Organic Chemistry
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Rationalize the ranking of the following ethers according to their ability to form explosive peroxides.
Considering the relative stabilities of the resulting alkyl radicals, determine which of the indicated carbon-hydrogen bonds would have a higher value of the bond dissociation energy.
Considering the relative stabilities of the resultant free radicals, identify which of the indicated carbon-halogen bonds would have a higher value of the bond dissociation energy.
Considering the relative stabilities of the resultant alkyl radicals, indicate which of the marked carbon-hydrogen bonds would have a higher value of the bond dissociation energy.
Determine which of the following radicals is the most stable, and thus, is most likely to be produced from an ether.
The following table shows a few common C–H bond dissociation energies for homolytic cleavages.
Write an equation to show how diphenylmethane reacts with an alkyl free radical to form a stable radical. Use the given information to explain why the formation of this radical is energetically favorable.
A graduate student was studying free radical halogenation reactions. She added NBS to a solution of 3-methylcyclopent-1-ene and irradiated the mixture with a sunlight lamp. After all of the added NBS was consumed, she found that the reaction resulted in four different isomeric products of the formula C6H9Br. Rank the four allylic radicals that produce the four isomeric products.
The following three alkenes are arranged in decreasing order of their bond rotational energy barriers. Consider their transition states to explain the difference in bond rotation energies.
Considering the stability of the generated radicals, does the encircled bond in compound A have a higher bond-dissociation energy than the encircled bond in compound B?
Provide an explanation for the preferential use of tert-amyl methyl ether (TAME) as a solvent over diethyl ether in terms of their structures.
(9Z,16Z)-octadeca-9,16-dienoic acid does not exist naturally. It has the same rate of oxidation as oleic acid, even though it has two cis-alkenes. Why?
i) Specify the hydrogen/s in the structure that is the easiest to remove for a bromine radical.
ii) Determine the number of secondary hydrogens.
Consider the radicals shown below:
Sort the radicals in order of decreasing stability. Determine if they are a tertiary, secondary, or primary radical.
Based on the bond-dissociation enthalpies, arrange the radicals below in order of increasing stability.
Rank the following reactive intermediates in order of decreasing reactivity:
In comparison to a secondary carbon radical, an allylic carbon radical is more stable. Why?
Which of the following best defines a radical in organic chemistry?
How does the electron deficiency of radicals relate to their orbital occupancy?
How does hyperconjugation stabilize radicals?
Which of the following statements best explains how R groups stabilize radicals through hyperconjugation?
Why are allylic and benzylic radicals more stable than tertiary radicals?
