Why did breaking the P-C single bond lead to the formation of 2 species containing a free radical (ie. where did those 2 electrons come from)?

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3. Why did breaking the P-C single bond lead to the formation of 2 species containing a
free radical (ie. where did those 2 electrons come from)?
4. Do you think the photoinitiator 2-hydroxy-2-methylpropiophenone would require a
shorter or longer wavelength of light to create a free radical? Explain your answer
using the table provided in question #2 (be specific). The structure of 2-hydroxy-2-
methylpropiophenone is shown below.
CH3
Figure 5: Structure of 2-hydroxy-2-
methylpropiophenone. The wavy line shows
OH the bond that is photo-sensitive (ie. the bond
that will be broken by light). (Taken from
Tehfe et al. 2013, http://www.mdpi.com/2076-
3417/3/2/490/htm)
ČH3
5. Why is the PEGDA monomer soluble in water, but the polymer is not? In other
words, why do you think forming a large molecule would lead to the formation of a
solid? (Hint: think about the movement of molecules in a liquid vs solid phase).
6. Thinking about the octet rule, why do you think many free radicals are very reactive
and unstable?
7. Peroxides are often used as free radical initiators of polymerization reactions.
However, ethers are not often used for this purpose. Looking at the structures of the
two species and also using the table provided in question #2, why do you think
peroxides are a better choice? Be specific.
(а)
Figure 6: (a) The structure of benzoyl peroxide, an example of a commonly used
free radical initiator for polymerization (http:/len.academic.ru/dic.nsf/enwiki/425984).
(b) The structure of benzyl ether, which looks similar to benzoyl peroxide, but
contains an ether linkage and not a peroxide linkage. Benzyl ether it is not
commonly used as a free radical initiator for polymerization.
(http://tinyurl.com/hstzk32).
Transcribed Image Text:3. Why did breaking the P-C single bond lead to the formation of 2 species containing a free radical (ie. where did those 2 electrons come from)? 4. Do you think the photoinitiator 2-hydroxy-2-methylpropiophenone would require a shorter or longer wavelength of light to create a free radical? Explain your answer using the table provided in question #2 (be specific). The structure of 2-hydroxy-2- methylpropiophenone is shown below. CH3 Figure 5: Structure of 2-hydroxy-2- methylpropiophenone. The wavy line shows OH the bond that is photo-sensitive (ie. the bond that will be broken by light). (Taken from Tehfe et al. 2013, http://www.mdpi.com/2076- 3417/3/2/490/htm) ČH3 5. Why is the PEGDA monomer soluble in water, but the polymer is not? In other words, why do you think forming a large molecule would lead to the formation of a solid? (Hint: think about the movement of molecules in a liquid vs solid phase). 6. Thinking about the octet rule, why do you think many free radicals are very reactive and unstable? 7. Peroxides are often used as free radical initiators of polymerization reactions. However, ethers are not often used for this purpose. Looking at the structures of the two species and also using the table provided in question #2, why do you think peroxides are a better choice? Be specific. (а) Figure 6: (a) The structure of benzoyl peroxide, an example of a commonly used free radical initiator for polymerization (http:/len.academic.ru/dic.nsf/enwiki/425984). (b) The structure of benzyl ether, which looks similar to benzoyl peroxide, but contains an ether linkage and not a peroxide linkage. Benzyl ether it is not commonly used as a free radical initiator for polymerization. (http://tinyurl.com/hstzk32).
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