Alkenes - University Of Illinois

Alkenes - University Of Illinois

Alkenes CnH2n sp2 hybridized carbons p p sp2 s H H C C H

H Alkenes Cl Cl Cl H cisCl Cl no rotation at C=C trans- HCl

geometric isomers Nomenclature 1. 2. 3. 4. 5. 6. Longest chain with C=C is parent. C numbered from end nearest to C=C. Designate cis- or trans- if necessary. Name substituents. Replace ane with ene ending. If more than one C=C, give smallest numbers and call diene or triene.

Nomenclature 1 2 3 4 6 5 8 7

trans- 2- octene cis- 2- octene trans- 5-methyl-3-propyl-1,3- hex adiene 1 3 2 4 5 3-propyl 6 5-methyl

Alkene - reactions electrons Lewis Base Lewis Base e- pair donor nucleophile Lewis Acid e- pair acceptor electrophile Addition Reactions + Hrxn = bonds broken - bonds formed Hrxn = (-bond + -bond) - (2 -bonds) < 0 exothermic Addition of HX H3C H

C C H H + H+ + Cl- reaction mechanism H3C H H C C H Cl H H3C H H C C H H Cl Lewis base

electrons nucleophile Lewis acid H+ electrophile Addition of HX step 1 H3C H C

C H H + H-Cl H+ + Cl- H+ 2o carbocation 1o carbocation Addition of HX 2o carbocation

1o carbocation most stable intermediate Stability of carbocations 3o > 2o > 1o carbocations are e- deficient electrophiles react with nucleophile Lewis acids Lewis base Addition of HX step 2 major product minor product

Markovnikovs Rule major product minor product 2-chloropropane 1-chloropropane C with the most H gets the H

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