Chem241a_Lecture_17

Chem241a_Lecture_17 - Or ganic Chemistry 241a Prof. Bogdan...

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Unformatted text preview: Or ganic Chemistry 241a Prof. Bogdan Olenyuk Contact Information Office: Old Chemistry 309 olenyuk@email.arizona.edu Phone: (520) 626-0754 Course web site: http://www.chem.arizona.edu/courseweb/074/CHEM241A1_2/FrameSet.html Chapters 6 & 7: Alkenes Stability of alkenes Electrophilic additions to alkenes Structure and stability of cabocations Reactions of alkenes Today we will cover: Reading Assignment: McMurry (the BOOK), Ch. 6.6-6.11, 7.1-7.2 Comparing Stabilities of Alkenes Evaluate heat given off when C=C is converted to C-C More stable alkene gives off less heat trans-Butene generates 5 kJ less heat than cis-butene Hyperconjugation Electrons in neighboring filled orbital stabilize vacant antibonding orbital net positive interaction Alkyl groups are better than H Electrophilic Addition of Alkenes General reaction mechanism: electrophilic addition Attack of electrophile (such as HBr) on bond of alkene Produces carbocation and bromide ion Carbocation is an electrophile, reacting with nucleophilic bromide ion Two step process First transition state is high energy point Electrophilic Addition Energy Path Electrophilic Addition for Preparations The reaction is successful with HCl and with HI as well as HBr HI is generated from KI and phosphoric acid Orientation of Electrophilic Addition:...
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Chem241a_Lecture_17 - Or ganic Chemistry 241a Prof. Bogdan...

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