Chapter 20, Problem 20.34P

Draw the product when each compound is treated with either ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$, followed by ${\text{H}}_{\text{2}}\text{O}$, or $\text{HC}\equiv \text{CLi}$, followed by ${\text{H}}_{\text{2}}\text{O}$.

a. b. c.

Interpretation Introduction

(a)

Interpretation: The product formed by the treatment of given compound with either ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ or $\text{HC}\equiv \text{CLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ is to be stated.

Concept introduction: Organometallic reagents like $\text{RLi,}\text{RMgX}$ and ${\text{R}}_{\text{2}}\text{CuLi}$ are the source of ${\text{R}}^{-}$, which acts as a nucleophile. Organocuprate reagent form $1,4$-addition product on reaction with $\text{α},\text{β}$-unsaturated carbonyl compound whereas organolithium and Grignard reagent form $1,2$-addition product on reaction with $\text{α},\text{β}$-unsaturated carbonyl compound.

Answer to Problem 20.34P

The product formed by the treatment of given compound with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ and $\text{HC}\equiv \text{CLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ is,

Figure 1

Explanation of Solution

The given reagents are organocuprate $\left({\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}\right)$ and organolithium $\left(\text{HC}\equiv \text{CLi}\right)$. Organocuprate reagent form $1,4$-addition product whereas organolithium reagent form $1,2$-addition product on reaction with $\text{α},\text{β}$-unsaturated carbonyl compound.

The product formed by the reaction of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ with given $\text{α},\text{β}$-unsaturated carbonyl compound is $1,4$-addition product as shown in Figure 2.

Figure 2

The product formed by the reaction of $\text{HC}\equiv \text{CLi}$ with given $\text{α},\text{β}$-unsaturated carbonyl compound is $1,4$-addition product as shown in Figure 3.

Figure 3

Conclusion

The product formed by the treatment of given compound with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ and $\text{HC}\equiv \text{CLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ is shown in Figure 2 and Figure 3.

Interpretation Introduction

(b)

Interpretation: The product formed by the treatment of given compound with either ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ or $\text{HC}\equiv \text{CLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ is to be stated.

Concept introduction: Organometallic reagents like $\text{RLi,}\text{RMgX}$ and ${\text{R}}_{\text{2}}\text{CuLi}$ are the source of ${\text{R}}^{-}$, which acts as a nucleophile. Organocuprate reagent form $1,4$-addition product on reaction with $\text{α},\text{β}$-unsaturated carbonyl compound whereas organolithium and Grignard reagent form $1,2$-addition product on reaction with $\text{α},\text{β}$-unsaturated carbonyl compound.

Answer to Problem 20.34P

The product formed by the treatment of given compound with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ and $\text{HC}\equiv \text{CLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ is,

Figure 4

Explanation of Solution

The given reagents are organocuprate $\left({\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}\right)$ and organolithium $\left(\text{HC}\equiv \text{CLi}\right)$. Organocuprate reagent form $1,4$-addition product whereas organolithium reagent form $1,2$-addition product on reaction with $\text{α},\text{β}$-unsaturated carbonyl compound.

The product formed by the reaction of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ with given $\text{α},\text{β}$-unsaturated carbonyl compound is $1,4$-addition product as shown in Figure 5.

Figure 5

The product formed by the reaction of $\text{HC}\equiv \text{CLi}$ with given $\text{α},\text{β}$-unsaturated carbonyl compound is $1,4$-addition product as shown in Figure 6.

Figure 6

Conclusion

The product formed by the treatment of given compound with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ and $\text{HC}\equiv \text{CLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ is shown in Figure 5 and Figure 6.

Interpretation Introduction

(c)

Interpretation: The product formed by the treatment of given compound with either ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ or $\text{HC}\equiv \text{CLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ is to be stated.

Concept introduction: Organometallic reagents like $\text{RLi,}\text{RMgX}$ and ${\text{R}}_{\text{2}}\text{CuLi}$ are the source of ${\text{R}}^{-}$, which acts as a nucleophile. Organocuprate reagent form $1,4$-addition product on reaction with $\text{α},\text{β}$-unsaturated carbonyl compound whereas organolithium and Grignard reagent form $1,2$-addition product on reaction with $\text{α},\text{β}$-unsaturated carbonyl compound.

Answer to Problem 20.34P

The product formed by the treatment of given compound with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ and $\text{HC}\equiv \text{CLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ is,

Figure 7

Explanation of Solution

The given reagents are organocuprate $\left({\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}\right)$ and organolithium $\left(\text{HC}\equiv \text{CLi}\right)$. Organocuprate reagent form $1,4$-addition product whereas organolithium reagent form $1,2$-addition product on reaction with $\text{α},\text{β}$-unsaturated carbonyl compound.

The product formed by the reaction of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ with given $\text{α},\text{β}$-unsaturated carbonyl compound is $1,4$-addition product as shown in Figure 2.

Figure 8

The product formed by the reaction of $\text{HC}\equiv \text{CLi}$ with given $\text{α},\text{β}$-unsaturated carbonyl compound is $1,4$-addition product as shown in Figure 3.

Figure 9

Conclusion

The product formed by the treatment of given compound with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ and $\text{HC}\equiv \text{CLi}$ followed by ${\text{H}}_{\text{2}}\text{O}$ is shown in Figure 8 and Figure 9.