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Chapter 15: Q32. (page 570)

Questions: Why is a benzylic C-H bond unusually weak?

Short Answer

Expert verified

Answer

Benzylic C-H bond is unusually weak because the cleavage of the C-H bond gives a 1o radical, which is stabilized by resonance.

Step by step solution

01

Stability

The presence of an unpaired electron forms a radical. It is represented by a dot.It is unstable and highly reactive. Its stability is governed by the degree of radical formed.

02

Explanation by resonance

Representation of resonance structures

Due to the resonance stabilization of benzylic radical, the C-H bond cleavage is easy.

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Most popular questions from this chapter

Question: Identify the structure of a minor product formed from the radical chlorination of propane, which has molecular formula C3H6Cl2 and exhibits the given 1H NMR spectrum.

Question: In cells, vitamin C exists largely as its conjugate base X. X is an antioxidant because radicals formed in oxidation processes abstract the labeled H atom, forming a new radical that haltsoxidation. Draw the structure of the radical formed by H abstraction, and explain why this Hatom is most easily removed.

Question: The triphenylmethyl radical is an unusual persistent radical present in solution in equilibrium with its dimer. For 70 years the dimer was thought to be hexaphenylethane, but in 1970, NMR data showed it to be A.

a. Why is the triphenylmethyl radical more stable than most other radicals?

b. Use curved arrow notation to show how two triphenylmethyl radicals dimerize to form A.

c. Propose a reason for the formation of A rather than hexaphenylethane.d. How could 1 H and 13C NMR spectroscopy be used to distinguish between hexaphenylethane and A?

Question. Ethers are oxidized with to form hydroperoxides that decompose violently when heated. Draw a stepwise mechanism for this reaction.

Question: Devise a synthesis of each compound from cyclopentane and any other required organic or inorganic reagents.

a.

b.

c.

d.

e.
See all solutions

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