Chapter 21, Problem 21.85P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the given compound is to be shown.

Concept introduction:

The acetic acid is treated with various reagents to form products that contain different functional groups. The new functional groups formed are anhydride, amine, ether, aldehyde, ketone, etc. When carboxylic acid converted to an acid anhydride, the stability ladder going up. When an anhydride reacted with ethanol to formed the ester, the stability ladder going down.

Answer to Problem 21.85P

The synthesis of the given compound is as follows:

Explanation of Solution

The reaction requires converting a carboxylic acid to an acid anhydride, which represents going up the stability ladder. This is difficult to do directly but can be carried out by first producing an acid chloride. The acid chloride and the salt of acetic acid will make the desired anhydride.

Conclusion

The acetic acid is treated with various reagents to form products that contain different functional groups.

Interpretation Introduction

(b)

Interpretation:

The synthesis of the given compound is to be shown.

Concept introduction:

The acetic acid is treated with various reagents to form products that contain different functional groups. The new functional groups formed are anhydride, amine, ether, aldehyde, ketone, etc. When carboxylic acid converted to an acid anhydride, the stability ladder going up. When an anhydride reacted with ethanol to formed the ester, the stability ladder going down.

Answer to Problem 21.85P

The synthesis of the given compound is as follows:

Explanation of Solution

The addition of phenol forms the ester under acidic condition, a Fischer esterification. This is a reversible reaction and can be carried out directly because the reactant and product species are on the same rung of the stability ladder.

Conclusion

The acetic acid is treated with various reagents to form products that contain different functional groups.

Interpretation Introduction

(c)

Interpretation:

The synthesis of the given compound is to be shown.

Concept introduction:

The acetic acid is treated with various reagents to form products that contain different functional groups. The new functional groups formed are anhydride, amine, ether, aldehyde, ketone, etc. When carboxylic acid converted to an acid anhydride, the stability ladder going up. When an anhydride reacted with ethanol to formed the ester, the stability ladder going down.

Answer to Problem 21.85P

The synthesis of the given compound is as follows,

Explanation of Solution

The reaction of the anhydride from (a) with ethanol makes the ester. This represents going down the stability ladder and is done relatively easily.

Conclusion

The acetic acid is treated with various reagents to form products that contain different functional groups.

Interpretation Introduction

(d)

Interpretation:

The synthesis of the given compound is to be shown.

Concept introduction:

The acetic acid is treated with various reagents to form products that contain different functional groups. The new functional groups formed are anhydride, amine, ether, aldehyde, ketone, etc. When carboxylic acid converted to an acid anhydride, the stability ladder going up. When an anhydride reacted with ethanol to formed the ester, the stability ladder going down.

Answer to Problem 21.85P

The synthesis of the given compound is as follows:

Explanation of Solution

The amine can be produced by reducing the corresponding amide. It is difficult to produce the amide directly from acetic acid because the amine that would be required for the nucleophile would deprotonate the carboxylic acid. The amide can be made relatively easily, however, by first converting acetic acid to acetyl chloride and then treating acetyl chloride with the amine.

Conclusion

The acetic acid is treated with various reagents to form products that contain different functional groups.

Interpretation Introduction

(e)

Interpretation:

The synthesis of the given compound is to be shown.

Concept introduction:

The acetic acid is treated with various reagents to form products that contain different functional groups. The new functional groups formed are anhydride, amine, ether, aldehyde, ketone, etc. When carboxylic acid converted to an acid anhydride, the stability ladder going up. When an anhydride reacted with ethanol to formed the ester, the stability ladder going down.

Answer to Problem 21.85P

The synthesis of the given compound is as follows,

Explanation of Solution

Reducing the acid to an alcohol, followed by dehydration, leads to the ether. Alternatively, ethanol can be deprotonated by $\text{NaH}$ to produce ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{OH-}$, which could then be reacted with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{Br}$ in a Williamson ether synthesis.

Conclusion

The acetic acid is treated with various reagents to form products that contain different functional groups.

Interpretation Introduction

(f)

Interpretation:

The synthesis of the given compound is to be shown.

Concept introduction:

The acetic acid is treated with various reagents to form products that contain different functional groups. The new functional groups formed are anhydride, amine, ether, aldehyde, ketone, etc. When carboxylic acid converted to an acid anhydride, the stability ladder going up. When an anhydride reacted with ethanol to formed the ester, the stability ladder going down.

Answer to Problem 21.85P

The synthesis of the given compound is as follows,

Explanation of Solution

First, acid is treated with ${\text{SOCl}}_{\text{2}}$ to produce an acid chloride. The acid chloride plus the specialized agent, $\text{LiAlH}{\left(\text{O-tBu}\right)}_{\text{3}}$, forms the aldehyde.

Conclusion

The acetic acid is treated with various reagents to form products which contain different functional groups.

Interpretation Introduction

(g)

Interpretation:

The synthesis of the given compound is to be shown.

Concept introduction:

The acetic acid is treated with various reagents to form products that contain different functional groups. The new functional groups formed are anhydride, amine, ether, aldehyde, ketone, etc. When carboxylic acid converted to an acid anhydride, the stability ladder going up. When an anhydride reacted with ethanol to formed the ester, the stability ladder going down.

Answer to Problem 21.85P

The synthesis of the given compound is as follows,

Explanation of Solution

First, acid is treated with ${\text{SOCl}}_{\text{2}}$ to produce an acid chloride. The acid chloride is treated with lithium dialkylcuprate forms the ketone.

Conclusion

The acetic acid is treated with various reagents to form products which contain different functional groups.