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Chapter 6: Problem 6.32 (page 241)

(a) Draw in the curved arrows to show how A is converted to B in Step [1]. (b) Identify X, using the curved arrows drawn for Step [2].

Short Answer

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Answer

(a)

Conversion of A to B

(b)

Conversion of B to X

Step by step solution

01

Step-by-Step SolutionStep 1: Proton Transfer reaction

In acid-base reactions, the base shares its electron density with the most acidic hydrogen atom of the acid. Thus, a proton from the acid is transferred to the base. This step in the acid-base reaction is called the proton transfer step.

02

Addition reaction

When two elements and/or compounds combine to form a new compound, the reaction is called an addition reaction.

03

Determining the products of the given reaction

The curved arrows to show the conversion of A to B are shown hereunder:


Conversion of A to B

As is indicated by the curved arrows, the Bromide anion is added to the ring. One of the two bonds of oxygen with the ring breaks off. The new compound thus formed is 1-bromide-2-hydroxylcyclohexane.


Conversion of B to X

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Most popular questions from this chapter

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 Diels–Alder reaction, a powerful reaction discussed in Chapter 16, occurs when a 1,3- diene such as A reacts with an alkene such as B to form the six-membered ring in C.

a. Draw curved arrows to show how A and B react to form C.

b. What bonds are broken and formed in this reaction?

c. Would you expect this reaction to be endothermic or exothermic?

d. Does entropy favor the reactants or products?

e. Is the Diels–Alder reaction a substitution, elimination, or addition?

Calculate ΔH° for each oxidation reaction. Each equation is balanced as written; remember to take into account the coefficients in determining the number of bonds broken or formed.

[ ΔH∘for O2=497kJ/mol ; ΔH∘for one C=O in CO2=535kJ/mol]

a.role="math" localid="1648191068323" CH4+2O2→CO2+2H2O

b.2CH4+7O2→4CO2+6H2O

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.

Classify each transformation as substitution, elimination, or addition.

a.

b.
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