Chapter 23, Problem 51A

Interpretation Introduction

Interpretation: To explain why 2-methyl-1-propanol can be oxidized and 2-methyl-2-propanol cannot be oxidized.

Concept Introduction: Oxidation of alcohols will lead to the formation of aldehydes. The formation of carbocations will decide which compound will form an aldehyde. Primary and secondary carbocation can form the alcohols and tertiary carbocation cannot form the alcohols as they do not have hydrogen.

Answer to Problem 51A

2-methyl-1-propanol will form primary carbocation and 2-methyl-2-propanol will form a tertiary carbocation. Therefore, 2-methyl-2-propanol cannot be oxidized and 2-methyl-1-propanol can be oxidized.

Explanation of Solution

2-methyl-1-propanol will form primary carbocation and 2-methyl-2-propanol will form a tertiary carbocation. Primary carbocation can easily be oxidized to aldehydes as there is hydrogen present. The carbon attached to the oxygen is also attached to hydrogen which results in the formation of aldehyde. Tertiary carbocation cannot be oxidized aldehydes because there is no hydrogen present. The carbon attached to the oxygen is not attached to the hydrogen but it is attached to other carbons which makes it difficult to oxidize.

Conclusion

Only primary and secondary alcohols can be oxidized to form aldehydes and ketones. Tertiary alcohols cannot undergo oxidation because of the absence of hydrogen in the tertiary carbocation which does not allow oxidation.