Chapter 20, Problem 20.15P

What product is formed when ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ is treated with each reagent:

(a) ${\text{H}}_{\text{2}}$ ( $1$ equiv), $\text{Pd-C}$; (b) ${\text{H}}_{\text{2}}$ ( $2$ equiv), $\text{Pd-C}$; (c) ${\text{LiAlH}}_{\text{4}}$, followed by ${\text{H}}_{\text{2}}\text{O}$; (d) ${\text{NaBH}}_{\text{4}}$, ${\text{CH}}_{\text{3}}\text{OH}$?

Interpretation Introduction

(a)

Interpretation: The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is to be predicted.

Concept introduction: Alkenes on hydrogenation reaction in the presence of $\text{Pd-C}$ converts into alkane. Aldehyde and ketone on hydrogenation reaction gives primary and secondary alcohol, respectively.

Answer to Problem 20.15P

The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is,

Figure 1

Explanation of Solution

The given compound ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ contains three functional groups, alkene, ketone and ester. Alkene on reaction with one equivalent of ${\text{H}}_{\text{2}}$, converts into alkane. The $\text{C}=\text{C}$ becomes $\text{C}-\text{C}$ on reaction with one equivalent of ${\text{H}}_{\text{2}}$. The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with one equivalent of ${\text{H}}_{\text{2}}$ is shown in Figure 2.

Figure 2

Conclusion

The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is to be predicted.

Concept introduction: Alkenes on hydrogenation reaction in the presence of $\text{Pd-C}$ converts into alkane. Aldehyde and ketone on hydrogenation reaction gives primary and secondary alcohol, respectively.

Answer to Problem 20.15P

The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is,

Figure 3

Explanation of Solution

The given compound ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ contains three functional groups, alkene, ketone and ester. The first equivalent of ${\text{H}}_{\text{2}}$ converts $\text{C}=\text{C}$ (alkene) to $\text{C}-\text{C}$ (alkane) through hydrogenation. The second equivalent of ${\text{H}}_{\text{2}}$ convertsketone group of the given compound to secondary alcohol. The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with two equivalents of ${\text{H}}_{\text{2}}$ is shown in Figure 4.

Figure 4

Conclusion

The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is shown in Figure 4.

Interpretation Introduction

(c)

Interpretation: The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is to be predicted.

Concept introduction: Alkenes on hydrogenation reaction in the presence of $\text{Pd-C}$ converts into alkane. Aldehyde and ketone on reduction with ${\text{LiAlH}}_{\text{4}}$ give primary and secondary alcohol, respectively.

Answer to Problem 20.15P

The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is,

Figure 5

Explanation of Solution

The given compound ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ contains three functional groups, alkene, ketone and ester. Lithium aluminiumhydride is a strong reducing agent. It reduces ketone and ester to secondary and primary alcohol, respectively. However, it does not with $\text{C}=\text{C}$ carbon atoms. The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with ${\text{LiAlH}}_{\text{4}},{\text{H}}_{\text{2}}\text{O}$ is shown in Figure 6.

Figure 6

Conclusion

The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is shown in Figure 6.

Interpretation Introduction

(d)

Interpretation: The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is to be predicted.

Concept introduction: Alkenes on hydrogenation reaction in the presence of $\text{Pd-C}$ converts into alkane. Aldehyde and ketone on reduction with ${\text{LiAlH}}_{\text{4}}$ give primary and secondary alcohol, respectively.

Answer to Problem 20.15P

The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is,

Figure 7

Explanation of Solution

The given compound ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ contains three functional groups, alkene, ketone and ester. Sodium borohydride is a moderate reducing agent. It reduces ketone to secondary alcohol but it cannot reduce ester and alkene. The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with ${\text{NaBH}}_{\text{4}},{\text{CH}}_{\text{3}}\text{OH}$ is shown in Figure 8.

Figure 8

Conclusion

The product formed by the treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}={\text{CHCH}}_{\text{2}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with the given reagent is shown in Figure 8.