Q 39 E - Organic Chemistry (Mcmurry)

Question

Question:Which of the eight alcohols that you identified in Problem 17-38 react with ${\mathbf{CrO}}_{\mathbf{3}}$ in aqueous acid? Show the products you would expect from each reaction

Step-by-Step Solution

Answer

The reaction followed as:

Step 1: Reaction with chromic acid

Chromic acid is the reagent used to reduce the alcohol to carboxylic acid, aldehyde, and ketone.

Step 2: Isomer of C 5 H 12 O

Isomers of  ${\mathrm{C}}_5{\mathrm{H}}_{12}\mathrm{O}$ are given below. The compounds have the same molecular formula. The only difference is in their structure, that is, by changing the position of the hydroxy group and by branching the carbon chain as shown:

Step 3: Reaction of the isomer with chromic acid

Chromic acid converts primary alcohol into a carboxylic acid and secondary alcohol into ketone. The tertiary does not now show reaction like isomer 2-methyl-2-butanol as shown: