Chem 232 Lecture 12 - UIC Department of Chemistry - University of ...
Chem 232 Lecture 12 - UIC Department of Chemistry - University of ... Chem 232 Lecture 12 - UIC Department of Chemistry - University of ...
Anti Addition..–: Br:....Br..:..Br..:attack of bromide (Br – ) fromopposite side C-Br bond thatis breaking gives anti product..:University of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 26Lecture 12: February 1826
Hyperconjugation (σ C-H →π C=C )Increases Rate of HalogenationHC C C HHσ➞∏donationalkeneH HH HH 3 C HH HH 3 C HH 3 C HH 3 C CH 3H 3 C CH 3relative rate (krel)1615400920,000• more alkyl groups attached to double bond ➡• more σ➞π orbital donation/overlap ➡• double bond has more electron density ➡• double bond is a stronger nucleophile (Lewis base) ➡• reacts faster with electrophiles like Br-BrUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 27Lecture 12: February 1827
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Anti Addition..–: Br:....Br..:..Br..:attack <strong>of</strong> bromide (Br – ) fromopposite side C-Br bond thatis breaking gives anti product..:<strong>University</strong> <strong>of</strong> Illinois<strong>UIC</strong>at Chicago CHEM <strong>232</strong>, Spring 2010Slide 26<strong>Lecture</strong> <strong>12</strong>: February 1826
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