Q. 12.32 - An Introduction to General, Organic, and Biological Chemistry

Question

Draw the condensed structural formulas for the aldehyde and carboxylic acid produced when each of the following is oxidized:

Step-by-Step Solution

Answer

a. ${\mathrm{C}}_4{\mathrm{H}}_7-{\mathrm{CH}}_2-\mathrm{OH} \left(\mathrm{Cyclobutylmethanol}\right)$ first oxidized to ${\mathrm{C}}_4{\mathrm{H}}_7-\mathrm{CHO} (\mathrm{Cyclobutyl}-\mathrm{methanal})$ and it further oxidized to ${\mathrm{C}}_4{\mathrm{H}}_7-\mathrm{COOH} (\mathrm{Cyclobutyl}-\mathrm{methanoic} \mathrm{acid})$.

b. ${\mathrm{CH}}_3-\mathrm{OH} \left(\mathrm{Methanol}\right)$ first oxidized to $\mathrm{HCHO} \left(\mathrm{Methanal}\right)$ and it further oxidized to $\mathrm{HCOOH} (\mathrm{Methanoic} \mathrm{acid})$.

c. ${\mathrm{CH}}_2\mathrm{Cl}-{\mathrm{CH}}_2-{\mathrm{CH}}_2\mathrm{OH} ( 3-\mathrm{chloro}-1-\mathrm{propanol})$ first oxidized to ${\mathrm{CH}}_2\mathrm{Cl}-{\mathrm{CH}}_2-\mathrm{CHO} (3-\mathrm{Chloro}-1-\mathrm{propanal})$ and it further oxidized to ${\mathrm{CH}}_2\mathrm{Cl}-{\mathrm{CH}}_2-\mathrm{COOH} (3-\mathrm{Chloro}-1-\mathrm{propanoic} \mathrm{acid})$.

Part(a) Step 1: Given information

We need to draw the condensed structural formula for the aldehyde and carboxylic acid produced when Cyclobutyl-methanol is oxidized.

Part(a) Step 2: Explanation

In organic chemistry, alcohol oxidation is a crucial process. Aldehydes and carboxylic acids can be made by oxidizing primary alcohols. 

Given, ${\mathrm{C}}_4{\mathrm{H}}_7-{\mathrm{CH}}_2-\mathrm{OH} \left(\mathrm{Cyclobutylmethanol}\right)$ first oxidizes to ${\mathrm{C}}_4{\mathrm{H}}_7-\mathrm{CHO} (\mathrm{Cyclobutyl}-\mathrm{methanal})$and then oxidizes to ${\mathrm{C}}_4{\mathrm{H}}_7-\mathrm{COOH} (\mathrm{Cyclobutyl}-\mathrm{methanoic} \mathrm{acid})$.

Part(b) Step 1: Given information

We need to draw the condensed structural formula for the aldehyde and carboxylic acid produced when ${\mathrm{CH}}_3-\mathrm{OH}$ is oxidized.

Part(b) Step 2: Explanation

In organic chemistry, alcohol oxidation is a crucial process. Aldehydes and carboxylic acids can be made by oxidizing primary alcohols. 

Given, ${\mathrm{CH}}_3-\mathrm{OH} \left(\mathrm{Methanol}\right)$ oxidizes to $\mathrm{HCHO} \left(\mathrm{Methanal}\right)$.

Methanal oxidizes to $\mathrm{HCOOH} (\mathrm{Methanoic} \mathrm{acid})$.

Part(c) Step 1: Given information

We need to draw the condensed structural formula for the aldehyde and carboxylic acid produced when $3-\mathrm{chloro}-1-\mathrm{propanol}$ is oxidized.

Part(c) Step 2: Explanation

In organic chemistry, alcohol oxidation is a crucial process. Aldehydes and carboxylic acids can be made by oxidizing primary alcohols. 

Given, ${\mathrm{CH}}_2\mathrm{Cl}-{\mathrm{CH}}_2-{\mathrm{CH}}_2\mathrm{OH} ( 3-\mathrm{chloro}-1-\mathrm{propanol})$ oxidizes to ${\mathrm{CH}}_2\mathrm{Cl}-{\mathrm{CH}}_2-\mathrm{CHO} (3-\mathrm{Chloro}-1-\mathrm{propanal})$ and it further oxidizes to ${\mathrm{CH}}_2\mathrm{Cl}-{\mathrm{CH}}_2-\mathrm{COOH} (3-\mathrm{Chloro}-1-\mathrm{propanoic} \mathrm{acid})$.