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Write a stepwise mechanism for each of the following reactions. Explain why a more stable
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Chapter 11 Solutions
Organic Chemistry
- Draw the structure for an alkene that gives the following reaction product. CH3 -CHCH₂CH3 ? CH₂l2, Zn/Cuarrow_forwardCCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*arrow_forwardNAME and DRAW the STRUCTURE of ALL the alkenes which could undergo catalytic hydrogenation at 900°C to form methylcyclopentane. Circle the alkene with the HIGHEST stability and X the alkene with the HIGHEST heat of hydrogenation. Give reasons for your choice.arrow_forward
- Assuming nucleophilic substitution reactions will occur, which will produce racemic products? CH;CH,CH(CI)CH3 + NANH, CH3CH2CH(CI) CH3 + CH3S¯Na* CH;CH,CH(CI)CH,CH3 + NH3 O CH;CH2CH(CI) CH3 + CH3OHarrow_forwardWhat reaction conditions are needed to convert (R)-2-ethyl-2-methyloxirane to (S)-2- methylbutane-1,2-diol ?arrow_forwardDraw the structure of each product from the reaction of benzene with 2-chloro-1-methylcyclohexane using AlCl 3 as the catalyst and Identify the major product.arrow_forward
- Explain the different products of the following two reactions by considering the mechanism by which each reaction proceeds. As part of your explanation, use the curved arrow formalism to draw a mechanism for each reaction. CH,OH CH2=CH-CH-CH, + Na*¯OCH, CH;=CH-CH-CH3 Br OCH, CH,=CH-CH-CH, + CH,OH – CH,=CH–CH–CH, + CH,CH=CHCH, Br OCH, OCH,arrow_forwardThe major product formed by addition of HBr to (CH3)2C=CH– CH=C(CH3)2 is the same at low and high temperature. Draw the structure of the major product, and explain why the kinetic and thermodynamic products are the same in this reaction.arrow_forwardC=CH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-OH HO: Hjö: C=CH c=CH Hö Hg Hgarrow_forward
- Take 1-methylcyclohexene as the alkene and treat it with the reagent.arrow_forwardIdentify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.arrow_forwardAddition of HBr to allene (CH2=C=CH2) forms 2-bromoprop-1-ene ratherthan 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed froman allylic carbocation. Considering the arrangement of orbitals in theallene reactant, explain this result.arrow_forward
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