Radical Reactions (Organic Chemistry)

Info from Klein 4e
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Last updated: June 1, 2024
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1. What picture best represents homolytic bond cleavage?
2. What picture best represents heterolytic bond cleavage?
Homolytic bond cleavage is when each element in the bond receives an electron. To show the movement of individual electrons (not an electron pair) we need to use fishook arrows
3. radicals have (effectively) a __________ geometry and are (effectively) ___ hybridized
Experimental evidence shows radicals are either trigonal planar or have a very shallow, rapidly inverting pyramid
trigonal planar, sp3
trigonal pyramidal, sp3
linear, sp
trigonal planar, sp2
4. Which radical is the most stable?
hyperconjugation
Primary
Methyl
Secondary
Tertiary
5. Which is the most stable radical?
conjugation. benzylic>allylic>tertiary
primary
allylic
tertiary
benzylic
6. Least stable radical?
methyl
secondary
primary
vinylic
7. What are the three basic stages of a radical reaction?
coupling, hydrogen abstraction, halogen abstraction
bromination, nucleophilic attack, homolytic cleavage
Initiation, propagation, and termination
alkylation, Friedel-crafts acylation, Nucleophilic aromatic substitution
8. What is a radical initiator?
an enzyme that cleaves a radical
A compound with a weak bond that uundergoes homolytic bond cleavage with ease
death
light
9. What is a radical inhibitor
light
A compound that prevents a chain process from getting started or continuing
activation energy
alkyl peroxides
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