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🥼organic chemistry review

PCC

Written by the Fiveable Content Team • Last updated September 2025
Written by the Fiveable Content Team • Last updated September 2025

Definition

PCC, or Pyridinium Chlorochromate, is a versatile oxidizing agent used in organic chemistry for the selective oxidation of alcohols to aldehydes and ketones. This powerful reagent is widely employed in various reactions across multiple topics, including the hydration of alkynes, the oxidation of alcohols, and the preparation and oxidation of aldehydes and ketones.

5 Must Know Facts For Your Next Test

  1. PCC is a mild, selective oxidizing agent that can convert primary alcohols to aldehydes and secondary alcohols to ketones without over-oxidation to carboxylic acids.
  2. PCC is commonly used in the hydration of alkynes, where it can selectively oxidize the alkyne to an aldehyde or ketone.
  3. In the reactions of alcohols, PCC can be employed to oxidize alcohols to the corresponding carbonyl compounds (aldehydes or ketones).
  4. PCC plays a crucial role in the preparation of aldehydes and ketones, as it can selectively oxidize alcohols to the desired carbonyl products.
  5. PCC is also utilized in the oxidation of aldehydes and ketones, where it can further oxidize these compounds to carboxylic acids.

Review Questions

  • Explain how PCC is used in the hydration of alkynes to prepare aldehydes and ketones.
    • PCC is a versatile oxidizing agent that can be used in the hydration of alkynes to selectively convert the alkyne functional group to an aldehyde or ketone. The reaction involves the addition of water across the triple bond, followed by the oxidation of the resulting vinyl alcohol intermediate using PCC. This selective oxidation step ensures that the desired carbonyl product is obtained without over-oxidation to a carboxylic acid.
  • Describe the role of PCC in the reactions of alcohols, including the oxidation of primary and secondary alcohols.
    • PCC is a commonly used reagent for the oxidation of alcohols in organic chemistry. It can selectively convert primary alcohols to aldehydes and secondary alcohols to ketones, without further oxidation to carboxylic acids. This selectivity is a key advantage of PCC, as it allows for the controlled preparation of specific carbonyl compounds from alcohol precursors. The oxidation reactions involving PCC are widely employed in the synthesis of various organic molecules.
  • Discuss the importance of PCC in the preparation and oxidation of aldehydes and ketones, and how it relates to the use of aldol reactions in organic synthesis.
    • PCC plays a crucial role in the preparation of aldehydes and ketones, as it can selectively oxidize alcohols to the desired carbonyl products. This ability to generate aldehydes and ketones from alcohol precursors is essential for many organic synthesis strategies, including the use of aldol reactions. Aldol reactions, which involve the condensation of an aldehyde or ketone with another carbonyl compound, are widely employed in the synthesis of complex organic molecules. The availability of aldehydes and ketones prepared using PCC oxidation facilitates the execution of these important aldol transformations, ultimately enabling the construction of more elaborate molecular structures.