br2 and first order in the alkene. Does this informationsuggest that the mechanism of addition of Br2 to analkene proceeds in the same manner as for addition of HBr?Explain.arrow_forwardAnswer the following questions regarding the nucleophilic substitution reaction shown below: CH3CH2CH2-Br + I- ------> CH3CH2CH2I + Br- (a) Write the rate law for this reaction assuming that it is a one step reaction that is first order in each of the reactants. (b) Holding the concentration of the iodide ion constant, what change would be observed in the rate if the concentration of the n- propyl bromide was tripled? (b) Assume that this is an exothermic reaction, draw the energy profile and identify the location of the transition state. (c) Draw the transition state for this reaction. (d) What change is observed for the entropy of the system during this reaction? (e) Show the likely mechanism of this reaction using the proper curved arrowsarrow_forwardSuggest mechanisms for the following reactions, both of which involve radical intermediates: (b) (c) Br. MeO MeO CO₂Et N-NO Bu3SnH, AIBN heat hv HO `N MeO MeO NH CO₂Etarrow_forward
- With regards to this, I have been reading journals about activated carbon that is being modified. Now, the activated carbon is modified through acid treatment, and sulfuric acid is added to it. The result was, that there is a presence of SO3-, C=O=C, and C=O on the modified activated carbon. They concluded that the process of sulfonation on the activated carbon treated with sulfuric acid took place. Can you explain the chemistry/mechanism/reaction that happened? Explain in detail and clearly. Thank you so much!arrow_forwardPlease give the main substitution product for each of the following reactions, and indicate the dominant mechanism: (a) 1-bromopropane + NaOCH3 → (b) 3-bromo-3-methylpentane + NaOC2H5 →arrow_forward(i) Name, draw and describe the organic product of the reaction between 2-methylbut-1-ene and H2O in the presence of H2SO4 and provide a clear rationale as to why this is the major product of the reaction. (ii) The elimination reaction between 2-bromobutane and NaOCH2CH3 gives two organic products. Draw a mechanism for the reaction which produces the major organic elimination product and provide a rationale as to why that is the major product.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning