Chapter 23, Problem 23.66P

Interpretation Introduction

(a)

Interpretation:

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is to be shown.

Concept introduction:

The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 23.66P

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is shown below.

Explanation of Solution

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s involves the two steps. These two steps are shown below.

Figure 1

Figure 2

The first step of the reaction involves the bromination of cyclohexanone in the presence of acetic acid. It results in the formation of $2-$ bromocyclohexanone. In the second step of the reaction, nucleophilic substitution takes place. The compound, $2-$ bromocyclohexanone reacts with ${\text{NaOCH}}_{\text{3}}$ to produce $2-$ methoxycyclohexanone.

Conclusion

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s is shown in Figure 1 and Figure 2.

Interpretation Introduction

(b)

Interpretation:

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is to be shown.

Concept introduction:

The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 23.66P

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is shown below.

Explanation of Solution

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s involves the two steps. These two steps are shown below.

Figure 3

Figure 4

The full form of LDA is lithium diisopropylamide. It is a strong base. In the first step, cyclohexanone reacts with LDA to form an intermediate, which is followed by a reaction with allyl bromide to produce $2-$ allylcyclohexanone. In the next step, it undergoes reduction with ${\text{NaBH}}_{\text{4}}$ in the presence of ${\text{H}}_{\text{3}}{\text{O}}^{+}$ to give $2-$ allylcyclohexanol.

Conclusion

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s is shown in Figure 3 and Figure 4.

Interpretation Introduction

(c)

Interpretation:

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is to be shown.

Concept introduction:

The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 23.66P

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is shown below.

Explanation of Solution

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s involves the two steps. These two steps are shown below.

Figure 5

Figure 6

The full form of LDA is lithium diisopropylamide. It is a strong base. In the first step, cyclohexanone reacts with LDA to form an intermediate, which is followed by a reaction with methyl bromide to produce $2-$ methylcyclohexanone. In the next step, it further reacts with ethyl bromide to give $2-$ ethyl $-6-$ methylcyclohexanone.

Conclusion

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s is shown in Figure 5 and Figure 6.

Interpretation Introduction

(d)

Interpretation:

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is to be shown.

Concept introduction:

The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 23.66P

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is shown below.

Explanation of Solution

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s involves the three steps. These three steps are shown below.

Figure 7

Figure 8

Figure 9

The first step of the reaction involves the bromination of cyclohexanone in the presence of ${\text{CH}}_{\text{3}}\text{COOH}$. It results in the formation of $2-$ bromocyclohexanone. It is followed by reaction with ${\text{Li}}_{\text{2}}{\text{CO}}_{\text{3}}$ in the presence of $\text{LiBr}$ and DMF to give cyclohex $-2-$ enone. In the last step, cyclohex $-2-$ enone reacts with ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{CuLi}$ in the presence of ${\text{H}}_{\text{3}}{\text{O}}^{+}$ to give $3-$ ethylcyclohexanone.

Conclusion

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s is hown in Figure 7, Figure 8 and Figure 9.

Interpretation Introduction

(e)

Interpretation:

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is to be shown.

Concept introduction:

The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 23.66P

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is shown below.

Explanation of Solution

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s involves the three steps. These three steps are shown below.

Figure 10

Figure 11

Figure 12

The full form of LDA is lithium diisopropylamide. It is a strong base. In the first step, cyclohexanone reacts with LDA to form an intermediate, which is followed by a reaction with ethyl bromide to produce $2-$ ethylcyclohexanone. In the next step, it further reacts with LDA in the presence of ethyl bromide to give $2,6-$ diethylcyclohexanone. The last step involves bromination of $2,6-$ diethylcyclohexanone to form $2-$ bromo $-2,6-$ diethylcyclohexanone, which reacts with ${\text{Li}}_{\text{2}}{\text{CO}}_{\text{3}}$ in the presence of $\text{LiBr}$ and DMF to give a desired product.

Conclusion

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s is hown in Figure 10, Figure 11 and Figure 12.

Interpretation Introduction

(f)

Interpretation:

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is to be shown.

Concept introduction:

The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 23.66P

The synthesis of a given compound from cyclohexanone and organic halides having $\le 4\text{C}$’s is shown below.

Explanation of Solution

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s involves the three steps. These three steps are shown below.

Figure 13

Figure 14

The first step involves the bromination of cyclohexanone to give bromo product, which on reaction with ${\text{Li}}_{\text{2}}{\text{CO}}_{\text{3}}$ in the presence of $\text{LiBr}$ and DMF to produce cyclohex-2-enone. It reacts with LDA in the presence of ethyl bromide to give $6-$ ethylcyclohex $-2$-enone. It further reacts with $\text{NaOEt}$ to give a desired product.

Conclusion

The formation of the given product from cyclohexanone and organic halides having $\le 4\text{C}$’s is shown in Figure 13 and Figure 14.