Consider the following organic reaction, in which onehalogen replaces another in an alkyl halide:CH₃+CH₂+BrKI→CH₃+CH₂I+KBr .In acetone, this particular reaction goes to completion becauseKI is soluble in acetone but KBr is not. In the mechanism, Iapproaches the carbon oppositeto the Br . After Br⁻ has been replaced by I⁻ and precipitates as KBr, other I⁻ ions react with the ethyliodide by the same mechanism.(a) If we designate the carbon bonded to the halogen as C-1,what is the shape around C-1 and the hybridization of C-1 inethyl iodide?(b) In the transition state, one of the two lobes of the unhy-bridized 2porbital of C-1 overlaps a porbital of I, while theother lobe overlaps a porbital of Br. What is the shape aroundC-1 and the hybridization of C-1 in the transition state?(c) The deuterated reactant, CH₃CHDBr (where D is deuterium,2H), has two optical isomers because C-1 is chiral. If the reac-tion is run with one of the isomers, the ethyl iodide is notopti-cally active. Explain

Chemistry & Chemical Reactivity
9th Edition
ISBN:9781133949640
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Chapter14: Chemical Kinetics: The Rates Of Chemical Reactions
Section: Chapter Questions
Problem 86IL: The acid-catalyzed iodination of acetone CH3COCH3(aq) + I2(aq) CH3COCH2I(aq) + HI(aq) is a common...
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Consider the following organic reaction, in which onehalogen replaces another in an alkyl halide:CH₃+CH₂+BrKI→CH₃+CH₂I+KBr .In acetone, this particular reaction goes to completion becauseKI is soluble in acetone but KBr is not. In the mechanism, Iapproaches the carbon oppositeto the Br . After Br⁻ has been replaced by I⁻ and precipitates as KBr, other I⁻ ions react with the ethyliodide by the same mechanism.(a) If we designate the carbon bonded to the halogen as C-1,what is the shape around C-1 and the hybridization of C-1 inethyl iodide?(b) In the transition state, one of the two lobes of the unhy-bridized 2porbital of C-1 overlaps a porbital of I, while theother lobe overlaps a porbital of Br. What is the shape aroundC-1 and the hybridization of C-1 in the transition state?(c) The deuterated reactant, CH₃CHDBr (where D is deuterium,2H), has two optical isomers because C-1 is chiral. If the reac-tion is run with one of the isomers, the ethyl iodide is notopti-cally active. Explain

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