Question

Using appropriate reactants, alcohols can be oxidized into aldehydes, ketones, and/or carboxylic acids. Primary alcohols can be oxidized into aldehydes, which can then be oxidized into carboxylic acids. Secondary alcohols can be oxidized into ketones. Tertiary alcohols do not undergo this type of oxidation. Give the structure of the product(s) resulting from the oxidation of each of the following alcohols.

Short answer

(a) The Products are 3 -methylbutanal and 3-methylbutanoic acid

(b)The given alcohol is secondary, and its oxidation product will be ketone "3-methyl-2-butanone"

(c)The given alcohol is a tertiary alcohol and is not able to initiate the oxidation process.

(d)The given alcohol is primary and its oxidation product will be aldehyde "benzaldehyde" and can further oxidized to carboxylic acid called "benzoic acid".

(e) The given alcohol is secondary, and its oxidation product will be ketone "2-methyl-cyclohexanone".

(f) The given alcohol is a primary type, and its oxidation product will be carboxylic acid "2-hydroxy-2-methyl-3oxocyclohexanecarboxylic acid".

Step-by-step solution

Step 1:3-methyl-1-butanol

The oxidation reaction is shown in the picture below. Two products namely aldehyde (3methylbutanal) and carboxylic acid (3-methylbutanoic acid) are formed. This alcohol is primary because a hydroxyl group is attached to the carbon atom that has two hydrogen atoms and no other substitutes. In the first step, the primary alcohol will be oxidized to aldehyde. Hydrogen atoms from the hydroxyl group and the carbon atom will form a water molecule. In the second step, an additional oxygen atom will form the bond with the carbon atom creating a new hydroxylic group that will be a part of the carboxylic acid group. As a result, carboxylic acid is formed.

Hence the Products are 3 -methylbutanal and 3-methylbutanoic acid

3-methyl-2-butanol:

The given alcohol "3-methyl-2-butanol" is the secondary alcohol.

Therefore, bond between hydrogen and oxygen is broken during the oxidation process. ,while the electron density of hydrogen is shifted towards oxygen atom forming negative charge on oxygen atom and Free orbitals will then form a double bond between oxygen and a carbon atom giving aldehyde as the final product.

Because of this the product will be a ketone.

Hence the given alcohol is secondary, and its oxidation product will be ketone "3-methyl-2-butanone".

2-methyl-2-butanol:

The given alcohol "2-methyl-2-butanol" is the tertiary alcohol.

Therefore, after observing the given alcohol following conclusion are drawn that the oxidation is not possible because both oxygen and carbon atoms are attached to the third carbon atom in the chain.

Hence The given alcohol is a tertiary alcohol and is not able to start the oxidation process.

Benzyl alcohol:

The given alcohol "benzyl alcohol" is the primary alcohol. Therefore, bond between hydrogen and oxygen is broken during the oxidation process. ,while the electron density of hydrogen is shifted towards oxygen atom forming negative charge on oxygen atom and Free orbitals will then form a double bond between oxygen and a carbon atom giving aldehyde as the final product.

Hence The given alcohol is primary, and its oxidation product will be aldehyde "benzaldehyde" and can further become carboxylic acid "benzoic acid".

2-methyl-cyclohexanol

The given alcohol "2-methyl-cyclohexanol" is the secondary alcohol.Therefore, bond between hydrogen and oxygen is broken during the oxidation process. ,while the electron density of hydrogen is shifted towards oxygen atom forming negative charge on oxygen atom and Free orbitals will then form a double bond between oxygen and a carbon atom giving aldehyde as the final product.

Because of this the product will be a ketone.

Hence The given alcohol is secondary, and its oxidation product will be ketone "2-methyl-cyclohexanone".

6-(hydroxymethyl)-1-methylcyclohexane-1,2-diol

The given alcohol "6-(hydroxymethyl)-1-methylcyclohexane-1,2-diol" is a primary alcohol. Therefore, bond between hydrogen and oxygen is broken during the oxidation process. , while the electron density of hydrogen is shifted towards oxygen atom forming negative charge on oxygen atom and Free orbitals will then form a double bond between oxygen and a carbon atom giving aldehyde as the final product.

This will happen with the first and second alcohol group.

Since the product is an aldehyde hence there is a possibility for one more oxidation,

Next, oxygen atom gets attached to the hydrogen atom that is directly bonded to the second carbonyl group. Because of this the product will be a carboxylic acid

Hence The given alcohol is a primary type and its oxidation product will be carboxylic acid "2-hydroxy-2-methyl-3oxocyclohexanecarboxylic acid".