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6.14: Solutions for Selected Problems.

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    Exercise 6.1.1:

    El = electrophile; Nu = nucleophile

    EA1pt1.png

    Exercise 6.1.2:

    EA1pt3.png

    Exercise 6.1.3:

    \[Rate = \frac{d[alkyl \: bromide]}{dt} = k[alkene][HBr] \nonumber\]

    Exercise 6.1.4:

    EA1pt4soln.png

    Exercise 6.2.1:
    a, e, f, g are prochiral.

    Exercise 6.2.2:

    a) re b) si c) re d) si e) either; if the Br adds on one end of the double dond it is re, but at the other it is si f) re

    Exercise 6.2.3:

    EA2pt3soln.png

    Exercise 6.2.4:

    EA2pt4soln.png

    Exercise 6.3.1:

    If the acid is regenerated at the end of the reaction, it isn't a reagent. It is a catalyst. It makes addition of water to the double bond occur much more quickly than if water acted alone, since water would never manage to protonate the alkene.

    Exercise 6.3.2:

    EA3pt2soln.png

    Exercise 6.3.3:

    EA3pt3soln.png

    Exercise 6.4.1:

    Two products are formed and they are enantiomers.

    EA4pt1soln.png

    Exercise 6.4.2:

    They are diastereomers. One chiral center has the same configuration in both compounds but the others are opposite.

    EA4pt2soln.png

    Exercise 6.4.3:

    The second bromine could occupy any of the secondary positions if there were a true carbocation. That doesn't happen; the second bromine occupies only the position next to the other bromine.

    EA4pt3soln.png

    Exercise 6.4.5:

    The nucleophile in the second step changes under different conditions.

    EA4pt5soln.png

    Exercise 6.4.6:

    EAbrprodsoln.png

    Exercise 6.5.2:

    EAmercacetatebase.png

    Exercise 6.5.3:

    EAmercreductionmech.png

    Exercise 6.5.4:

    EAalkoxymercuration.png

    Exercise 6.5.5:

    EAmercprodsoln.png

    Exercise 6.5.6:

    EAsolvomercprodsoln.png

    Exercise 6.6.1:

    MI5pt1.png

    Exercise 6.6.2:

    MI5pt2.png

    Exercise 6.6.3:

    MI5pt3.png

    Exercise 6.6.4:

    MI5pt4.png

    Exercise 6.6.5:

    MIApplicationDrillAnswers.png

    Exercise 6.6.6:

    MI4ConceptQAnswer.png

    Exercise 6.6.7:

    MI4drillanswers.png

    Exercise 6.6.8:

    MI4CumulativeAnswer.png

    Exercise 6.6.9:

    guanacastapeneanswers.png

    Exercise 6.6.10:

    PhyllanthocinAnswer.png

    Exercise 6.7.2:

    EAboranesynanti.png

    Exercise 6.7.3:

    Crowding is more severe in the structure on the left than in the structure on the right. The structure on the right, representing an approach to the transition state of the reaction, is more favorable than the other one.

    EAborane sterics.png

    Exercise 6.7.4:

    EAbh3thf.png

    Exercise 6.7.5:

    EAboranehgrgtsoln.png

    Exercise 6.7.6:

    EAfinalrgtsoln.png

    Exercise 6.7.7:

    EAfinalprodsoln.png

    Exercise 6.8.1:

    EAepoxexpectsoln.png

    Exercise 6.8.2:

    EAepoxselectionsoln.png

    Exercise 6.8.3:

    Allylalcoholsoln.png

    Exercise 6.8.4:

    D-(-)-tartrate is the (2S,3S)-isomer. L-(+)-tartrate is the (2R,3R)-isomer. Each chiral center is configured opposite to the corresponding one in the other molecule, so the molecules are enantiomers.

    Exercise 6.8.5:

    EpoxTichiralS.png

    Exercise 6.8.6:

    EcklonialactoneAnswer.png

    Exercise 6.8.7:

    chamobtusinAnswer.png

    Exercise 6.8.8:

    mesembrineAnswer.png

    Exercise 6.9.1:

    The chlorines can (weakly) share their electrons to fill the octet on carbon.

    EACCl2stable.png

    Exercise 6.9.2:

    The oxygen can π-donate to help fill the octet on the carbon.

    EAFecarbenessoln.png

    Exercise 6.9.3:

    Not only can the nitrogens π-donate to help fill the octet on carbon, but this is an aromatic system. It is planar, cyclic, fully conjugated, with an odd number of electron pairs in the π-system.

    EAarduengosoln.png

    Exercise 6.9.4:

    EAcpropexpectsoln.png

    Exercise 6.10.1:

    EAepoxelectrophile.png

    Exercise 6.10.2:

    EAsharplesselectrophile.png

    Exercise 6.10.3:

    EAoxidnRgtsoln.png

    Exercise 6.10.4:

    EAoxidnProdsoln.png

    Exercise 6.10.5:

    AloperineAnswer.png

    This page titled 6.14: Solutions for Selected Problems. is shared under a CC BY-NC 3.0 license and was authored, remixed, and/or curated by Chris Schaller via source content that was edited to the style and standards of the LibreTexts platform; a detailed edit history is available upon request.