The use of curved arrows is a powerful tool that illustrates even complex reactions.

a. Add curved arrows to show how carbocation A is converted to carbocation B. Label each new bond formed. Similar reactions have been used in elegant synthesis of steroids.

b. Draw the product by following the curved arrows. This reaction is an example of a [3,3] sigma tropic rearrangement, as we will learn in chapter 27.

Short Answer

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Answer

a.

Rearrangement of the carbocation A

The formation of the carbocation B

The new sigma bonds in carbocation B

b.

The products of the reaction b

Step by step solution

01

Step-by-Step SolutionStep 1: Synthesis of the organic compounds

The synthesis of the organic compounds is done by planning a certain group of reactions by using readily available starting materials. The synthesis happens by using more than one step at a time.

The proper selectivity of the reagents is essential for the synthesis of organic compounds.

Arrows are used to describe chemical reactions. The use of curved arrows demonstrates the movement of the electron pairs for understanding the mechanism of the reactions during organic synthesis.

02

The conversion of carbocation A to carbocation B.

The carbocation A is converted into carbocation B as shown in the following structure:Rearrangement of the carbocation A

The arrows indicate the movement of electrons in the above structure. In the following structure, the carbocation B is finally formed.The formation of the carbocation B

The new sigma bonds in carbocation B

b. The products of the given reaction are as follows:

The products of the reaction b

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Most popular questions from this chapter

Draw an energy diagram for each reaction. Label the axes, the starting material, product, transition state, ΔH°, and Ea.

a.a concertedwith ΔH°=-80kJ/moland Ea=16kJ/mol.

b. a two-step reaction, ABC, in which the relative energy of the compounds is A<C<B, and the step ABis rate-determining.

As we will learn in Section 15.12, many antioxidants—compounds that prevent unwanted radical oxidation reactions from occurring—are phenols, compounds that contain an OH group bonded directly to a benzene ring.

  1. Explain why homolysis of the O-H bond in phenol requires considerably less energy than homolysis of the O-H bond in ethanol (362 kJ/mol vs 438 kJ/mol).
  2. Why is the C-O bond in phenol shorter than C-O bond in ethanol?

The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:

a. Add curved arrows to show the movement of the electrons in each step.

b. Write the rate equation for this reaction, assuming the first step is rate-determining.

c. If the concentration of were increased 10 times, what would happen to the rate of the reaction?

d. If the concentrations of both and were increased 10 times, what would happen to the rate of the reaction?

e. Classify the conversion of acetyl chloride to methyl acetate as an addition, elimination, or substitution.

Draw the products of homolysis or heterolysis of each indicated bond. Use electronegativity differences to decide on the location of charges in the heterolysis reaction. Classify each carbon reactive intermediate as a radical, carbocation, or carbanion.

a.

b.

a. Which Keqcorresponds to a negative value of localid="1648198317845" ΔG, localid="1648198334107" Keq=1000 or Keq= 0.001 ?

b. Which Keqcorresponds to a lower value oflocalid="1648198364090" ΔG, localid="1648198396853" Keq=10-2or localid="1648198411007" Keq=10-5?

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