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Chapter 11

CHEM 2OB3 Chapter Notes - Chapter 11: Tupperware, Polystyrene, Steric Effects


Department
Chemistry
Course Code
CHEM 2OB3
Professor
Dr Mcnulty
Chapter
11

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Chapter 11: Radical Reacons
11.1 Radicals
- Homolyc 

Structure and Geometry of Radicals
- Carbocaon
- Carbanion
o  
!
- Carbon radical"
trigonal planar"

oStability #"
terary > secondary > primary
o$#
#"hyperconjugaon
o%bond dissociaon energies
(BDEs)
Resonance Structures of Radicals
-&'# 
()"*
#
- Resonance-stabilized radicals are even more stable than
terary radicals +,
- Vinylic radicals"

oVinylic radicals 

o#
11.2 Common Pa+erns in Radical Mechanisms
--#
-. )#
1. Homolyc cleavage
o-("Δ
hv
2. Addion of a pi bond
o$/#
3. Hydrogen abstracon

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o0"12

4. Halogen abstracon
o3#
5. Eliminaon
oAlpha (α) posion: #
o4567#
o%7"
6. Coupling
o8'
-9:.
-;
--<</
-:./;
11.3 Chlorinaon of Methane
A Radical Mechanism for Chlorinaon of Methane
-9#"###/#
"#/##
- Sum of propagaon steps gives the net reacon
o4#%/
o=%
chain reacon
oPolychlorinaon*%

Only pages 1-3 are available for preview. Some parts have been intentionally blurred.

-9##
o8'*/
%
Radical Iniators
-,##"#
- Radical iniator: #
/#
- Peroxides: -==-
- Acyl peroxides: *
*"
>#
==
o3+," 

Radical Inhibitors
- Radical inhibitor: ?
#
o, #/radical scavengers
o,@@*=
9
4/
o,@@(
#
/
#

#(
11.4 Thermodynamic Consideraons for Halogenaon
- Breaking bonds:("#
- Forming bonds:"#
-1#
o,/
- Iodinaon: #AB/#
- Fluorinaon: */##
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