Question of 87
Q.Describe the following :
(i) Acetylation
(ii) Cannizaro reaction
(iii) Cross aldol condensation
(iv) Decarboxylation
Andhra Pradesh BieapBIEAP Intermediate Board 2019Subjective· 8mImportance★★★★★
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Start your 14-day free trial to unlock the full solution →These are four classic named reactions/processes of carbonyl and carboxylic-acid chemistry.
- Acetylation: The introduction of an acetyl group (CH₃CO–) into an organic molecule, usually replacing an active hydrogen atom of an –OH or –NH₂ group, using an acetylating agent such as acetic anhydride or acetyl chloride. Example: Salicylic acid + acetic anhydride → Aspirin (acetylsalicylic acid) + acetic acid. Acetylation is used, for example, to reduce the side effects/increase the potency of certain drugs, and to protect –OH/–NH₂ groups from unwanted reactions.
- Cannizzaro reaction: Aldehydes that lack an α-hydrogen (and so cannot undergo aldol condensation) undergo a self oxidation–reduction (disproportionation) reaction when treated with concentrated NaOH or KOH: one molecule of the aldehyde is reduced to the corresponding alcohol while another is simultaneously oxidised to the carboxylate salt. General: 2RCHO (no α-H) + conc. NaOH → RCH₂OH + RCOONa Example: 2HCHO + conc. NaOH → CH₃OH + HCOONa (Also, e.g., 2C₆H₅CHO + conc. NaOH → C₆H₅CH₂OH + C₆H₅COONa)
- Cross aldol condensation: An aldol condensation carried out between two different aldehydes and/or ketones (at least one of which has an α-hydrogen), catalysed by dilute acid or base. Since either carbonyl compound can act as the nucleophile (enolate) or the electrophile, a mixture of possible β-hydroxy carbonyl products (which can dehydrate to α,β-unsaturated carbonyl compounds) is obtained, unless one partner has no α-hydrogen (which then reduces the mixture to fewer, more predictable products). Example: CH₃CHO + CH₃COCH₃ --(dil. NaOH)--> a mixture of cross-aldol products.
- Decarboxylation: …
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