Chapter 17, Problem 40P

Interpretation Introduction

(a)

Interpretation: The product formed when the $\text{α},\text{β}-$ unsaturated ketone A is treated with the ${\text{NaBH}}_{\text{4}}$, ${\text{CH}}_{\text{3}}\text{OH}$ is to be predicted.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Interpretation Introduction

(b)

Interpretation: The product formed when the $\text{α},\text{β}-$ unsaturated ketone A is treated with the ${\text{H}}_2\left(1\text{equiv}\right)$, $\text{Pd}-\text{C}$ is to be predicted.

Concept introduction: Addition of hydrogen takes place across a double bond of alkenes to form alkanes. This process is known as hydrogenation. It takes place in the presence of catalysts such as nickel, platinum or palladium.

Interpretation Introduction

(c)

Interpretation: The product formed when the $\text{α},\text{β}-$ unsaturated ketone A is treated with the ${\text{H}}_2\left(\text{excess}\right)$, $\text{Pd}-\text{C}$ is to be predicted.

Concept introduction: Addition of hydrogen takes place across a double bond of alkenes to form alkanes. This process is known as hydrogenation. It takes place in the presence of catalysts such as nickel, platinum or palladium.

Interpretation Introduction

(d)

Interpretation: The product formed when the $\text{α},\text{β}-$ unsaturated ketone A is treated with the $\left[1\right]{\text{CH}}_{\text{3}}\text{Li}$;$\left[\text{2}\right]{\text{H}}_{\text{2}}\text{O}$ is to be predicted.

Concept introduction: Methyllithium in the presence of water reduces carbonyl compounds into alcohol. Methyllithium is a reducing agent.

Interpretation Introduction

(e)

Interpretation: The product formed when the $\text{α},\text{β}-$ unsaturated ketone A is treated with the $\left[\text{1}\right]{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{MgBr}$, $\left[\text{2}\right]{\text{H}}_{\text{2}}\text{O}$ is to be predicted.

Concept introduction: Grignard reagent is prepared by the reaction of alkyl or aryl bromide with magnesium metal in the presence of ether. The reaction of Grignard reagent with an aldehyde/ketone followed by hydrolysis yields an alcohol.

Interpretation Introduction

(f)

Interpretation: The product formed when the $\text{α},\text{β}-$ unsaturated ketone A is treated with the $\left[\text{1}\right]{\left({\text{CH}}_{\text{2}}=\text{CH}\right)}_{\text{2}}\text{CuLi}$, $\left[\text{2}\right]{\text{H}}_{\text{2}}\text{O}$ is to be predicted.

Concept introduction: The steps involved in the reaction of ketone with organolithium reagent are as follows:

• The first step involves the reduction of carbonyl group into single bonds.

• The second step is the addition of R group from organometallic reagent and hydrogen to oxygen.