Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Aldehydes, Ketones and Carboxylic Acids

Question:

Read the Passage carefully and answer the Questions.

Carbonyl compounds such as aldehydes, ketones, and carboxylic acids play an important role in the biochemical process of plants and animal kingdom. Many aldehydes and ketones find applications in dye, perfumery and other industries. The carbonyl carbon atom is $sp^2$-hybridized forming three sigma and one pi-bond with oxygen. C-O bonds are polar bond due to high electronegativity of oxygen than carbon. Hence the carbonyl carbon behaves as an electrophilic center and oxygen as a nucleophilic centre. Primary and secondary alcohols yield aldehydes and ketones respectively upon oxidation with variety of oxidizing agents. The boiling points of aldehydes and ketones differ from hydrocarbons and ethers. Aldehydes and ketones undergo nucleophilic addition reaction due to presence of electrophilic carbonyl carbon. Nucleophile and a proton add across the carbon oxygen double bond.

The alcohol which cannot be used to prepare carbonyl compound through oxidation is

Options:

$CH_3CH_2CH_2CH_2OH$

$(CH_3)_3C-OH$

$CH_3CH_2CH(OH)CH_3$

$CH_3CH=CHCH_2OH$

Correct Answer:

$(CH_3)_3C-OH$

Explanation:

The correct answer is Option (2) → $(CH_3)_3C-OH$ **

  • Primary alcohols → oxidize to aldehydes / acids
    • CH₃CH₂CH₂CH₂OH ✔
    • CH₃CH=CHCH₂OH ✔
  • Secondary alcohols → oxidize to ketones
    • CH₃CH₂CH(OH)CH₃ ✔
  • Tertiary alcoholsdo not undergo oxidation to carbonyl compounds because they lack a hydrogen atom on the carbon bearing –OH.

Therefore, tert-butanol ((CH₃)₃C–OH) cannot be used to prepare a carbonyl compound through oxidation.