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Chapter 20: Q30P (page 1038)

Rank the following radicals in decreasing order of stability. Classify each as primary, secondary, or tertiary.

(a)

(b)

(c)

(d)

Short Answer

Expert verified

radicals in order from most stable to least stable

Step by step solution

01

Free radicals

An atom or group of atoms containing odd or unpaired electron is known as the free radical. The unpaired electron is represented by a single unpaired dot in the formula. Free radicals are electrically neutral. They are highly reactive species formed by homolytic fission of a covalent bond.

02

Stability of free radicals

Tertiary alkyl radical is more stable than secondary alkyl radical which in turn is more stable than primary alkyl radical. However, methyl free radical which does not contain any alkyl group is the least stable.

03

Free radicals in decreasing order of stability

Tertiary allylic radical is the most stable than tertiary since it is stabilized by resonance while the primary radical is the least stable.

radicals in order from most stable to least stable

Resonance delocalization is particularly effective in stabilizing a radical.

tertiary allylic radical stabilized by resonance

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Most popular questions from this chapter

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

(b)

(c)

Phenols (pKa鈮� 10) are more acidic than other alcohols, so they are easily deprotonated by sodium hydroxide or potassium hydroxide. The anions of phenols (phenoxide ions) can be used in the Williamson ether synthesis, especially with very reactive alkylating reagents such as dimethyl sulfate. Using phenol, dimethyl sulfate, and other necessary reagents, show how you would synthesize methyl phenyl ether.

Tributylin hydride (Bu3SnH)is used synthetically to reduce alkyl halides, replacing a halogen atom with hydrogen. Free-radical initiators promote this reaction, and free-radical inhibitors are known to slow or stop it. You job is to develop a mechanism, using the following reaction as an example.

The following bond-dissociation enthalpies may be helpful:

(a) Propose initiation and propagation steps to account for this reaction.

(b) Calculate values of 螖贬 for your proposed steps to show that they are energetically feasible. (Hint: A trace of Br2 and light suggests it鈥檚 there only as an initiator, to create Brradicals. Then decide which atom can be extracted most favorably from the starting materials by the Brradical. That should complete the initiation. Finally, decide what energetically favored propagation steps will accomplish the reaction).

Show how you would synthesizefrom each compound. You may use any necessary reagents.

(a) heptanal

(b)oct - 1 - yne

(c) 2,3 - dimethylnon - 2 - ene

(d)octan - 2 - ol

(e) heptanoic acid

(f) CH3(CH2)5CN

Which of the following compounds are chiral? Draw each compound in its most symmetric conformation, star any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.

(a) meso-2,3-dibromo-2,3-dichlorobutane

(b) -2,3-dibromo-2,3-dichlorobutane

(c) (2R,3S)-2-bromo-3-chlorobutane

(d) (2R,3S)-2,3-dibromobutane

(e) (R,R)-2,3-dibromobutane

(f)

(g)

(h)
See all solutions

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