MWF_26 - Organic Lecture Series CH 310/318 M LECTURE 26...

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Organic Lecture Series 1 CH 310/318 M LECTURE 26 Textbook Assignment: Chapter 8- Haloalkanes Today’s Topics: The Free radical halogenation The Free radical halogenation Notice & Announcements: XM 2- grading in progress Organic Lecture Series 2 Haloalkanes Haloalkanes Chapter 8 Chapter 8
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Organic Lecture Series 3 • Bond Dissociation Enthalpies (BDE) CH 2 =CH- H 2 =CH 3 - H 3 3 2 - H 3 2 (CH 3 ) 2 CH- H 3 ) 2 3 ) 3 C- H 3 ) 3 C C 6 H 5 2 - H C 6 H 5 2 2 =CHCH 2 - H 2 =CHCH 2 Benzyl Allyl Vinyl Methyl Ethyl Isopropyl tert- Butyl 372 (89) 376 (90) 405 (97) 414 (99) 421 (101) 439 (105) 464 (111) Hydrocarbon Radical Name of Radical Δ H 0 kJ (kcal)/mol Vinylic Benzylic Allylic Type of Energetics Energetics Increasing E Increasing Stability Organic Lecture Series 4 Radical: Radical: any chemical species that contains one or more unpaired electrons. –Radicals are formed by homolytic homolytic bond bond cleavage cleavage. –The order of stability of alkyl radicals is 3° > 2° > 1° > methyl. Mechanisms Mechanisms
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Organic Lecture Series 5 – The order of stability of alkyl radicals is 3° > 2° > 1° > methyl. CH 3 2 OO C H 2 3 Cl 3 3 3 3 2 O 3 OCH 2 3 Δ H 0 = +159 kJ/mol (+38 kcal/mol) Ethoxy radicals Diethyl peroxide 80° + Δ H 0 = +376 kJ/mol (+90 kcal/mol) Methyl radicals Ethane heat + Chlorine atoms Chlorine light + Δ H 0 = +247 kJ/mol (+59 kcal/mol) Mechanisms Mechanisms
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This note was uploaded on 11/07/2010 for the course CH 101 taught by Professor Dude during the Spring '10 term at Williamson.

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MWF_26 - Organic Lecture Series CH 310/318 M LECTURE 26...

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