CHEM 282 Study Guide - Final Guide: Cyclopropane, Hydroboration, Sulfur Trioxide
23 Mar 2018
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P orbital on a c adjacent to a double bond, p orbital can come form another double/triple bond, empty p orbital of carbocation, radical p orbital. Allylic bromination: propene reacts w nbs (provides a low conc of br) in presence of light or peroxide. Electrophilic attack on alkadienes: 1,3-butadiene w middle bond shorter due to non-equal contributing resonance forms. Low temp favours 1,2-addition under kinetic control, this forms the fastest. High temp favours 1,4-addition bc it overcomes higher activation e and forms most sub/stable alkene under thermodynamic control. Diels-alder: forms cyclohexene prod, two new sigma bonds are formed at the expense of two pi bonds. Want e- donating groups on dienes and e- withdrawing groups on. Favour endo rxs when rx is kinetically controlled. Exo= equatorial position sub (thermos prod) endo is major prod bc unhybridized p orbitals can overlap creating a secondary mo interaction stabilizes it.
