Chapter 11, Problem 11.61AP

Interpretation Introduction

(a)

Interpretation:

The synthesis of $\text{2-}$ ethoxy $\text{-3-}$ methylbutane from $\text{3-}$ methyl $\text{-1-}$ butene is to be drawn.

Concept introduction:

Oxymercuration reaction is a type of reaction in which an alkene gets converted to alcohol. The mercuric acetate is used in the reaction as a reagent. This reagent attacks the alkene to form a cyclic intermediate compound which further undergoes reduction to form alcohol.

Answer to Problem 11.61AP

The synthesis of $\text{2-}$ ethoxy $\text{-3-}$ methylbutane from $\text{3-}$ methyl $\text{-1-}$ butene is shown below.

Explanation of Solution

The mercuric acetate $\text{Hg}{\left(\text{OAc}\right)}_{\text{2}}$ in $\text{THF,}{\text{H}}_{\text{2}}\text{O}$ solvent reacts with $\text{3-}$ methyl $\text{-1-}$ butene to form an intermediate product which is reduced by the addition of ${\text{NaBH}}_{\text{4}}$ in the reaction mixture. The end product formed in the reaction is ether due to the use of $\text{EtOH}$ as solvent.

Figure 1

Conclusion

The route of synthesis of the formation of $\text{2-}$ ethoxy $\text{-3-}$ methylbutane from $\text{3-}$ methyl $\text{-1-}$ butene is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The synthesis of $\text{2-}$ ethoxy $\text{-3-}$ methylbutane from $\text{2-}$ methyl $\text{-2-}$ butanol is to be drawn.

Concept introduction:

The substances which on addition removes oxygen atom or hydrogen atom from the other substance, that is, reduces the other substances are known as reducing agents. Reducing agents themselves get oxidized. Strong reducing agents like ${\text{KMnO}}_{\text{4}}$, reduces all the carbonyl groups present in a compound into alcohol.

Answer to Problem 11.61AP

The synthesis of $\text{2-}$ ethoxy $\text{-3-}$ methylbutane from $\text{2-}$ methyl $\text{-2-}$ butanol is shown below.

Explanation of Solution

The treatment of $\text{2-}$ methyl $\text{-2-}$ butanol with methyl iodide in presence of a strong base forms the desired product as shown below.

Figure 2

Conclusion

The route of synthesis of the formation of $\text{2-}$ ethoxy $\text{-3-}$ methylbutane from $\text{2-}$ methyl $\text{-2-}$ butanol is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The synthesis of $4,4\text{-}$ dimethyl $\text{-1-}$ pentanol from ethylene oxide is to be drawn.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases.

Answer to Problem 11.61AP

The synthesis of $4,4\text{-}$ dimethyl $\text{-1-}$ pentanol from ethylene oxide is shown below.

Explanation of Solution

The reaction of tert-butyl bromide with $\text{Mg}$ metal in presence of ether forms the Grignard reagent. This on further reaction with ethylene oxide followed by the hydrolysis forms the desired product as shown below.

Figure 3

Conclusion

The route of synthesis of the formation of $4,4\text{-}$ dimethyl $\text{-1-}$ pentanol from ethylene oxide is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The synthesis of the given compound from the compounds that contain $\le 2$ carbons is to be drawn.

Concept introduction:

Oxidation is the process in which there is an addition of oxygen atom or removal of hydrogen atom. The agents used for the oxidation reaction is known as oxidizing agents. It oxidizes the other substance and gets reduced in the reaction. The common oxidizing agents are nitric acid, oxygen and potassium dichromate.

Answer to Problem 11.61AP

The synthesis of the given compound from the compounds that contain $\le 2$ carbons is shown below.

Explanation of Solution

The reaction of ethnethiol with $\text{2-}$ bromoethanol results in the formation of an alcohol. Then, the alcohol undergoes oxidation reaction in presence of $\text{PCC}$ gives aldehyde which on further reaction with wittig reagent, ethylidene triphenylphosphorane, forms the desired product as shown below.

Figure 4

Conclusion

The synthesis of the given compound from the compounds that contain $\le 2$ carbons is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

The synthesis of the given compound from an alkene is to be drawn.

Concept introduction:

Oxidation is the process in which there is an addition of oxygen atom or removal of hydrogen atom. The agents used for the oxidation reaction is known as oxidizing agents. It oxidizes the other substance and gets reduced in the reaction. The common oxidizing agents are nitric acid, oxygen and potassium dichromate.

Answer to Problem 11.61AP

The synthesis of the given compound from an alkene is shown below.

Explanation of Solution

The reaction of $\text{1-}$ methylcyclopent $\text{-1-}$ with $m\text{-CPBA}$ followed by the hydrolysis results in the formation of the desired product as shown below.

Figure 5

Conclusion

The synthesis of the given compound from an alkene is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

The synthesis of cyclohexyl isopropyl ether from cyclohexene is to be drawn.

Concept introduction:

Oxidation is the process in which there is an addition of oxygen atom or removal of hydrogen atom. The agents used for the oxidation reaction is known as oxidizing agents. It oxidizes the other substance and gets reduced in the reaction. The common oxidizing agents are nitric acid, oxygen and potassium dichromate.

Answer to Problem 11.61AP

The synthesis of cyclohexyl isopropyl ether from cyclohexene is shown below.

Explanation of Solution

The compound, $\text{1-}$ methylcyclopent $\text{-1-}$ undergoes oxidation reaction in presence of ${\text{KMnO}}_{\text{4}}$ and a base to produse the desired cis diol as shown below.

Figure 6

Conclusion

The synthesis of cyclohexyl isopropyl ether from cyclohexene is shown Figure 6.

Interpretation Introduction

(g)

Interpretation:

The synthesis of cyclohexyl isopropyl ether from cyclohexene is to be drawn.

Concept introduction:

Oxymercuration reaction is a type of reaction in which an alkene gets converted to alcohol. The mercuric acetate is used in the reaction as a reagent. This reagent attacks the alkene to form a cyclic intermediate compound which further undergoes reduction to form alcohol.

Answer to Problem 11.61AP

The synthesis of cyclohexyl isopropyl ether from cyclohexene is shown below.

Explanation of Solution

The mercuric acetate $\text{Hg}{\left(\text{OAc}\right)}_{\text{2}}$ in $\text{THF,}{\text{H}}_{\text{2}}\text{O}$ solvent reacts with cyclohexene to form an intermediate product which is reduced by the addition of $\text{NaH}$ in the reaction mixture. Simultaneously, it reacts with the isopropyliodide which results in the formation of the desired product as shown below.

Figure 7

Conclusion

The synthesis route of cyclohexyl isopropyl ether from cyclohexene is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation:

The synthesis of the given compound from $\text{3-}$ methyl $\text{-1-}$ butene is to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases

Answer to Problem 11.61AP

The synthesis of the given compound from $\text{3-}$ methyl $\text{-1-}$ butene is shown below.

Explanation of Solution

Bromination of alkene occurs with $\text{HBr}$ in presence of ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ forms $\text{1-}$ bromo $\text{-3-}$ methylbutane. The addition follows anti-Markovnikov’s rule. Furthre, it reacts with magnesium metal to forms the desired Grignard reagent.

Grigmard reagent reacts with the ethylene oxide followed by the hydrolysis to form an alcohol which upon oxidation by ${\text{CrO}}_{\text{3}}$ gives the desired product as shown below.

Figure 8

Conclusion

The synthesis of the given compound from $\text{3-}$ methyl $\text{-1-}$ butene is shown in Figure 8.

Interpretation Introduction

(i)

Interpretation:

The synthesis of the given compound from $\text{3-}$ methyl $\text{-1-}$ pentene is to be drawn.

Concept introduction:

An epoxide is cyclic ether. It can be prepare by the reaction of alkene with percarboxylic acid with removal of carboxylic acid. An epoxide undergoes ring opening reactions with an acid to give a product with inversion configuration.

Oxidation is the process in which there is an addition of oxygen atom or removal of hydrogen atom. The agents used for the oxidation reaction is known as oxidizing agents. It oxidizes the other substance and gets reduced in the reaction. The common oxidizing agents are nitric acid, oxygen and potassium dichromate.

Answer to Problem 11.61AP

The synthesis of the given compound from $\text{3-}$ methyl $\text{-1-}$ pentene is shown below.

Explanation of Solution

Epoxidation of $\text{3-}$ methyl $\text{-1-}$ pentene followed by the hydrolysis which results in the formation of an alcohol. On further oxidation of alcohol in presence of ${\text{CrO}}_{\text{3}}$ forms the desired product as shows below.

Figure 9

Conclusion

The synthesis route of the given compound from $\text{3-}$ methyl $\text{-1-}$ pentene is shown in Figure 9.

Interpretation Introduction

(j)

Interpretation:

The synthesis of the given compound from $\text{2-}$ methylpropene is to be drawn.

Concept introduction:

An epoxide is cyclic ether. It can be prepare by the reaction of alkene with percarboxylic acid with removal of carboxylic acid. An epoxide undergoes ring opening reactions with an acid to give a product with inversion configuration.

Oxidation is the process in which there is an addition of oxygen atom or removal of hydrogen atom. The agents used for the oxidation reaction is known as oxidizing agents. It oxidizes the other substance and get reduced in the reaction. The common oxidizing agents are nitric acid, oxygen and potassium dichromate.

Answer to Problem 11.61AP

The synthesis of the given compound from $\text{2-}$ methylpropene is shown below.

Explanation of Solution

Epoxidation of $\text{2-}$ methyl propene followed by the acidic hydrolysis which results in the formation of an alcohol. On further oxidation of alcohol in presence of ${\text{CrO}}_{\text{3}}$ forms the desired product as shown below.

Figure 10

Conclusion

The synthesis route of the given compound from $\text{2-}$ methylpropene is shown in Figure 10.

Interpretation Introduction

(k)

Interpretation:

The synthesis of given compound from the allyl chloride is to be drawn.

Concept introduction:

The nucleophilic substitution reactions depend upon the nucleophilicity and concentration of the nucleophile. There are two types of nucleophilic substitution reaction.

The ${\text{S}}_{\text{N}}2$ reaction is a nucleophilic substitution bimolecular single step reaction in which the addition of nucleophile and removal of leaving group takes place simultaneously

Answer to Problem 11.61AP

The synthesis of given compound from the allyl chloride is shown below.

Explanation of Solution

Allyl chloride reacts with $\text{NaOEt}$ to form the substitution product which on ozonolysis forms the desired product as shown below.

Figure 11

Conclusion

The synthesis of given compound from the allyl chloride is shown in Figure 11.

Interpretation Introduction

(l)

Interpretation:

The synthesis of the given compound is to be drawn.

Concept introduction:

Wolff Kishner Reduction is a reaction in which aldehydes and ketones are converted into alkanes on reaction with hydrazine, $\text{KOH}$, and on heating. Carbonyl compound is condensed on heating with hydrazine to form hydrazone. The base, $\text{KOH}$ reduces the carbon into alkane and oxidizes the hydrazine to nitrogen gas.

Answer to Problem 11.61AP

The synthesis of the given compound is shown below.

Explanation of Solution

The reaction of cyclopentenyl methanol with $\text{PCC}$ to forms an aldehyde. Further, the aldehyde undergoes Wolf-Kishner reduction to form an alkene substituent. The hydroboration-oxidation of alkene forms the product with secondary alcohol group which upon oxidation with PCC forms the desired product as shown below.

Figure 12

Conclusion

The synthesis of the given compound is shown in Figure 12.

Interpretation Introduction

(m)

Interpretation:

The synthesis of the given compound is to be drawn.

Concept introduction:

The substances which on addition removes oxygen atom or hydrogen atom from the other substance, that is, reduces the other substances are known as reducing agents. Reducing agents themselves get oxidized. Strong reducing agents like ${\text{NaBH}}_{\text{4}}$ reduces all the carbonyl groups present in a compound into alcohol.

Answer to Problem 11.61AP

The synthesis of the given compound is shown below.

Explanation of Solution

The alcohol is reduced in presence of ${\text{NaBH}}_{\text{4}}$ to form an aldehyde followed by the epoxidation of the double bond in presence of m CPBA to form the desired product as shown below.

Figure 13

Conclusion

The synthesis of the given compound is shown in Figure 13.