Concept explainers
Interpretation:Significance of the dashed bonds in the structure of the non-classical cation should be given and the feature that makes this cation non-classical should be identified.
Concept introduction:A classical carbocation represented as
Classical carbocation prefers to be tri-coordinated and achieve stabilization via hyperconjugation. This indicates that an adjacent
A non-classical cation is a unique carbocation that involves the delocalization of electron density of filled bonding orbital over three carbons. It exists for systems such as phenonium ions,norbornyltosylates, brosylate, and nortricyclonium cations. They can be understood as carbocation that is a transition state for two asymmetric equilibrium cations.
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EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
- What is regioselectivity due to? a) On the stability differences of carbocations b) On the properties of the second stage nucleophile c) From steric hindrance d) On the mutual affinity of hydrogen atomsarrow_forward(a) A compound known to be a substituted cyclohexanone derivative has lamda max of 235 nm. Could this compound be a conjugated dienone? explain (b) (i)For this compound, how many nm must be accounted for by substituents? (ii) What are the substituents and the points of substitution that may occur having accounted for the 20nm?arrow_forward(b) Is UV spectroscopy a correct method to distinguish between the Rectant and Productarrow_forward
- Although dehydrohalogenation occurs with anti periplanar geometry,some eliminations have syn periplanar geometry. Examine the startingmaterial and product of attached elimination, and state whether the elimination occurs with syn or anti periplanar geometry.arrow_forwardWould this be correct crotylboration?arrow_forwardAlthough dehydrohalogenation occurs with anti periplanar geometry,some eliminations have syn periplanar geometry. Examine the startingmaterial and product of attached elimination, and state whether theelimination occurs with syn or anti periplanar geometry.arrow_forward
- Draw the pi molecular orbital (MO) diagrams for cyclopentadiene and maleic anhydride, label whether the new bond formation in this Diels-Alder reaction will be suprafacial or antarafacialarrow_forwardWhat is the major benefit of refluxing? Why might reflux conditions be required for this reaction (Friedel-Crafts Alkylation)?arrow_forwardIllsutrate the Energy diagram for carbocation formation in two different SN1 reactions ?arrow_forward