Chapter 14, Problem 14.37P

Interpretation Introduction

Interpretation:

The reagents and experimental condition should be shown to synthesize each compound given in the diagram from 1-propanol.

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Answer to Problem 14.37P

1. Dehydration- $\text{Conc}{\text{. H}}_{\text{2}}{\text{SO}}_{\text{4}}$ at $180{}^{\circ }\text{C}$
2. Hydration- dil. ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$
3. Oxidation- ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}{\text{, H}}_{\text{2}}{\text{SO}}_{\text{4}}$
4. Hydrobromination- HBr
5. Bromination- ${\text{Br}}_{\text{2}}$
6. Hydrogenation- ${\text{H}}_{\text{2}}\text{, Pt/Pd}$
7. Oxidation- ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}{\text{, H}}_{\text{2}}{\text{SO}}_{\text{4}}$
8. Oxidation- ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}{\text{, H}}_{\text{2}}{\text{SO}}_{\text{4}}$
9. Oxidation- ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}{\text{, H}}_{\text{2}}{\text{SO}}_{\text{4}}$

Explanation of Solution

The reactions which are involved to synthesize each molecule are shown in the below diagram:

The reagents and experimental condition for each reaction are described below:

1. Alcohols get converted into their corresponding alkenes through dehydration reaction. Water is formed from the hydroxyl group and hydrogen in the adjacent carbon. Primary alcohols get dehydrated at higher temperatures and in the presence of a strong acid, like sulfuric acid.



2. The hydration of an alkene in the presence of an acid like sulfuric acid puts the secondary alcohol in accordance with Markovnikov’s rule. According to the Markovnikov’s rule, the proton of the reagents gets added to the least substituted carbon while the remaining part of the reagent gets added to the most substituted carbon.



3. The oxidation of a secondary alcohol by using potassium dichromate and sulfuric acid gives the corresponding ketone.



4. The hydrobromination of an alkene by using hydrogen bromide puts the corresponding 2-bromopropane in accordance with Markovnikov’s rule. According to the Markovnikov’s rule, the proton of the reagent gets added to the least substituted carbon while the remaining part of the reagent gets added to the most substituted carbon.



5. The bromination of an alkene with bromine gives vicinal dibromo alkanes.



6. The hydrogenation of an alkene with hydrogen in the presence of a catalyst, like raney nickel, palladium or platinum, at a high temperature and pressure gives the corresponding alkane.



7. The oxidation of a primary alcohol by using potassium dichromate and sulfuric acid gives corresponding carboxylic acid. An intermediate aldehyde is formed in the reaction and is converted into corresponding carboxylic acid if it is not distilled out from the reaction mixture.



8. The oxidation of a primary alcohol by using potassium dichromate and sulfuric acid gives an aldehyde and should be distilled out from the reaction mixture to avoid getting further converted into the corresponding carboxylic acid.



9. The oxidation of an aldehyde by using potassium dichromate and sulfuric acid gives the corresponding carboxylic acid.

Conclusion

Thus, the process and reagent used are as follows:

1. Dehydration- $\text{Conc}{\text{. H}}_{\text{2}}{\text{SO}}_{\text{4}}$ at $180{}^{\circ }\text{C}$
2. Hydration- dil. ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$
3. Oxidation- ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}{\text{, H}}_{\text{2}}{\text{SO}}_{\text{4}}$
4. Hydrobromination- HBr
5. Bromination- ${\text{Br}}_{\text{2}}$
6. Hydrogenation- ${\text{H}}_{\text{2}}\text{, Pt/Pd}$
7. Oxidation- ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}{\text{, H}}_{\text{2}}{\text{SO}}_{\text{4}}$
8. Oxidation- ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}{\text{, H}}_{\text{2}}{\text{SO}}_{\text{4}}$
9. Oxidation- ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}{\text{, H}}_{\text{2}}{\text{SO}}_{\text{4}}$