Q53E - Chemistry (OpenStax)

Question

Alcohols\(A,B\) , and \(C\) all have the composition \({C_4}{H_{10}}O.\) Molecules of alcohol A contain a branched carbon chain and can be oxidized to an aldehyde; molecules of alcohol B contain a linear carbon chain and can be oxidized to a ketone; and molecules of alcohol C can be oxidized to neither an aldehyde nor a ketone. Write the Lewis structures of these molecules.

 

Step-by-Step Solution

Answer

a) 2-methyl-l-propanol

b) 2-propanol

c) tert-butyl alcohol

Step 1: 2-methyl-1-propanol

Compound A.

It says that its molecular formula is \({C_4}{H_{10}}O\) and that it can be oxidized to an aldehyde

Only primary alcohols can be oxidized to aldehydes.

Also, it says that it contains a branch, meaning there is a methyl group on carbon 2 on the propane chain.

It's 2-methyl-1-propanol.

         Compound A

Step 2: 2-butanol

Compound B.

It is oxidized to ketone and has a straight chain and the same molecular formula as A.

This means that it's secondary alcohol because only they can form ketones by oxidation

It's 2-butanol

             Compound B

Step 3: The tert-butyl alcohol

Compound C.

It says that it cannot be oxidized and has the same molecular formula as \(A\) and \(B.\) 

Only tertiary alcohols cannot be oxidized.

Therefore, the compound we are searching for is tert-butyl alcohol.

                 Compound C