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Chapter 15: Q58. (page 570)

Question: Devise a synthesis of 1-methylcyclohexene oxide from methylcyclohexane. You may use any other required organic or inorganic reagents.

Short Answer

Expert verified

In a radical reaction, one or two atoms are substituted by radicals (atoms with incomplete valence electrons) following a continuous step of the mechanism.

Step by step solution

01

Radical reactions

In a radical reaction, one or two atoms are substituted by radicals (atoms with incomplete valence electrons) following a continuous step of the mechanism.

02

Halogenations of alkanes

In halogenation of alkanes, a weaker C-H bond is broken, and a C-X bond is formed (X - Cl, Br, I).

03

 Step 3: Synthesis reaction

  1. Halogenation of methylcyclohexane forms a C-Br bond.

2. The base eliminates HBr, and alkene is formed.

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Most popular questions from this chapter

Question: Which C-H bond in each compound most readily broken during radical halogenation?

a.

b.

c.

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:A and B, isomers of molecular formula C3H5Cl3 , are formed by the radical chlorination of a dihalide C of molecular formula C3H6Cl2 .

(a) Identify the structures of A and B from the following NMR data:

Compound A: singlet at 2.23 and singlet at 4.04 ppmCompound B: doublet at 1.69, multiplet at 4.34, and a doublet at 5.85 ppm

(b) What is the structure of C?

Question:Draw the products formed in each reaction and include the stereochemistry around any stereogenic centers.

a.

b.

c.

d.

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.
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