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Which of the following is least reactive towards a nucleophilic attack?(a) Acetaldehyde(b) Butanone(c) Diisopropyl ketone(d) Ditert-Butyl ketoneThe question was asked during an interview.My doubt stems from Aldehydes and Ketones Chemical Reactions in section Aldehydes, Ketones and Carboxylic Acids of Chemistry – Class 12

Answer»

Right answer is (d) Ditert-Butyl ketone

For explanation: The STEARIC EFFECTS come into consideration when comparing these compounds. Ditert-Butyl ketone has two very BULKY tert-butyl groups, one on EITHER side of the carbonyl carbon. This increases the hinderance to the INCOMING nucleophile and decreases the reactivity.



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