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Interpretation: The stereoisomer of
Concept introduction: The one-step bimolecular elimination reaction that favors the removal of a proton by a base from carbon adjacent to the leaving group that results in the formation of a carbocation is termed as
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Chapter 8 Solutions
EBK ORGANIC CHEMISTRY
- Addition of HBr to allene (CH2=C=CH2) forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.arrow_forwardConsider an E2 reaction between CH3CH2Br and KOC(CH3)3. What effect does each of the following changes have on the rate of elimination? (a) The base is changed to KOH. (b) The alkyl halide is changed to CH3CH2Cl.arrow_forwardWhy do cis-1-bromo-2-ethylcyclohexane and trans-1-bromo-2-ethylcyclohexane form different major products when they undergo an E2 reaction?arrow_forward
- There are two stereoisomers of 1-tert-butyl-4-chloro-cyclohexane. One of these isomers reacts with sodium ethoxide in an E2 reaction that is 500 times faster than the reaction of the other isomer. Identify the isomer that reacts faster and explain the difference in rate for these two isomers.arrow_forwardThe reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs due to a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain what this observation tells about the mechanism of the reaction.arrow_forwardDraw a structure for the product of nucleophilic substitution obtained on solvolysis of tert-butyl bromide in methanol, and arrange the correct mechanism for its formation. Be sure to answer all parts.arrow_forward
- Name (including E/Z stereochemistry) the five alkenes that can produce 3-bromo-3-methylhexane on reaction with HBr. Draw the skeletal structure of each molecule.arrow_forwardDraw an energy diagram for an E2 reaction: (CH3)3CBr + −OH →(CH3)2C=CH2 + H2O + Br−arrow_forwardWhich characteristics describe an E2 reaction? Choose all that apply. O Stereospecific rate = k[E-LG] Can form either the most substituted or least substituted alkene. It depends on the reagents used. Always forms the most substituted alkene (Zaitzev's rule). Unimolecular O rate = k[base][E-LG] Always forms the least substituted alkene (Hofmann's rule). O Concertedarrow_forward
- Compound A reacts with the reagents shown in the image. Write the mechanism, step by step, for the formation of product B. Note that B has the molecular formula C14 H18 O.arrow_forwardTreatment of propadiene (an allene) with hydrogen bromide produces 2-bromopropene as the major product. This suggests that the more stable carbocation intermediate is produced by the addition of a proton to Br HBr. H2C=C=CH, H3C CH2 a terminal carbon rather than to the central carbon. Propadiene 2-Bromopropene (a) Draw both carbocation intermediates that can be produced by the addition of a proton to the allene. (b) Explain the relative stabilities of those intermediates. Hint: Draw the orbital picture of the intermediates and consider whether the CH, groups in propadiene are in the same plane.arrow_forwardThe reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs via a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain in complete words what this observation tells you about the mechanism of the reaction.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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