CHEM 353 Study Guide - Quiz Guide: Allyl Group, Nucleophilic Conjugate Addition, Stereochemistry
2 Aug 2014
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Previous material: (cid:120) orbitals, structure, bonding, reactions and synthesis of alkenes (cid:120) stability of carbocations and radicals (cid:120) preparation of alkenes (cid:120) reactions of alkenes. Kinetic versus thermodynamic product (cid:120) diels-alder reaction the nature of the diene & dienophile stereochemistry of cycloaddition reaction. The allyl group (12. 11): (cid:120) vinylic versus allylic positions. Indicate the vinylic and allylic hydrogen atoms in the following molecule: Allylic carbocations and sn1 reactions: (cid:120) a tertiary allylic halide undergoes solvolysis (sn1) faster than a simple tertiary alkyl halide - for the molecules below, the relative rate of reaction with etoh is 123:1. Ch3 (cid:120) delocalization of electrons in the allylic double bond stabilizes the carbocation intermediate (resonance stabilization) Rationalize the observed rate of solvolysis of a tertiary allylic halide versus a simple tertiary alkyl halide. Draw an orbital diagram of the allylic carbocation. Explain the following identical product distribution obtained from two different starting materials.
