Q. 12.31 - 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. ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{OH} (1-\mathrm{Pentanol})$ first oxidized to ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{CHO} (1-\mathrm{Pentanal})$ and it further oxidized to ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{COOH} (1-\mathrm{Pentanoic} \mathrm{acid})$.

b. ${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{OH} (3-\mathrm{Methylbutane}-1-\mathrm{ol})$ first oxidizes to ${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-{\mathrm{CH}}_2-\mathrm{CHO} (3-\mathrm{Methylbutane}-1-\mathrm{al})$ and then to ${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-{\mathrm{CH}}_2-\mathrm{COOH} (3-\mathrm{Methyl}-1-\mathrm{butanoic} \mathrm{acid})$.

c. ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{OH} (1-\mathrm{Butanol})$ first oxidizes to ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{CHO} (1-\mathrm{Butanal})$ and further oxidizes to ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{COOH} (1-\mathrm{Butanoic} \mathrm{acid})$

Part(a) Step 1: Given information

We need to draw the condensed structural formula for the aldehyde and carboxylic acid produced when the following is oxidized: 

${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{OH}$

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, ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{OH} (1-\mathrm{Pentanol})$first oxidized to ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{CHO} (1-\mathrm{Pentanal})$ and it further oxidized to ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{COOH} (1-\mathrm{Pentanoic} \mathrm{acid})$.

Part(b) Step 1: Given information

We need to draw the condensed structural formula for the aldehyde and carboxylic acid produced when the following is oxidized: 

${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{OH}$

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, ${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{OH} (3-\mathrm{Methylbutane}-1-\mathrm{ol})$ first oxidizes to ${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-{\mathrm{CH}}_2-\mathrm{CHO} (3-\mathrm{Methylbutane}-1-\mathrm{al})$ and then to ${\mathrm{CH}}_3-\mathrm{CH}\left({\mathrm{CH}}_3\right)-{\mathrm{CH}}_2-\mathrm{COOH} (3-\mathrm{Methyl}-1-\mathrm{butanoic} \mathrm{acid})$.

Part(c) Step 1: Given information

We need to draw the condensed structural formula for the aldehyde and carboxylic acid produced when the following is oxidized: 

${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{OH} (1-\mathrm{butanol})$

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, ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{OH} (1-\mathrm{Butanol})$ first oxidizes to ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{CHO} (1-\mathrm{Butanal})$ and further oxidizes to ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{CH}}_2-\mathrm{COOH} (1-\mathrm{Butanoic} \mathrm{acid})$.